309:
33:
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1923:. In Nobel Prize-winning work, CFC's were shown to contribute to the depletion of atmospheric ozone. This discovery alerted the world to the negative consequences of organofluorine compounds and motivated the development of new routes to organofluorine compounds. In 2002, the first C-F bond-forming enzyme,
1646:
Some metal complexes cleave C-F bonds. These reactions are of interest from the perspectives of organic synthesis and remediation of xenochemicals. C-F bond activation has been classified as follows "(i) oxidative addition of fluorocarbon, (ii) M–C bond formation with HF elimination, (iii) M–C bond
189:
in polyfluorinated compounds. This is another reason for their high thermal stability. In addition, the fluorine substituents in polyfluorinated compounds efficiently shield the carbon skeleton from possible attacking reagents. This is another reason for the high chemical stability of polyfluorinated
169:
is one of the strongest in organic chemistry (an average bond energy around 480 kJ/mol). This is significantly stronger than the bonds of carbon with other halogens (an average bond energy of e.g. C-Cl bond is around 320 kJ/mol) and is one of the reasons why fluoroorganic compounds have high thermal
1514:
chemistry," exploits the concept of like-dissolves-like in the sense that fluorine-rich compounds dissolve preferentially in fluorine-rich solvents. Because of the relative inertness of the C-F bond, such fluorous phases are compatible with harsh reagents. This theme has spawned techniques of
1599:
overlap, the fluorination of organic ligands is used to tune the properties of component molecules. For example, the degree and regiochemistry of fluorination of metalated 2-phenylpyridine ligands in platinum(II) complexes significantly modifies the emission properties of the complexes.
638:. Asymmetric fluorination, whereby only one of two possible enantiomeric products are generated from a prochiral substrate, rely on electrophilic fluorination reagents. Illustrative of this approach is the preparation of a precursor to anti-inflammatory agents:
1906:
In 1957, the anticancer activity of 5-fluorouracil was described. This report provided one of the first examples of rational design of drugs. This discovery sparked a surge of interest in fluorinated pharmaceuticals and agrichemicals. The discovery of the
1014:-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor). Many of these display improved properties such as better safety profile, higher thermodynamic stability, ease of handling, high enantioselectivity, and selectivity over elimination side-reactions.
1884:(PTFE). Subsequent major developments, especially in the US, benefited from expertise gained in the production of uranium hexafluoride. Starting in the late 1940s, a series of electrophilic fluorinating methodologies were introduced, beginning with
299:
The structure of organofluorine compounds can be distinctive. As shown below, perfluorinated aliphatic compounds tend to segregate from hydrocarbons. This "like dissolves like effect" is related to the usefulness of fluorous phases and the use of
1261:. Introducing the carbon–fluorine bond to organic compounds is the major challenge for medicinal chemists using organofluorine chemistry, as the carbon–fluorine bond increases the probability of having a successful drug by about a factor of ten.
304:
in processing of fluoropolymers. In contrast to the aliphatic derivatives, perfluoroaromatic derivatives tend to form mixed phases with nonfluorinated aromatic compounds, resulting from donor-acceptor interactions between the pi-systems.
1651:
of fluorocarbon with M–F bond formation, (v) nucleophilic attack on fluorocarbon, and (vi) defluorination of fluorocarbon". An illustrative metal-mediated C-F activation reaction is the defluorination of fluorohexane by a zirconocene
279:
only contain carbon and fluorine. Sometimes they are called perfluorocarbons. They can be gases, liquids, waxes, or solids, depending upon their molecular weight. The simplest fluorocarbon is the gas tetrafluoromethane
156:
Fluorine has several distinctive differences from all other substituents encountered in organic molecules. As a result, the physical and chemical properties of organofluorines can be distinctive in comparison to other
1766:, respectively. Certain firearm lubricants such as "Tetra Gun" contain fluorocarbons. Capitalizing on their nonflammability, fluorocarbons are used in fire fighting foam. Organofluorine compounds are components of
1123:
has motivated the development of new methods for forming C–F bonds. Because of the short half-life of F, these syntheses must be highly efficient, rapid, and easy. Illustrative of the methods is the preparation of
882:
may appear to be an unlikely nucleophile, it is the most common source of fluoride in the synthesis of organofluorine compounds. Such reactions are often catalysed by metal fluorides such as chromium trifluoride.
1521:. Illustrative of fluorous technology is the use of fluoroalkyl-substituted tin hydrides for reductions, the products being easily separated from the spent tin reagent by extraction using fluorinated solvents.
1741:
and related alkene polymerization methodologies. The fluorinated substituents render the anions weakly basic and enhance the solubility in weakly basic solvents, which are compatible with strong Lewis acids.
184:
of the fluorine substituent is only 1.47 Ă…, which is shorter than in any other substituent and is close to that of hydrogen (1.2 Ă…). This, together with the short bond length, is the reason why there is no
532:
Organofluorine compounds are prepared by numerous routes, depending on the degree and regiochemistry of fluorination sought and the nature of the precursors. The direct fluorination of hydrocarbons with
432:
are colourless, high-melting crystalline solids, but the latter is a potent anti-cancer drug. The use of the C-F bond in pharmaceuticals is predicated on this altered reactivity. Several drugs and
2136:
Smith CE, Smith PS, Thomas RL, Robins EG, Collings JC, Dai C, et al. (2004). "Arene-perfluoroarene interactions in crystal engineering: structural preferences in polyfluorinated tolans".
284:). Liquids include perfluorooctane and perfluorodecalin. While fluorocarbons with single bonds are stable, unsaturated fluorocarbons are more reactive, especially those with triple bonds.
1954:. HFCs are potent greenhouse gases and are facing calls for stricter international regulation and phase out schedules as a fast-acting greenhouse emission abatement measure, as are
2323:
3430:
Heidelberger C, Chaudhuri NK, Danneberg P, Mooren D, Griesbach L, Duschinsky R, et al. (March 1957). "Fluorinated pyrimidines, a new class of tumour-inhibitory compounds".
2768:
2709:
Guo J, Kuang C, Rong J, Li L, Ni C, Hu J (May 2019). "Rapid
Deoxyfluorination of Alcohols with N-Tosyl-4-chlorobenzenesulfonimidoyl Fluoride (SulfoxFluor) at Room Temperature".
1989:
Because of the strength of the carbon–fluorine bond, many synthetic fluorocarbons and fluorocarbon-based compounds are persistent in the environment. Fluorosurfactants, such as
3539:
1073:, which is produced on a large-scale industrially via the intermediacy of difluorocarbene. The process begins with the thermal (600-800 °C) dehydrochlorination of
385:
Hydrofluorocarbons (HFCs), organic compounds that contain fluorine and hydrogen atoms, are the most common type of organofluorine compounds. They are commonly used in
222:
2280:
1758:, fluid fluoropolymers are used as specialty lubricants. Fluorocarbon-based greases are used in demanding applications. Representative products include Fomblin and
667:. The method is mainly used to perfluorinate, i.e. replace all C–H bonds by C–F bonds. The hydrocarbon is dissolved or suspended in liquid HF, and the mixture is
2084:
Lapasset J, Moret J, Melas M, Collet A, Viguier M, Blancou H (1996). "Crystal structure of 12,12,13,13,14,14,15,15,16,16,17,17,17-tridecafluoroheptadecan-1-ol, C
1809:, chloride, bromide, and iodide, only a handful of biologically synthesized carbon-fluorine bonds are known. The most common natural organofluorine species is
512:
Perfluorinated compounds are fluorocarbon derivatives, as they are closely structurally related to fluorocarbons. However, they also possess new atoms such as
186:
470:
As indicated throughout this article, fluorine-substituents lead to reactivity that differs strongly from classical organic chemistry. The premier example is
450:
In
September 2016, the so-called New York Declaration urged a global reduction in the use of HFCs. On 15 October 2016, due to these chemicals contribution to
1978:
1066:. The development of fluorous technologies (see below, under solvents) is leading to the development of reagents for the introduction of "fluorous tails".
296:, fluorocarbon-based compounds are sometimes used as lubricants or are highly volatile. Fluorocarbon liquids have medical applications as oxygen carriers.
1225:
The carbon-fluorine bond is commonly found in pharmaceuticals and agrochemicals because it is generally metabolically stable and fluorine acts as a
1022:
Many organofluorine compounds are generated from reagents that deliver perfluoroalkyl and perfluoroaryl groups. (Trifluoromethyl)trimethylsilane, CF
228:
between polyfluorinated molecules and is the reason for the often-observed boiling point reduction on fluorination as well as for the simultaneous
3587:
2169:
1734:
1561:
for monitoring reactions. The organofluorine compounds can serve as a "sigma-donor ligand," as illustrated by the titanium(III) derivative BPh
1848:
Organofluorine chemistry began in the 1800s with the development of organic chemistry. The first organofluorine compounds were prepared using
2013:
and may be harming the health of wildlife; the potential health effects of PFOA to humans are under investigation by the C8 Science Panel.
1903:. These new methodologies allowed the synthesis of C-F bonds without using elemental fluorine and without relying on metathetical methods.
1273:
used to administer some asthma medications. The current generation of propellant consists of hydrofluoroalkanes (HFA), which have replaced
617:. For this reason, alternative fluorination methodologies have been developed. Generally, such methods are classified into two classes.
288:
are more chemically and thermally stable than hydrocarbons, reflecting the relative inertness of the C-F bond. They are also relatively
3127:"Synthesis of Tris(2-Perfluorohexylethyl)tin Hydride: A Highly Fluorinated Tin Hydride with Advantageous Features of Easy Purification"
1286:
1010:
Apart from DAST, a wide variety of similar reagents exist, including, but not limited to, 2-pyridinesulfonyl fluoride (PyFluor) and
1149:
Biologically synthesized organofluorines have been found in microorganisms and plants, but not animals. The most common example is
17:
1981:
in global HCFC accounting and reduction. The U.S. and China at the same time announced a bilateral agreement to similar effect.
3346:
351:
Polymeric organofluorine compounds are numerous and commercially significant. They range from fully fluorinated species, e.g.
142:. The area of organofluorine chemistry often requires special techniques associated with the handling of fluorinating agents.
3236:
3203:
3170:
3105:
3072:
2625:
2593:
2216:
743:
The major alternative to electrophilic fluorination is nucleophilic fluorination using reagents that are sources of "F," for
910:
Notice that this transformation entails two reaction types, metathesis (replacement of Cl by F) and hydrofluorination of an
922:
455:
2641:
Aggarwal T, Verma AK (2021). "Achievements in fluorination using variable reagents through a deoxyfluorination reaction".
2233:
3580:
2419:
Caron S, Dugger RW, Ruggeri SG, Ragan JA, Ripin DH (July 2006). "Large-scale oxidations in the pharmaceutical industry".
1321:(PFOA) are two of the most studied because of their ubiquity, toxicity, and long residence times in humans and wildlife.
1157:
in at least 40 plants in
Australia, Brazil and Africa. Other biologically synthesized organofluorines include ω-fluoro
3035:"Mild and Selective Oxidation of Sulfur Compounds in Trifluorethanol: Diphenyl Disulfide and Methyle Phenyl Sulfoxide"
2199:
Siegemund G, Schwertfeger W, Feiring A, Smart B, Behr F, Vogel H, et al. (2005). "Fluorine
Compounds, Organic".
1837:
1450:
The development of organofluorine chemistry has contributed many reagents of value beyond organofluorine chemistry.
3540:"United States, China, and Leaders of G-20 Countries Announce Historic Progress Toward a Global Phase Down of HFCs"
1154:
3153:
Thompson ME, Djurovich PE, Barlow S, Marder S (2007). "Organometallic
Complexes for Optoelectronic Applications".
424:
behave similarly to the parent hydrocarbons, but their reactivity can be altered significantly. For example, both
1486:
group that stabilizes the negative charge. The triflate-group (the conjugate base of the triflic acid) is a good
1233:
atom. An estimated 1/5 of pharmaceuticals contain fluorine, including several of the top drugs. Examples include
458:
in Kigali, Rwanda reached a legally-binding accord to phase out hydrofluorocarbons (HFCs) in an amendment to the
3565:
1942:
Some organofluorine compounds pose significant risks and dangers to health and the environment. CFCs and HCFCs (
589:
Such reactions however are often unselective and require care because hydrocarbons can uncontrollably "burn" in
3573:
961:
521:
1169:
which are all believed to be biosynthesized in biochemical pathways from the intermediate fluoroacetaldehyde.
1107:
Sodium fluorodichloroacetate (CAS# 2837-90-3) is used to generate chlorofluorocarbene, for cyclopropanations.
2155:
2123:
57:
3008:
2766:
Le Bars D (2006). "Fluorine-18 and
Medical Imaging: Radiopharmaceuticals for Positron Emission Tomography".
1313:. Fluorosurfactants have low surface energies and dramatically lower surface tension. The fluorosurfactants
2010:
1920:
1779:
1612:
1314:
1120:
410:
2583:
405:. They do not harm the ozone layer as much as the compounds they replace; however, they do contribute to
364:
1603:
The coordination chemistry of organofluorine ligands also embraces fluorous technologies. For example,
4142:
4137:
4132:
4127:
4122:
4117:
4112:
4107:
4102:
4097:
4092:
4087:
4077:
4020:
3914:
3835:
3830:
3687:
1506:) confer distinctive solubility properties to molecules, which facilitates purification of products in
1170:
631:
Electrophilic fluorination rely on sources of "F". Often such reagents feature N-F bonds, for example
626:
1935:
Only a few organofluorine compounds are acutely bioactive and highly toxic, such as fluoroacetate and
1181:
Organofluorine chemistry impacts many areas of everyday life and technology. The C-F bond is found in
4178:
3880:
3850:
3840:
3820:
3808:
3776:
3741:
3709:
3677:
3672:
3632:
3408:
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1415:
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A special but significant application of the fluorinated building block approach is the synthesis of
884:
744:
67:
52:
4285:
4223:
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4213:
4208:
4203:
4198:
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4188:
4183:
4168:
4158:
4009:
3984:
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3929:
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3803:
3786:
3736:
3731:
3726:
3721:
3697:
3647:
3611:
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1550:
1419:
748:
507:
174:
166:
99:
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3714:
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1881:
1755:
1738:
1718:
1330:
398:
356:
336:), illustrating the donor-acceptor interactions between the fluorinated and nonfluorinated rings.
62:
47:
1973:
agreed in 2013 to support initiatives to phase out use of HCFCs. They affirmed the roles of the
4082:
3997:
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3902:
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3652:
3642:
1873:
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1554:
1439:
1318:
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1899:
had developed in the 1930s to generate highly stable perfluorinated materials compatible with
3890:
3702:
3637:
3627:
3289:"Overview on the history of organofluorine chemistry from the viewpoint of material industry"
3122:
3088:
Hope EG, Abbott AP, Davies DL, Solan GA, Stuart AM (2007). "Green
Organometallic Chemistry".
3060:
1877:
1342:
1334:
1074:
402:
207:
1363:
exhibits a high solubility in perfluorocarbon compounds, reflecting on their lipophilicity.
3969:
3954:
3766:
3746:
3494:
3439:
3300:
3261:
3186:
Peters JC, Thomas JC (2007). "Ligands, Reagents, and
Methods in Organometallic Synthesis".
2881:
2777:
2552:
2258:
2106:
1970:
1900:
1849:
1463:
1431:
1270:
926:
756:
728:
181:
151:
2809:"Fluorinated natural products: the biosynthesis of fluoroacetate and 4-fluorothreonine in
2301:
8:
3870:
1959:
1892:
1648:
1607:
has been modified by attachment of perfluoroalkyl substituents that confer solubility in
1534:
1376:
1116:
1070:
727:). Several variations of this technique have been described, including the use of molten
658:
495:
293:
3498:
3443:
3304:
3265:
2978:
2885:
2781:
2556:
2110:
494:
ground state. This difference is significant because difluorocarbene is a precursor to
3520:
3463:
3323:
3288:
2951:
2926:
2907:
2850:
1998:
1936:
1916:
1908:
1885:
1853:
1826:
1604:
1580:. This and related species are useful in organic synthesis and as "shift reagents" in
1538:
1350:
1278:
1274:
816:
812:
394:
198:
3273:
1285:
because of environmental concerns with the ozone layer. HFA propellant inhalers like
3512:
3455:
3328:
3232:
3228:
3199:
3195:
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3162:
3131:
3101:
3097:
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2899:
2842:
2838:
2750:
2726:
2691:
2621:
2589:
2518:
2490:
2457:
Simons JH (1949). "The
Electrochemical Process for the Production of Fluorocarbons".
2436:
2401:
2366:
2212:
2022:
1974:
1822:
1810:
1805:
In contrast to the many naturally-occurring organic compounds containing the heavier
1751:
1596:
1507:
1479:
1475:
1354:
1346:
1282:
1166:
1059:
891:
879:
459:
414:
380:
225:
194:
95:
3357:
2854:
1573:," a coordination complex of europium(III) that features a perfluoroheptyl modified
3524:
3502:
3467:
3447:
3318:
3308:
3269:
3224:
3191:
3158:
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2990:
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2789:
2785:
2718:
2681:
2650:
2613:
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2560:
2466:
2428:
2393:
2358:
2204:
2146:
2114:
2006:
1955:
1951:
1896:
1581:
1537:, can form phases that are insoluble in both water and organic solvents, producing
1423:
1408:
1368:
1364:
925:
convert a variety of oxygen-containing groups into fluorides. The usual reagent is
664:
386:
245:
3595:
3126:
2302:"Climate change: 'Monumental' deal to cut HFCs, fastest growing greenhouse gases"
2138:
2118:
2098:
1947:
1869:
1818:
1608:
1574:
1558:
1483:
1338:
1035:
755:
fluorides are the simplest. For aliphatic compounds this is sometimes called the
471:
444:
437:
270:
135:
127:
111:
3034:
2745:
2617:
2513:
2485:
2259:"The New York Declaration of the Coalition to Secure an Ambitious HFC Amendment"
679:. The method was first demonstrated with the preparation of perfluoropyridine (
3544:
2808:
2384:
Brunet VA, O'Hagan D (2008). "Catalytic asymmetric fluorination comes of age".
2324:"Nations, Fighting Powerful Refrigerant That Warms Planet, Reach Landmark Deal"
1380:
1234:
1190:
1182:
946:
451:
429:
406:
229:
158:
131:
2994:
2825:
Proudfoot AT, Bradberry SM, Vale JA (2006). "Sodium fluoroacetate poisoning".
1915:, provided a host of new reagents starting in the early 1960s. In the 1970s,
4279:
4242:
2942:
2208:
1814:
1813:, a toxin found in a few species of plants. Others include fluorooleic acid,
1530:
1487:
1400:
1310:
1250:
1238:
1206:
1162:
1150:
1125:
760:
491:
479:
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346:
236:
of polyfluorinated compounds whereas other perhalogenated compounds are more
233:
103:
37:
3293:
Proceedings of the Japan
Academy. Series B, Physical and Biological Sciences
3219:
Perutz RN, Braun T (2007). "Transition Metal-mediated C–F Bond Activation".
1173:
is an enzyme capable of biologically synthesizing the carbon–fluorine bond.
413:
emissions are rapidly increasing, causing international concern about their
3516:
3459:
3332:
2960:
2903:
2846:
2730:
2722:
2695:
2440:
2405:
2397:
2370:
2285:
1526:
1451:
1404:
1357:, serve as CFC replacements because they do not catalyze ozone depletion.
1194:
1186:
1063:
1038:
group, for example. Among the available fluorinated building blocks are CF
820:
805:
752:
668:
433:
390:
285:
276:
72:
1565:. Most often, however, fluorocarbon substituents are used to enhance the
663:
A specialized but important method of electrophilic fluorination involves
2686:
2669:
2579:
1392:
1306:
1302:
1258:
1226:
1202:
1198:
887:, a replacement for CFC's, is prepared industrially using this approach:
308:
3313:
2281:"Climate change: global deal reached to limit use of hydrofluorocarbons"
371:). The fluoropolymer polytetrafluoroethylene (PTFE/Teflon) is a solid.
316:
3481:
O'Hagan D, Schaffrath C, Cobb SL, Hamilton JT, Murphy CD (March 2002).
2868:
O'Hagan D, Schaffrath C, Cobb SL, Hamilton JT, Murphy CD (March 2002).
2654:
2170:"100 countries push to phase out potentially disastrous greenhouse gas"
1924:
1833:
1566:
1396:
1388:
1290:
1254:
1246:
1242:
1214:
1158:
632:
602:
289:
237:
122:. In addition to these applications, some organofluorine compounds are
107:
77:
42:
32:
3033:
Ravikumar KS, Kesavan V, Crousse B, Bonnet-Delpon D, Bégué JP (2003).
2670:"PyFluor: A Low-Cost, Stable, and Selective Deoxyfluorination Reagent"
2470:
2432:
2362:
3451:
2150:
1775:
1774:
is a solid acid that is used as the membrane in most low temperature
1384:
1345:
of the carbon-chlorine bonds; their use is largely prohibited by the
1210:
123:
119:
87:
3507:
3482:
3429:
3252:
O'Hagan D, Harper B (1999). "Fluorine-Containing Natural Products".
3032:
2894:
2869:
1329:
Fluorinated compounds often display distinct solubility properties.
2056:
Modern fluoroorganic chemistry: synthesis, reactivity, applications
1544:
1511:
1435:
1230:
1129:
732:
702:
513:
139:
1997:, are persistent global contaminants. Fluorocarbon based CFCs and
1591:
Structure of , a coordination complex of an organofluorine ligand.
1399:. Fluorocarbon anesthetics reduce the hazard of flammability with
1309:
because they concentrate at the liquid-air interface due to their
244:
In comparison to aryl chlorides and bromides, aryl fluorides form
102:. Organofluorine compounds find diverse applications ranging from
3480:
2867:
2198:
2002:
1653:
643:
483:
249:
248:
only reluctantly. On the other hand, aryl fluorides, e.g. fluoro
115:
3537:
2743:
2585:
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
1587:
3597:
1868:
attracted industrial attention in the 1920s. On April 6, 1938,
1830:
1806:
1771:
1763:
1759:
1577:
1557:. One advantage to F-containing ligands is the convenience of
1372:
1360:
911:
676:
517:
425:
253:
2543:
Dolbier Jr WR (2005). "Fluorine Chemistry at the Millennium".
811:
The decomposition of aryldiazonium tetrafluoroborates in the
3152:
2927:"Contribution of Organofluorine Compounds to Pharmaceuticals"
2577:
1825:. Several of these species are probably biosynthesized from
1796:
1570:
1427:
1301:
Fluorosurfactants, which have a polyfluorinated "tail" and a
2588:(6th ed.), New York: Wiley-Interscience, p. 1299,
2349:
Brahms DL, Dailey WP (August 1996). "Fluorinated Carbenes".
2234:"A Sequel to the Paris Climate Accord Takes Shape in Vienna"
1852:
as the F source. The nonflammability and nontoxicity of the
1337:
were at one time widely used refrigerants. CFCs have potent
454:, negotiators from 197 nations meeting at the summit of the
447:, hydrofluorocarbons have other international negotiations.
27:
Study of chemical compounds containing fluorine-carbon bonds
3556:
2261:. Washington, DC: US Department of State. 22 September 2016
1994:
1990:
1943:
1789:
1783:
672:
352:
301:
3483:"Biochemistry: biosynthesis of an organofluorine molecule"
2870:"Biochemistry: biosynthesis of an organofluorine molecule"
2251:
1750:
Organofluorine compounds enjoy many niche applications in
1137:
204:
Fluorine has the lowest polarizability of all atoms: 0.56
1293:) have no generic versions available as of October 2014.
2608:
Wang CJ (1985). "Fluorination by Sulfur Tetrafluoride".
2083:
2418:
1498:
Highly fluorinated substituents, e.g. perfluorohexyl (C
1371:
transporting oxygen to the lungs. Fluorine-substituted
527:
409:. Their atmospheric concentrations and contribution to
256:, often undergo nucleophilic substitution efficiently.
3538:
U.S. White House Press Secretary (September 6, 2013).
2824:
2135:
808:(pyridinium fluoride) or another fluoridating agents.
804:
Alkyl monofluorides can be obtained from alcohols and
3531:
3087:
1979:
United Nations Framework Convention on Climate Change
312:
Segregation of alkyl and perfluoroalkyl substituents.
210:
3058:
2744:
Ramaiah P, Krishnamurti R, Surya Prakash GK (1998).
1930:
1721:
anions. Both tetrakis(pentafluorophenyl)borate, B(C
1717:
Fluorine-containing compounds are often featured in
1220:
259:
3401:
3347:"Dr. Roy J. Plunkett: Discoverer of Fluoropolymers"
2668:Nielsen MK, Ugaz CR, Li W, Doyle AG (August 2015).
2278:
1817:, nucleocidin (4'-fluoro-5'-O-sulfamoyladenosine),
1017:
3120:
2667:
1984:
1549:Organofluorine ligands have long been featured in
759:, while for aromatic compounds it is known as the
216:
3251:
2924:
2383:
2279:Johnston C, Milman O, Vidal J (15 October 2016).
1969:Because of the compound's effect on climate, the
4277:
1545:Organofluorine ligands in coordination chemistry
1269:Fluorocarbons are also used as a propellant for
2483:
1281:inhalers were banned as of 2008 as part of the
2708:
2201:Ullmann's Encyclopedia of Industrial Chemistry
1647:formation with fluorosilane elimination, (iv)
541:, is useful for highly fluorinated compounds:
3581:
2803:
2801:
2799:
2640:
2071:Organic Synthesis: the disconnection approach
1478:. Their strong acidity is attributed to the
620:
36:Some important organofluorine compounds. A:
3185:
2348:
1595:In an area where coordination chemistry and
738:
197:of all elements: 3.98. This causes the high
3218:
2068:
1770:. The polymeric analogue of triflic acid,
1062:that then can be treated with a variety of
652:
501:
145:
3588:
3574:
3221:Comprehensive Organometallic Chemistry III
3188:Comprehensive Organometallic Chemistry III
3155:Comprehensive Organometallic Chemistry III
3090:Comprehensive Organometallic Chemistry III
2796:
2542:
2161:
1445:
3600:with other elements in the periodic table
3506:
3322:
3312:
2972:
2970:
2950:
2893:
2818:
2685:
2452:
2450:
2231:
2194:
2192:
2190:
1919:was established as a useful reagent in F
1569:of metal centers. A premier example is "
1442:is an oxidation-resistant polar solvent.
3009:"Phase-Out of CFC Metered-Dose Inhalers"
2925:Inoue M, Sumii Y, Shibata N (May 2020).
2674:Journal of the American Chemical Society
2049:
2047:
2045:
2043:
2041:
2039:
2037:
1790:Biosynthesis of organofluorine compounds
1586:
436:contain only one fluorine center or one
320:Packing in a crystal pentafluorotolan (C
315:
307:
292:. Because of the reduced intermolecular
31:
2765:
2538:
2536:
2299:
1872:a young research chemist who worked at
1110:
14:
4278:
3617:
3354:The Fluoropolymers Division Newsletter
3286:
2976:
2967:
2459:Journal of the Electrochemical Society
2456:
2447:
2187:
2167:
2073:(2nd ed.). Wiley. pp. 12–13.
2053:
1719:noncoordinating or weakly coordinating
1115:The usefulness of fluorine-containing
3569:
2807:Murphy CD, Schaffrath C, O'Hagan D.:
2571:
2034:
1407:. Perfluorinated alkanes are used as
1264:
443:Unlike other greenhouse gases in the
401:and hydrochlorofluorocarbons such as
374:
4259:Academic research, no widespread use
2607:
2533:
1745:
1379:, including the commercial products
1296:
917:
747:typically of chloride and bromide.
528:Methods for preparation of C–F bonds
456:United Nations Environment Programme
3356:(Summer): 1–2. 1994. Archived from
3280:
2815:Chemosphere. 2003 Jul;52(2):455-61.
2746:"1-trifluoromethyl)-1-cyclohexanol"
1132:by a labeled fluoride nucleophile:
956:A more convenient alternative to SF
177:is relatively short (around 1.4 Ă…).
24:
3157:. Vol. 12. pp. 101–194.
3092:. Vol. 12. pp. 837–864.
1795:
1493:
1144:
642:
126:because of their contributions to
25:
4297:
3223:. Vol. 1. pp. 725–758.
3013:U.S. Food and Drug Administration
2511:
2484:Vogel AI, Leicester J, Macey WA.
1931:Environmental and health concerns
1891:. Electrochemical fluorination ("
1221:Pharmaceuticals and agrochemicals
465:
340:
260:Types of organofluorine compounds
4151:
4070:
4002:
3907:
3607:
2839:10.2165/00139709-200625040-00002
1155:plant defence against herbivores
1136:
1018:From fluorinated building blocks
264:
3474:
3423:
3395:
3367:
3339:
3245:
3212:
3190:. Vol. 1. pp. 59–92.
3179:
3146:
3114:
3081:
3052:
3026:
3001:
2918:
2861:
2759:
2737:
2702:
2661:
2634:
2601:
2505:
2477:
2412:
2377:
2342:
2316:
2293:
1985:Persistence and bioaccumulation
1176:
522:perfluorinated carboxylic acids
355:to partially fluorinated, e.g.
3229:10.1016/B0-08-045047-4/00028-5
3196:10.1016/B0-08-045047-4/00002-9
3163:10.1016/B0-08-045047-4/00169-2
3098:10.1016/B0-08-045047-4/00182-5
3065:Handbook of Fluorous Chemistry
2790:10.1016/j.jfluchem.2006.09.015
2565:10.1016/j.jfluchem.2004.09.033
2272:
2225:
2168:Milman O (22 September 2016).
2129:
2077:
2062:
964:, which is a liquid whereas SF
962:diethylaminosulfur trifluoride
13:
1:
3274:10.1016/S0022-1139(99)00201-8
3254:Journal of Fluorine Chemistry
3121:Crombie A, Kim SY, Hadida S,
2983:Chemical and Engineering News
2769:Journal of Fluorine Chemistry
2545:Journal of Fluorine Chemistry
2300:McGrath M (15 October 2016).
2232:Davenport C (July 23, 2016).
2028:
1762:, made by Solvay Solexis and
1615:. As a specific example, [(C
1034:, is used as a source of the
224:10 cm. This causes very weak
2119:10.1524/zkri.1996.211.12.945
2011:persistent organic pollutant
1921:positron emission tomography
1778:. The bifunctional monomer
1613:supercritical carbon dioxide
1315:perfluorooctanesulfonic acid
1277:-propellant-based inhalers.
1121:positron emission tomography
411:anthropogenic greenhouse gas
7:
3141:, vol. 10, p. 712
3063:, Horváth IT, eds. (2004).
2643:Organic Chemistry Frontiers
2618:10.1002/0471264180.or034.02
2016:
1838:5'-deoxy-5'-fluoroadenosine
1836:catalyzed the synthesis of
1529:, such as organic salts of
1510:. This area, described as "
1490:in substitution reactions.
1367:has been demonstrated as a
1324:
520:, or ionic groups, such as
420:Fluorocarbons with few C-F
365:polychlorotrifluoroethylene
10:
4302:
2977:Thayer AM (June 5, 2006).
2528:, vol. 2, p. 295
2500:, vol. 4, p. 525
2069:Warren S, Wyatt P (2008).
1880:, accidentally discovered
1843:
1171:Adenosyl-fluoride synthase
656:
627:electrophilic fluorination
624:
621:Electrophilic fluorination
505:
378:
344:
294:van der Waals interactions
268:
149:
4234:
4148:
4067:
3619:
3615:
3605:
3409:Science History Institute
3402:Center for Oral History.
3380:Science History Institute
2995:10.1021/cen-v084n023.p015
1876:'s Jackson Laboratory in
1780:4,4'-difluorobenzophenone
1474:H) are useful throughout
1416:1,1,1,2-tetrafluoroethane
1126:fluoride-modified glucose
885:1,1,1,2-Tetrafluoroethane
745:Nucleophilic displacement
739:Nucleophilic fluorination
193:Fluorine has the highest
2943:10.1021/acsomega.0c00830
2209:10.1002/14356007.a11_349
1895:") was announced, which
1525:Hydrophobic fluorinated
653:Electrosynthetic methods
508:Perfluorinated compounds
502:Perfluorinated compounds
146:The carbon–fluorine bond
92:organofluorine compounds
84:Organofluorine chemistry
3067:. Weinheim: Wiley-VCH.
2203:. Weinheim: Wiley-VCH.
1948:deplete the ozone layer
1944:hydrochlorofluorocarbon
1882:polytetrafluoroethylene
1840:(see scheme to right).
1768:liquid crystal displays
1756:coefficient of friction
1739:Ziegler-Natta catalysis
1446:Organofluorine reagents
1331:Dichlorodifluoromethane
1058:I. These species form
357:polyvinylidene fluoride
217:{\displaystyle \times }
170:and chemical stability.
18:Organofluorine compound
4254:Many uses in chemistry
4249:Core organic chemistry
2723:10.1002/chem.201901176
2398:10.1002/anie.200704700
2001:have been reported in
1800:
1592:
1555:coordination chemistry
1440:2,2,2-trifluoroethanol
1319:perfluorooctanoic acid
647:
537:, often diluted with N
393:in place of the older
337:
313:
218:
80:
2827:Toxicological Reviews
2811:Streptomyces cattleya
1878:Deepwater, New Jersey
1799:
1590:
1341:potential due to the
1335:chlorodifluoromethane
1271:metered-dose inhalers
1128:by displacement of a
1075:chlorodifluoromethane
968:is a corrosive gas:
646:
319:
311:
219:
201:of C-F bond (1.41 D).
35:
2687:10.1021/jacs.5b06307
2612:. pp. 319–400.
1971:G-20 major economies
1901:uranium hexafluoride
1850:antimony trifluoride
1464:trifluoroacetic acid
1432:evening primrose oil
1377:volatile anesthetics
1153:, which occurs as a
1117:radiopharmaceuticals
927:sulfur tetrafluoride
757:Finkelstein reaction
751:reactions employing
729:potassium bifluoride
208:
182:Van der Waals radius
175:carbon–fluorine bond
167:carbon–fluorine bond
152:Carbon-fluorine bond
114:, refrigerants, and
100:carbon–fluorine bond
3499:2002Natur.416..279O
3444:1957Natur.179..663H
3314:10.2183/pjab.85.276
3305:2009PJAB...85..276O
3266:1999JFluC.100..127O
2979:"Fabulous Fluorine"
2937:(19): 10633–10640.
2886:2002Natur.416..279O
2782:2006JFluC.127.1488L
2578:Smith, Michael B.,
2557:2005JFluC.126..157D
2111:1996ZK....211..945L
1960:sulfur hexafluoride
1909:noble gas compounds
1893:electrofluorination
1854:chlorofluorocarbons
1649:hydrodefluorination
1539:multiphasic liquids
1535:hexafluorophosphate
1519:fluorous protection
1071:tetrafluoroethylene
817:Schiemann reactions
659:Electrofluorination
601:, analogous to the
496:tetrafluoroethylene
395:chlorofluorocarbons
2655:10.1039/D1QO00952D
2486:"n-Hexyl Fluoride"
1999:tetrafluoromethane
1937:perfluoroisobutene
1917:fluorodeoxyglucose
1827:fluoroacetaldehyde
1801:
1782:is a precursor to
1733:, and the related
1605:triphenylphosphine
1593:
1559:F NMR spectroscopy
1418:has been used for
1351:Hydrofluorocarbons
1343:homolytic cleavage
1265:Inhaler propellant
1111:F-Delivery methods
648:
605:of hydrocarbon in
375:Hydrofluorocarbons
338:
314:
214:
81:
4273:
4272:
4229:
4228:
3557:National Archives
3438:(4561): 663–666.
3404:"Roy J. Plunkett"
3375:"Roy J. Plunkett"
3287:Okazoe T (2009).
3238:978-0-08-045047-6
3205:978-0-08-045047-6
3172:978-0-08-045047-6
3139:Collected Volumes
3132:Organic Syntheses
3107:978-0-08-045047-6
3074:978-3-527-30617-6
3040:Organic Syntheses
2776:(11): 1488–1493.
2751:Organic Syntheses
2717:(30): 7259–7264.
2680:(30): 9571–9574.
2649:(22): 6452–6468.
2627:978-0-471-26418-7
2610:Organic Reactions
2595:978-0-471-72091-1
2526:Collected Volumes
2519:Organic Syntheses
2498:Collected Volumes
2491:Organic Syntheses
2471:10.1149/1.2776733
2433:10.1021/cr040679f
2386:Angewandte Chemie
2363:10.1021/cr941141k
2330:. 15 October 2016
2218:978-3-527-30385-4
2054:Kirsch P (2004).
2023:Hydrofluoroolefin
1975:Montreal Protocol
1786:-class polymers.
1752:materials science
1746:Materials science
1597:materials science
1515:"fluorous tagging
1508:organic synthesis
1480:electronegativity
1476:organic synthesis
1409:blood substitutes
1355:tetrafluoroethane
1347:Montreal Protocol
1305:"head", serve as
1297:Fluorosurfactants
1283:Montreal Protocol
1060:Grignard reagents
923:Deoxofluorination
918:Deoxofluorination
880:hydrogen fluoride
460:Montreal Protocol
415:radiative forcing
381:Hydrofluorocarbon
246:Grignard reagents
226:dispersion forces
195:electronegativity
96:organic compounds
16:(Redirected from
4293:
4265:
4260:
4255:
4250:
4155:
4154:
4074:
4073:
4006:
4005:
3911:
3910:
3608:
3590:
3583:
3576:
3567:
3566:
3561:
3560:
3554:
3553:
3535:
3529:
3528:
3510:
3478:
3472:
3471:
3452:10.1038/179663a0
3427:
3421:
3420:
3418:
3416:
3399:
3393:
3392:
3390:
3388:
3371:
3365:
3364:
3362:
3351:
3343:
3337:
3336:
3326:
3316:
3284:
3278:
3277:
3260:(1–2): 127–133.
3249:
3243:
3242:
3216:
3210:
3209:
3183:
3177:
3176:
3150:
3144:
3142:
3135:
3118:
3112:
3111:
3085:
3079:
3078:
3056:
3050:
3048:
3030:
3024:
3023:
3021:
3019:
3005:
2999:
2998:
2974:
2965:
2964:
2954:
2922:
2916:
2915:
2897:
2865:
2859:
2858:
2822:
2816:
2805:
2794:
2793:
2763:
2757:
2755:
2741:
2735:
2734:
2706:
2700:
2699:
2689:
2665:
2659:
2658:
2638:
2632:
2631:
2605:
2599:
2598:
2575:
2569:
2568:
2540:
2531:
2529:
2522:
2509:
2503:
2501:
2494:
2481:
2475:
2474:
2454:
2445:
2444:
2427:(7): 2943–2989.
2421:Chemical Reviews
2416:
2410:
2409:
2392:(7): 1179–1182.
2381:
2375:
2374:
2357:(5): 1585–1632.
2351:Chemical Reviews
2346:
2340:
2339:
2337:
2335:
2320:
2314:
2313:
2311:
2309:
2297:
2291:
2290:
2276:
2270:
2269:
2267:
2266:
2255:
2249:
2248:
2246:
2244:
2229:
2223:
2222:
2196:
2185:
2184:
2182:
2181:
2165:
2159:
2154:
2151:10.1039/b314094f
2133:
2127:
2122:
2081:
2075:
2074:
2066:
2060:
2059:
2051:
2007:metamorphic rock
1956:perfluorocarbons
1952:greenhouse gases
1927:, was reported.
1897:Joseph H. Simons
1737:, are useful in
1713:
1582:NMR spectroscopy
1424:natural products
1369:blood substitute
1365:Perfluorodecalin
1353:(HFCs), such as
1217:, among others.
1215:water-repellents
1140:
1042:X (X = Br, I), C
1006:
874:
873:
872:
862:
861:
860:
850:
846:
845:
844:
836:
835:
799:
795:
793:
792:
782:
778:
776:
775:
726:
724:
723:
715:
714:
700:
698:
697:
689:
688:
665:electrosynthesis
616:
615:
614:
600:
599:
598:
585:
581:
579:
578:
568:
567:
566:
556:
554:
553:
387:air conditioning
223:
221:
220:
215:
108:water repellents
21:
4301:
4300:
4296:
4295:
4294:
4292:
4291:
4290:
4286:Organofluorides
4276:
4275:
4274:
4269:
4268:
4263:
4258:
4253:
4248:
4230:
4152:
4071:
4003:
3908:
3601:
3594:
3564:
3551:
3549:
3548:(Press release)
3536:
3532:
3508:10.1038/416279a
3479:
3475:
3428:
3424:
3414:
3412:
3400:
3396:
3386:
3384:
3373:
3372:
3368:
3360:
3349:
3345:
3344:
3340:
3285:
3281:
3250:
3246:
3239:
3217:
3213:
3206:
3184:
3180:
3173:
3151:
3147:
3137:
3119:
3115:
3108:
3086:
3082:
3075:
3057:
3053:
3031:
3027:
3017:
3015:
3007:
3006:
3002:
2975:
2968:
2923:
2919:
2895:10.1038/416279a
2866:
2862:
2823:
2819:
2806:
2797:
2764:
2760:
2742:
2738:
2707:
2703:
2666:
2662:
2639:
2635:
2628:
2606:
2602:
2596:
2576:
2572:
2541:
2534:
2524:
2514:"Fluorobenzene"
2510:
2506:
2496:
2482:
2478:
2455:
2448:
2417:
2413:
2382:
2378:
2347:
2343:
2333:
2331:
2322:
2321:
2317:
2307:
2305:
2298:
2294:
2277:
2273:
2264:
2262:
2257:
2256:
2252:
2242:
2240:
2230:
2226:
2219:
2197:
2188:
2179:
2177:
2166:
2162:
2139:J. Mater. Chem.
2134:
2130:
2105:(12): 945–946.
2099:Z. Kristallogr.
2095:
2091:
2087:
2082:
2078:
2067:
2063:
2052:
2035:
2031:
2019:
1987:
1965:
1950:and are potent
1933:
1914:
1889:
1870:Roy J. Plunkett
1867:
1863:
1859:
1846:
1823:2-fluorocitrate
1819:fluorothreonine
1792:
1748:
1732:
1728:
1724:
1712:
1708:
1704:
1700:
1696:
1692:
1688:
1684:
1680:
1676:
1672:
1668:
1664:
1660:
1642:
1638:
1634:
1630:
1626:
1622:
1618:
1609:perfluorohexane
1575:acetylacetonate
1564:
1547:
1505:
1501:
1496:
1494:Fluorous phases
1484:trifluoromethyl
1473:
1469:
1461:
1457:
1448:
1339:ozone depletion
1327:
1299:
1267:
1223:
1183:pharmaceuticals
1179:
1167:2-fluorocitrate
1147:
1145:Biological role
1113:
1103:
1099:
1095:
1088:
1084:
1057:
1053:
1049:
1045:
1041:
1036:trifluoromethyl
1033:
1029:
1025:
1020:
1004:
1000:
996:
992:
988:
984:
980:
976:
972:
967:
959:
950:
944:
940:
936:
920:
905:
901:
895:
871:
868:
867:
866:
864:
859:
856:
855:
854:
852:
848:
843:
840:
839:
838:
834:
831:
830:
829:
827:
800:(M = Na, K, Cs)
797:
791:
788:
787:
786:
784:
780:
774:
771:
770:
769:
767:
741:
722:
719:
718:
717:
713:
710:
709:
708:
706:
696:
693:
692:
691:
687:
684:
683:
682:
680:
661:
655:
636:
629:
623:
613:
610:
609:
608:
606:
597:
594:
593:
592:
590:
583:
577:
574:
573:
572:
570:
565:
562:
561:
560:
558:
552:
549:
548:
547:
545:
540:
536:
530:
510:
504:
489:
477:
472:difluorocarbene
468:
445:Paris Agreement
438:trifluoromethyl
383:
377:
370:
362:
349:
343:
335:
331:
327:
323:
283:
273:
271:Perfluorocarbon
267:
262:
209:
206:
205:
154:
148:
136:bioaccumulation
128:ozone depletion
112:pharmaceuticals
98:that contain a
75:
70:
65:
60:
55:
50:
45:
40:
28:
23:
22:
15:
12:
11:
5:
4299:
4289:
4288:
4271:
4270:
4267:
4266:
4261:
4256:
4251:
4246:
4243:Chemical bonds
4239:
4238:
4236:
4232:
4231:
4227:
4226:
4221:
4216:
4211:
4206:
4201:
4196:
4191:
4186:
4181:
4176:
4171:
4166:
4161:
4156:
4149:
4146:
4145:
4140:
4135:
4130:
4125:
4120:
4115:
4110:
4105:
4100:
4095:
4090:
4085:
4080:
4075:
4068:
4065:
4064:
4060:
4059:
4056:
4053:
4050:
4047:
4044:
4041:
4038:
4035:
4032:
4029:
4026:
4023:
4018:
4015:
4012:
4007:
4000:
3995:
3991:
3990:
3987:
3982:
3977:
3972:
3967:
3962:
3957:
3952:
3947:
3942:
3937:
3932:
3927:
3922:
3917:
3912:
3905:
3900:
3894:
3893:
3888:
3883:
3878:
3873:
3868:
3863:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3811:
3806:
3800:
3799:
3794:
3789:
3784:
3779:
3774:
3769:
3764:
3759:
3754:
3749:
3744:
3739:
3734:
3729:
3724:
3719:
3717:
3712:
3706:
3705:
3700:
3695:
3690:
3685:
3680:
3675:
3670:
3664:
3663:
3660:
3655:
3650:
3645:
3640:
3635:
3630:
3624:
3623:
3620:
3618:
3616:
3614:
3606:
3603:
3602:
3593:
3592:
3585:
3578:
3570:
3563:
3562:
3545:whitehouse.gov
3530:
3473:
3422:
3394:
3366:
3363:on 2003-07-09.
3338:
3299:(8): 276–289.
3279:
3244:
3237:
3211:
3204:
3178:
3171:
3145:
3113:
3106:
3080:
3073:
3051:
3025:
3000:
2966:
2917:
2860:
2833:(4): 213–219.
2817:
2795:
2758:
2736:
2701:
2660:
2633:
2626:
2600:
2594:
2570:
2551:(2): 157–163.
2532:
2504:
2476:
2446:
2411:
2376:
2341:
2328:New York Times
2315:
2292:
2271:
2250:
2224:
2217:
2186:
2160:
2145:(3): 413–420.
2128:
2093:
2089:
2085:
2076:
2061:
2032:
2030:
2027:
2026:
2025:
2018:
2015:
1986:
1983:
1963:
1932:
1929:
1912:
1887:
1865:
1861:
1857:
1845:
1842:
1803:
1802:
1791:
1788:
1754:. With a low
1747:
1744:
1735:tetrakisborate
1730:
1726:
1722:
1715:
1714:
1710:
1706:
1702:
1698:
1694:
1690:
1686:
1682:
1678:
1674:
1670:
1666:
1662:
1640:
1636:
1632:
1628:
1624:
1620:
1616:
1562:
1551:organometallic
1546:
1543:
1503:
1499:
1495:
1492:
1471:
1467:
1459:
1455:
1447:
1444:
1381:methoxyflurane
1326:
1323:
1298:
1295:
1266:
1263:
1235:5-fluorouracil
1222:
1219:
1207:oil-repellents
1191:fluoropolymers
1178:
1175:
1146:
1143:
1142:
1141:
1112:
1109:
1105:
1104:
1101:
1097:
1093:
1090:
1086:
1082:
1055:
1051:
1047:
1043:
1039:
1031:
1027:
1023:
1019:
1016:
1008:
1007:
1002:
998:
994:
990:
986:
982:
978:
974:
965:
957:
954:
953:
948:
942:
938:
934:
919:
916:
908:
907:
903:
899:
893:
876:
875:
869:
857:
841:
832:
823:as F sources.
802:
801:
789:
772:
740:
737:
720:
711:
694:
685:
657:Main article:
654:
651:
650:
649:
634:
622:
619:
611:
595:
587:
586:
575:
563:
550:
538:
534:
529:
526:
506:Main article:
503:
500:
487:
475:
467:
466:Fluorocarbenes
464:
452:climate change
430:5-fluorouracil
407:global warming
379:Main article:
376:
373:
368:
360:
345:Main article:
342:
341:Fluoropolymers
339:
333:
329:
325:
321:
281:
269:Main article:
266:
263:
261:
258:
242:
241:
230:hydrophobicity
213:
202:
191:
178:
171:
159:organohalogens
150:Main article:
147:
144:
132:global warming
86:describes the
26:
9:
6:
4:
3:
2:
4298:
4287:
4284:
4283:
4281:
4262:
4257:
4252:
4247:
4244:
4241:
4240:
4237:
4233:
4225:
4222:
4220:
4217:
4215:
4212:
4210:
4207:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4175:
4172:
4170:
4167:
4165:
4162:
4160:
4157:
4150:
4147:
4144:
4141:
4139:
4136:
4134:
4131:
4129:
4126:
4124:
4121:
4119:
4116:
4114:
4111:
4109:
4106:
4104:
4101:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4079:
4076:
4069:
4066:
4062:
4061:
4057:
4054:
4051:
4048:
4045:
4042:
4039:
4036:
4033:
4030:
4027:
4024:
4022:
4019:
4016:
4013:
4011:
4008:
4001:
3999:
3996:
3993:
3992:
3988:
3986:
3983:
3981:
3978:
3976:
3973:
3971:
3968:
3966:
3963:
3961:
3958:
3956:
3953:
3951:
3948:
3946:
3943:
3941:
3938:
3936:
3933:
3931:
3928:
3926:
3923:
3921:
3918:
3916:
3913:
3906:
3904:
3901:
3899:
3896:
3895:
3892:
3889:
3887:
3884:
3882:
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3862:
3859:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3810:
3807:
3805:
3802:
3801:
3798:
3795:
3793:
3790:
3788:
3785:
3783:
3780:
3778:
3775:
3773:
3770:
3768:
3765:
3763:
3760:
3758:
3755:
3753:
3750:
3748:
3745:
3743:
3740:
3738:
3735:
3733:
3730:
3728:
3725:
3723:
3720:
3718:
3716:
3713:
3711:
3708:
3707:
3704:
3701:
3699:
3696:
3694:
3691:
3689:
3686:
3684:
3681:
3679:
3676:
3674:
3671:
3669:
3666:
3665:
3661:
3659:
3656:
3654:
3651:
3649:
3646:
3644:
3641:
3639:
3636:
3634:
3631:
3629:
3626:
3625:
3621:
3613:
3610:
3609:
3604:
3599:
3596:Compounds of
3591:
3586:
3584:
3579:
3577:
3572:
3571:
3568:
3558:
3547:
3546:
3541:
3534:
3526:
3522:
3518:
3514:
3509:
3504:
3500:
3496:
3493:(6878): 279.
3492:
3488:
3484:
3477:
3469:
3465:
3461:
3457:
3453:
3449:
3445:
3441:
3437:
3433:
3426:
3411:
3410:
3405:
3398:
3382:
3381:
3376:
3370:
3359:
3355:
3348:
3342:
3334:
3330:
3325:
3320:
3315:
3310:
3306:
3302:
3298:
3294:
3290:
3283:
3275:
3271:
3267:
3263:
3259:
3255:
3248:
3240:
3234:
3230:
3226:
3222:
3215:
3207:
3201:
3197:
3193:
3189:
3182:
3174:
3168:
3164:
3160:
3156:
3149:
3140:
3134:
3133:
3128:
3124:
3117:
3109:
3103:
3099:
3095:
3091:
3084:
3076:
3070:
3066:
3062:
3055:
3046:
3042:
3041:
3036:
3029:
3014:
3010:
3004:
2996:
2992:
2989:(23): 15–24.
2988:
2984:
2980:
2973:
2971:
2962:
2958:
2953:
2948:
2944:
2940:
2936:
2932:
2928:
2921:
2913:
2909:
2905:
2901:
2896:
2891:
2887:
2883:
2880:(6878): 279.
2879:
2875:
2871:
2864:
2856:
2852:
2848:
2844:
2840:
2836:
2832:
2828:
2821:
2814:
2812:
2804:
2802:
2800:
2791:
2787:
2783:
2779:
2775:
2771:
2770:
2762:
2753:
2752:
2747:
2740:
2732:
2728:
2724:
2720:
2716:
2712:
2705:
2697:
2693:
2688:
2683:
2679:
2675:
2671:
2664:
2656:
2652:
2648:
2644:
2637:
2629:
2623:
2619:
2615:
2611:
2604:
2597:
2591:
2587:
2586:
2581:
2574:
2566:
2562:
2558:
2554:
2550:
2546:
2539:
2537:
2527:
2521:
2520:
2515:
2508:
2499:
2493:
2492:
2487:
2480:
2472:
2468:
2464:
2460:
2453:
2451:
2442:
2438:
2434:
2430:
2426:
2422:
2415:
2407:
2403:
2399:
2395:
2391:
2387:
2380:
2372:
2368:
2364:
2360:
2356:
2352:
2345:
2329:
2325:
2319:
2303:
2296:
2288:
2287:
2282:
2275:
2260:
2254:
2239:
2235:
2228:
2220:
2214:
2210:
2206:
2202:
2195:
2193:
2191:
2175:
2171:
2164:
2158:entry ASIJIV.
2157:
2152:
2148:
2144:
2141:
2140:
2132:
2126:entry TULQOG.
2125:
2120:
2116:
2112:
2108:
2104:
2101:
2100:
2080:
2072:
2065:
2057:
2050:
2048:
2046:
2044:
2042:
2040:
2038:
2033:
2024:
2021:
2020:
2014:
2012:
2008:
2004:
2000:
1996:
1992:
1982:
1980:
1976:
1972:
1967:
1961:
1957:
1953:
1949:
1945:
1940:
1938:
1928:
1926:
1922:
1918:
1910:
1904:
1902:
1898:
1894:
1890:
1883:
1879:
1875:
1871:
1855:
1851:
1841:
1839:
1835:
1832:
1828:
1824:
1820:
1816:
1815:fluoroacetone
1812:
1811:fluoroacetate
1808:
1798:
1794:
1793:
1787:
1785:
1781:
1777:
1773:
1769:
1765:
1761:
1757:
1753:
1743:
1740:
1736:
1720:
1659:
1658:
1657:
1655:
1650:
1644:
1614:
1610:
1606:
1601:
1598:
1589:
1585:
1583:
1579:
1576:
1572:
1568:
1567:Lewis acidity
1560:
1556:
1552:
1542:
1540:
1536:
1532:
1531:bistriflimide
1528:
1527:ionic liquids
1523:
1522:
1518:
1513:
1509:
1491:
1489:
1488:leaving group
1485:
1481:
1477:
1465:
1453:
1443:
1441:
1437:
1433:
1429:
1425:
1421:
1417:
1412:
1410:
1406:
1402:
1401:diethyl ether
1398:
1394:
1390:
1386:
1382:
1378:
1374:
1370:
1366:
1362:
1358:
1356:
1352:
1348:
1344:
1340:
1336:
1332:
1322:
1320:
1316:
1312:
1311:lipophobicity
1308:
1304:
1294:
1292:
1289:and ProAir (
1288:
1284:
1280:
1276:
1272:
1262:
1260:
1256:
1252:
1251:ciprofloxacin
1248:
1244:
1240:
1239:flunitrazepam
1236:
1232:
1228:
1218:
1216:
1212:
1208:
1204:
1200:
1196:
1192:
1188:
1187:agrichemicals
1184:
1174:
1172:
1168:
1164:
1163:fluoroacetone
1160:
1156:
1152:
1151:fluoroacetate
1139:
1135:
1134:
1133:
1131:
1127:
1122:
1118:
1108:
1091:
1080:
1079:
1078:
1076:
1072:
1067:
1065:
1064:electrophiles
1061:
1037:
1015:
1013:
971:
970:
969:
963:
951:
932:
931:
930:
928:
924:
915:
913:
897:
890:
889:
888:
886:
881:
826:
825:
824:
822:
821:fluoroborates
818:
814:
809:
807:
766:
765:
764:
762:
761:Halex process
758:
754:
750:
746:
736:
734:
730:
704:
678:
674:
670:
666:
660:
645:
641:
640:
639:
637:
628:
618:
604:
544:
543:
542:
525:
523:
519:
515:
509:
499:
497:
493:
485:
481:
478:, which is a
473:
463:
461:
457:
453:
448:
446:
441:
439:
435:
434:agrochemicals
431:
427:
423:
418:
416:
412:
408:
404:
400:
396:
392:
388:
382:
372:
366:
358:
354:
348:
347:Fluoropolymer
318:
310:
306:
303:
297:
295:
291:
287:
286:Fluorocarbons
278:
277:fluorocarbons
272:
265:Fluorocarbons
257:
255:
251:
247:
239:
235:
234:lipophobicity
231:
227:
211:
203:
200:
199:dipole moment
196:
192:
188:
187:steric strain
183:
179:
176:
172:
168:
164:
163:
162:
160:
153:
143:
141:
137:
133:
129:
125:
121:
117:
113:
109:
105:
101:
97:
93:
89:
85:
79:
74:
69:
64:
59:
54:
49:
44:
39:
38:fluoromethane
34:
30:
19:
4264:Bond unknown
3657:
3555:– via
3550:. Retrieved
3543:
3533:
3490:
3486:
3476:
3435:
3431:
3425:
3413:. Retrieved
3407:
3397:
3385:. Retrieved
3378:
3369:
3358:the original
3353:
3341:
3296:
3292:
3282:
3257:
3253:
3247:
3220:
3214:
3187:
3181:
3154:
3148:
3138:
3130:
3116:
3089:
3083:
3064:
3059:Gladysz JA,
3054:
3044:
3038:
3028:
3018:10 September
3016:. Retrieved
3012:
3003:
2986:
2982:
2934:
2930:
2920:
2877:
2873:
2863:
2830:
2826:
2820:
2810:
2773:
2767:
2761:
2749:
2739:
2714:
2710:
2704:
2677:
2673:
2663:
2646:
2642:
2636:
2609:
2603:
2584:
2580:March, Jerry
2573:
2548:
2544:
2525:
2517:
2507:
2497:
2489:
2479:
2465:(2): 47–66.
2462:
2458:
2424:
2420:
2414:
2389:
2385:
2379:
2354:
2350:
2344:
2332:. Retrieved
2327:
2318:
2306:. Retrieved
2295:
2286:The Guardian
2284:
2274:
2263:. Retrieved
2253:
2241:. Retrieved
2237:
2227:
2200:
2178:. Retrieved
2176:. London, UK
2174:The Guardian
2173:
2163:
2142:
2137:
2131:
2102:
2097:
2079:
2070:
2064:
2058:. Wiley-VCH.
2055:
2009:. PFOS is a
1988:
1968:
1958:(PFCs), and
1941:
1934:
1905:
1847:
1804:
1749:
1716:
1705:ZrH(F) + C
1645:
1602:
1594:
1548:
1524:
1520:
1516:
1497:
1452:Triflic acid
1449:
1414:The solvent
1413:
1405:cyclopropane
1359:
1328:
1300:
1268:
1241:(Rohypnol),
1224:
1195:refrigerants
1180:
1177:Applications
1148:
1114:
1106:
1068:
1021:
1011:
1009:
955:
921:
909:
877:
810:
806:Olah reagent
803:
753:alkali metal
742:
669:electrolyzed
662:
630:
588:
531:
511:
469:
449:
442:
419:
391:refrigerants
384:
350:
298:
274:
243:
155:
91:
83:
82:
73:fluorouracil
58:triflic acid
29:
3415:21 February
3387:21 February
3383:. June 2016
1611:as well as
1393:sevoflurane
1317:(PFOS) and
1307:surfactants
1303:hydrophilic
1259:fluconazole
1227:bioisostere
1203:anesthetics
1199:surfactants
1159:fatty acids
731:or organic
3552:2013-09-16
2512:Flood DT.
2334:15 October
2308:15 October
2304:. BBC News
2265:2016-09-22
2180:2016-09-22
2029:References
1925:fluorinase
1911:, e.g. XeF
1834:fluorinase
1776:fuel cells
1420:extraction
1397:desflurane
1389:isoflurane
1291:Salbutamol
1255:mefloquine
1247:paroxetine
1245:(Prozac),
1243:fluoxetine
898:+ 4 HF → F
749:Metathesis
625:See also:
603:combustion
290:lipophobic
275:Formally,
252:and fluoro
238:lipophilic
190:compounds.
124:pollutants
78:fluoxetine
43:isoflurane
4245:to carbon
3123:Curran DP
3061:Curran DP
2931:ACS Omega
2711:Chemistry
2243:17 August
1860:F and CCl
1385:enflurane
1253:(Cipro),
1249:(Paxil),
1211:catalysis
1050:Br, and C
981:CHO + R
878:Although
813:Sandmeyer
675:using Ni
633:F-TEDA-BF
212:×
120:catalysis
88:chemistry
4280:Category
3517:11907567
3460:13418758
3333:19838009
2961:32455181
2904:11907567
2855:29189551
2847:17288493
2731:30869818
2696:26177230
2582:(2007),
2441:16836305
2406:18161722
2371:11848805
2017:See also
1977:and the
1512:fluorous
1436:vanillin
1426:such as
1325:Solvents
1231:hydrogen
1130:triflate
819:exploit
733:solvents
703:pyridine
514:nitrogen
490:) has a
482:whereas
397:such as
250:anilines
140:toxicity
116:reagents
4063:
3525:4415511
3495:Bibcode
3468:4296069
3440:Bibcode
3324:3621566
3301:Bibcode
3262:Bibcode
2952:7240833
2912:4415511
2882:Bibcode
2778:Bibcode
2553:Bibcode
2107:Bibcode
2003:igneous
1844:History
1807:halides
1654:hydride
1482:of the
1462:H) and
1287:FloVent
1229:of the
960:is the
906:+ 3 HCl
701:) from
671:at 5–6
492:triplet
484:carbene
480:singlet
440:group.
389:and as
254:phenols
4235:Legend
3598:carbon
3523:
3515:
3487:Nature
3466:
3458:
3432:Nature
3331:
3321:
3235:
3202:
3169:
3104:
3071:
2959:
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2874:Nature
2853:
2845:
2729:
2694:
2624:
2592:
2439:
2404:
2369:
2215:
1874:DuPont
1831:enzyme
1829:. The
1821:, and
1772:nafion
1764:DuPont
1760:Krytox
1578:ligand
1434:, and
1373:ethers
1361:Oxygen
1257:, and
1213:, and
1165:, and
1089:+ HCl
1085:→ CF
937:H + SF
912:alkene
896:C=CClH
677:anodes
518:iodine
426:uracil
363:) and
138:, and
63:Teflon
53:an HFC
3521:S2CID
3464:S2CID
3361:(PDF)
3350:(PDF)
3047:: 184
2908:S2CID
2851:S2CID
2754:: 232
1689:→ (C
1681:+ FC
1571:Eufod
1428:taxol
1119:in F-
1096:→ C
1081:CHClF
1026:Si(CH
1005:NSOF"
1001:+ "R
989:→ C
941:→ RCF
422:bonds
48:a CFC
3513:PMID
3456:PMID
3417:2018
3389:2018
3329:PMID
3233:ISBN
3200:ISBN
3167:ISBN
3102:ISBN
3069:ISBN
3020:2017
2957:PMID
2900:PMID
2843:PMID
2727:PMID
2692:PMID
2622:ISBN
2590:ISBN
2437:PMID
2402:PMID
2367:PMID
2336:2016
2310:2016
2245:2016
2213:ISBN
2096:O".
2005:and
1995:PFOA
1993:and
1991:PFOS
1784:PEEK
1631:-4-C
1553:and
1517:and
1403:and
1395:and
1375:are
1333:and
1092:2 CF
952:+ HF
902:CCFH
474:, CF
428:and
403:R-21
399:R-12
353:PTFE
302:PFOA
232:and
180:The
173:The
165:The
106:and
68:PFOS
4209:CEs
4204:CCf
4199:CBk
4194:CCm
4189:CAm
4184:CPu
4179:CNp
4169:CPa
4164:CTh
4143:CYb
4138:CTm
4133:CEr
4128:CHo
4123:CDy
4118:CTb
4113:CGd
4108:CEu
4103:CSm
4098:CPm
4093:CNd
4088:CPr
4083:CCe
4078:CLa
4058:Og
4055:Ts
4052:Lv
4049:Mc
4046:Fl
4043:Nh
4040:Cn
4037:Rg
4034:Ds
4031:Mt
4028:Hs
4025:Bh
4021:CSg
4017:Db
4014:Rf
3998:CRa
3994:Fr
3989:Rn
3985:CAt
3980:CPo
3975:CBi
3970:CPb
3965:CTl
3960:CHg
3955:CAu
3950:CPt
3945:CIr
3940:COs
3935:CRe
3925:CTa
3920:CHf
3915:CLu
3903:CBa
3898:CCs
3891:CXe
3881:CTe
3876:CSb
3871:CSn
3866:CIn
3861:CCd
3856:CAg
3851:CPd
3846:CRh
3841:CRu
3836:CTc
3831:CMo
3826:CNb
3821:CZr
3809:CSr
3804:CRb
3797:CKr
3792:CBr
3787:CSe
3782:CAs
3777:CGe
3772:CGa
3767:CZn
3762:CCu
3757:CNi
3752:CCo
3747:CFe
3742:CMn
3737:CCr
3727:CTi
3722:CSc
3715:CCa
3703:CAr
3698:CCl
3683:CSi
3678:CAl
3673:CMg
3668:CNa
3662:Ne
3633:CBe
3628:CLi
3622:He
3503:doi
3491:416
3448:doi
3436:179
3319:PMC
3309:doi
3270:doi
3258:100
3225:doi
3192:doi
3159:doi
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2991:doi
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2939:doi
2890:doi
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2786:doi
2774:127
2719:doi
2682:doi
2678:137
2651:doi
2614:doi
2561:doi
2549:126
2467:doi
2429:doi
2425:106
2394:doi
2359:doi
2238:NYT
2205:doi
2156:CSD
2147:doi
2124:CSD
2115:doi
2103:211
1966:).
1962:(SF
1886:CoF
1856:CCl
1693:(CH
1677:ZrH
1665:(CH
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1533:or
1466:(CF
1454:(CF
1438:.
1422:of
1279:CFC
1275:CFC
997:CHF
985:NSF
933:RCO
929::
849:ArF
828:ArN
815:or
798:MCl
777:CCl
486:(CH
328:CCC
280:(CF
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