583:
723:
62:
83:
304:
229:
47:
582:
578:
690:
584:
581:
842:-BuLi exists as a cluster both in the solid state and in a solution. The tendency to aggregate is common for organolithium compounds. The aggregates are held together by delocalized covalent bonds between lithium and the terminal carbon of the butyl chain. In the case of
1988:
Juaristi, E.; MartĂnez-Richa, A.; GarcĂa-Rivera, A.; Cruz-SĂĄnchez, J. S. (1983). "Use of 4-Biphenylmethanol, 4-Biphenylacetic Acid and 4-Biphenylcarboxylic Acid/Triphenylmethane as
Indicators in the Titration of Lithium Alkyls. Study of the Dianion of 4-Biphenylmethanol".
1505:
These side reaction are significantly less important for RI than for RBr, since the iodineâlithium exchange is several orders of magnitude faster than the bromineâlithium exchange. For these reasons, aryl, vinyl and primary alkyl iodides are the preferred substrates, and
606:
599:
1404:
Butyllithium reacts with some organic bromides and iodides in an exchange reaction to form the corresponding organolithium derivative. The reaction usually fails with organic chlorides and fluorides:
821:-butyllithium is usually encountered as a pale yellow solution in alkanes. Such solutions are stable indefinitely if properly stored, but in practice, they degrade upon aging. Fine white precipitate (
968:, cyclohexane, and diethyl ether. When BuBr is the precursor, the product is a homogeneous solution, consisting of a mixed cluster containing both LiBr and BuLi, together with a small amount of
814:
can be prepared, but are not stable enough for storage. Annual worldwide production and consumption of butyllithium and other organolithium compounds is estimated at 2000 to 3000 tonnes.
2327:
1529:-BuLi). Alternatively, vinyl lithium reagents can be generated by direct reaction of the vinyl halide (e.g. cyclohexenyl chloride) with lithium or by tinâlithium exchange (see next section).
2535:
1275:) further polarize the LiâC bond and accelerate the metalation. Such additives can also aid in the isolation of the lithiated product, a famous example of which is dilithioferrocene.
3159:
3728:
2379:
2354:
1882:
Schwindeman, James A. (1 August 2014). "Preparation, Properties, and Safe
Handling of Commercial Organolithiums: Alkyllithiums, Lithium sec-Organoamides, and Lithium Alkoxides".
1581:
The tinâlithium exchange reactions have one major advantage over the halogenâlithium exchanges for the preparation of organolithium reagents, in that the product tin compounds (C
2905:
3790:
3251:
3012:
3000:
2979:
3743:
3710:
3287:
2839:
2385:
2571:
3080:
3692:
3503:
3032:
873:. Bonding within the cluster is related to that used to describe diborane, but more complex since eight atoms are involved. Reflecting its electron-rich character,
2896:
3060:
3048:
2676:
2644:
3498:
3439:
3427:
2558:
4624:
3415:
3403:
3315:
3266:
2660:
2582:
1678:, by loss of one of four protons adjacent to oxygen. This process, which consumes butyllithium to generate butane, induces a ring opening to give enolate of
3098:
2858:
2603:
3808:
3668:
3391:
3072:
2967:
2724:
2033:
Delaney, M. S. (20 January 1991). "The rate of ethylene polymerization initiated by various chelating tertiary diamine : nâbutyllithium complexes".
1219:
carbonyl compounds, and any overtly acidic compounds, to produce alkoxides, amides, enolates and other salts of lithium, respectively. The stability and
4349:
3562:
3550:
2827:
2795:
2706:
2374:
2362:
703:
4339:
3574:
3340:
2736:
2689:
2595:
2587:
2015:
Ulrich
Wietelmann and Richard J. Bauer "Lithium and Lithium Compounds" in Ullmann's Encyclopedia of Industrial Chemistry, 2002, Wiley-VCH, Weinheim.
1593:
in the example above) are much less reactive towards lithium reagents than are the halide products of the corresponding halogenâlithium exchanges (C
4329:
3282:
3103:
4319:
2187:
1686:. Therefore, reactions of BuLi in THF are typically conducted at low temperatures, such as â78 °C, as is conveniently produced by a
4642:
4460:
4426:
4334:
4324:
4531:
4361:
353:
4555:
2234:
4480:
3884:
2401:
2060:
Sanders, R.; Mueller-Westerhoff, U. T. (1996). "The
Lithiation of Ferrocene and Ruthenocene â A Retraction and an Improvement".
4778:
4629:
3783:
1050:
can be polymerized stereospecifically in this way. Also of commercial importance is the use of butyllithium for the production of
4804:
4634:
1231:
reactions is convenient, but can also be a problem for large-scale reactions because of the volume of a flammable gas produced.
4727:
4701:
4681:
2283:
2179:
1541:, wherein two organometallic compounds exchange their metals. Many examples of such reactions involve lithium exchange with
896:(0.98), the CâLi bond is highly polarized. The charge separation has been estimated to be 55â95%. For practical purposes,
2162:
1444:
lithium reagents. The utility of this method is significantly limited, however, by the presence in the reaction mixture of
698:
2062:
613:
1975:
1929:
318:
592:
4799:
3906:
3825:
3185:
710:
2227:
4604:
964:, the reaction proceeds more quickly than if pure lithium is used. Solvents used for this preparation include
540:
17:
4819:
4246:
1852:
2256:
3536:
2774:
2273:
1433:
261:
224:
4768:
1785:
This is an exergonic and highly exothermic reaction. If oxygen is present the butane produced may ignite.
1750:
Alkyl-lithium compounds are stored under inert gas to prevent loss of activity and for reasons of safety.
4676:
4221:
3383:
2955:
2947:
2914:
2521:
2417:
972:. BuLi forms a weaker complex with LiCl, so that the reaction of BuCl with Li produces a precipitate of
282:
2167:
3994:
3579:
3299:
2507:
2493:
2483:
2220:
1264:
1215:)). In addition to these, it will also deprotonate all more acidic compounds such as alcohols, amines,
484:
4306:
3975:
3942:
2427:
2309:
4814:
3957:
3775:
1707:
1622:
1089:, which partially disaggregate the clusters by binding to the lithium centers. Its use as a strong
299:
2121:
1987:
2090:
1334:
1268:
3327:
2932:
2874:
1220:
166:
1341:. It is kinetically more reactive than butyllithium and is often used to accomplish difficult
206:
4232:
3843:
3591:
1114:
834:
752:
634:
99:
1649:. One such synthetic pathway is the reaction of an organolithium reagent with disubstituted
1081:, depending on the other reactants. Furthermore, in addition to being a strong nucleophile,
979:
Solutions of butyllithium, which are susceptible to degradation by air, are standardized by
722:
82:
61:
4696:
3648:
3603:
2819:
2790:
2785:
862:
R groups at alternating vertices. An equivalent description describes the tetramer as a Li
270:
2091:"The "super-basic" butyllithium/potassium tert-butoxide mixture and other lickor-reagents"
8:
4809:
4101:
3493:
3024:
2811:
2435:
1453:
1364:-butyllithium as a base is the addition of an amine to methyl carbonate to form a methyl
1326:
851:
142:
132:
1946:
1139:-BuLi can deprotonate (that is, metalate) many types of CâH bonds, especially where the
303:
228:
186:
4354:
3615:
3332:
2443:
2251:
508:
2106:
4612:
4203:
4060:
3866:
3763:
3656:
3639:
3631:
3472:
3460:
3374:
3369:
3173:
3119:
2886:
2741:
2697:
2453:
2319:
2243:
2141:
2075:
1971:
1925:
1779:
1507:
1051:
885:
780:
768:
672:
649:
557:
4758:
4465:
4181:
4115:
4042:
3680:
3541:
3451:
3357:
2891:
2803:
2769:
2623:
2349:
2196:
2133:
2102:
2071:
2042:
2016:
1998:
1891:
1694:
and acetone. Higher temperatures (â25 °C or even â15 °C) are also used.
1436:
reaction is useful for preparation of several types of RLi compounds, particularly
1105:, which are good solvents for the resulting organolithium derivatives (see below).
1090:
973:
772:
642:
459:
376:
46:
1124:
250:
4446:
4276:
4167:
4130:
3920:
3855:
3524:
3512:
3484:
3307:
3243:
3235:
3209:
3127:
2995:
2753:
2719:
2635:
2611:
2566:
1921:
1830:
1715:
1538:
1260:
1098:
822:
520:
476:
1706:-BuLi, analogously to other alkyllithium reagents with "β-hydrogens", undergoes
987:-4-methanol, which gives a deeply colored dilithio derivative at the end point.
4763:
3848:
3111:
3093:
3088:
2467:
2046:
1259:-BuLi is affected by the solvent or cosolvent. Ligands that complex Li such as
1144:
1140:
996:
929:
756:
681:
4793:
4436:
4386:
4152:
4090:
3348:
3226:
3218:
3201:
2200:
2145:
2020:
1687:
1618:
1228:
1102:
925:
807:
764:
660:
448:
438:
217:
1147:
or one or more heteroatoms (non-carbon atoms). Examples include acetylenes (
4753:
4691:
4261:
4075:
4012:
3829:
1525:-BuLi in a dehydrohalogenation reaction (thus requiring two equivalents of
656:
605:
4594:
4499:
4314:
1441:
1353:-BuLi, the reactivity of the mixture is not exactly the same as isolated
1074:
866:
847:
612:
2002:
786:
Butyllithium is commercially available as solutions (15%, 25%, 1.5
591:
4589:
4575:
4565:
4560:
4521:
4431:
4376:
4366:
3838:
2122:"Pathways for decomposition of THF by organolithiums: the role of HMPA"
1342:
1094:
878:
598:
470:
401:
197:
2176:, July 1998, p681.7002, Chemicals Economics Handbook SRI International
1895:
4686:
4536:
4526:
4475:
4470:
4381:
2265:
2137:
1626:
1614:
1365:
1330:
1192:
1188:
1078:
1004:
980:
776:
760:
337:
InChI=1/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;/rC4H9Li/c1-2-3-4-5/h2-4H2,1H3
2212:
2059:
1452:-BuI, which can react with the RLi reagent formed, and by competing
680:
Except where otherwise noted, data are given for materials in their
4550:
4485:
4391:
1711:
1674:
THF is deprotonated by butyllithium, especially in the presence of
1642:
1168:
1055:
1047:
995:
Butyllithium is principally valued as an initiator for the anionic
984:
787:
564:
1860:
165:
4773:
4421:
4406:
4344:
1691:
1679:
965:
893:
803:
795:
428:
237:
1970:
Elschenbroich, C. âOrganometallicsâ (2006) Wiley-VCH: Weinheim.
1085:-BuLi binds to aprotic Lewis bases, such as ethers and tertiary
2942:
1683:
1646:
1617:
which undergo such exchange reactions are organic compounds of
1224:
969:
961:
909:
889:
846:-BuLi, the clusters are tetrameric (in ether) or hexameric (in
799:
791:
1915:
2927:
1675:
1650:
1610:
1272:
1184:
1086:
1000:
901:
527:
177:
155:
287:
3139:
1437:
1216:
88:
Close-up of the delocalized bonds between butyl and lithium
2120:
Clayden, Jonathan; Yasin, Samreen A. (11 February 2002).
1542:
1123:-BuLi is its ability to deprotonate a wide range of weak
811:
1349:-butylpotassium is present and is a stronger base than
960:
If the lithium used for this reaction contains 1â3%
900:-BuLi can often be considered to react as the butyl
443:â76 °C (â105 °F; 197 K) (<273 K)
2089:Schlosser, Manfred; Strunk, Sven (January 1984).
4791:
825:) is deposited and the color changes to orange.
249:
3839:Hemolithin (extraterrestrial protein)
2088:
1372:-butyllithium serves to deprotonate the amine:
580:
141:
2209:, 2nd ed. 1997: Butterworth-Heinemann, Boston.
2188:Encyclopedia of Reagents for Organic Synthesis
2180:HPV test plan, submitted by FMC Lithium to EPA
1119:One of the most useful chemical properties of
2228:
1073: â -36), but it is also a powerful
1007:. The reaction is called "carbolithiation":
2119:
1918:Preparative Polar Organometallic Chemistry I
790:, 2 M, 2.5 M, 10 M, etc.) in
1881:
1399:
771:. Also, it is broadly employed as a strong
554:Pyrophoric (spontaneously combusts in air),
2235:
2221:
1911:
1909:
1907:
1905:
1884:Organic Process Research & Development
302:
227:
205:
2163:FMC Lithium manufacturer's product sheets
1916:Brandsma, L.; Verkruijsse, H. D. (1987).
269:
4779:Environmentally friendly red light flare
1697:
1641:-BuLi are used in synthesis of specific
1517:-BuLi is usually used, since the formed
1097:. Reactions are typically conducted in
884:Due to the large difference between the
877:-butyllithium is highly reactive toward
828:
721:
327:InChI=1S/C4H9.Li/c1-3-4-2;/h1,3-4H2,2H3;
2032:
1902:
1333:produced by treating butyllithium with
298:
14:
4792:
4682:Heteroatom-promoted lateral lithiation
2195:-Butyllithium." Wiley and sons. 2006.
1537:A related family of reactions are the
218:
2242:
2216:
1669:
1632:
1521:-BuI is immediately destroyed by the
726:Glass bottles containing butyllithium
330:Key: MZRVEZGGRBJDDB-UHFFFAOYSA-N
185:
1271:(HMPA), and 1,4-diazabicyclooctane (
817:Although butyllithium is colorless,
2172:Weissenbacher, Anderson, Ishikawa,
2063:Journal of Organometallic Chemistry
1850:
1754:-BuLi reacts violently with water:
1577:(where Ar is aryl and Me is methyl)
1532:
869:interpenetrated with a tetrahedron
783:as in the pharmaceutical industry.
340:Key: MZRVEZGGRBJDDB-NESCHKHYAE
240:
24:
2156:
2035:Journal of Applied Polymer Science
1637:Organolithium reagents, including
576:
60:
45:
25:
4831:
2168:Environmental Chemistry directory
1991:The Journal of Organic Chemistry
1066:Butyllithium is a strong base (p
688:
388:
81:
2205:Greenwood, N. N.; Earnshaw, A.
2113:
2082:
990:
769:styrene-butadiene-styrene (SBS)
759:initiator in the production of
684:(at 25 °C , 100 kPa).
394:
4805:Reagents for organic chemistry
2053:
2026:
2009:
1981:
1964:
1939:
1875:
1844:
1135:-butyllithium are more basic.
915:
850:). The cluster is a distorted
781:synthesis of organic compounds
541:Occupational safety and health
382:
13:
1:
4769:Magnesiumâlithium alloys
2107:10.1016/S0040-4039(01)80014-9
1837:
1833:, an organometallic compound.
1108:
920:The standard preparation for
2076:10.1016/0022-328X(95)05914-B
1792:to give lithium pentanoate:
1061:
7:
4438:Lithiophilite LiMnPO
1824:
1143:is stabilized by electron
497:50 (of the conjugate acid)
433:0.68 g/cm, solvent defined
41:
10:
4836:
2047:10.1002/app.1991.070420226
1265:tetramethylethylenediamine
1112:
983:. A popular weak acid is
832:
4669:
4603:
4538:Spodumene LiAl(SiO
4448:Lithiophosphate Li
4368:Eucryptite LiAlSiO
4305:
3824:
2250:
2207:Chemistry of the Elements
1947:"n-Butyllithium solution"
1745:
1360:An example of the use of
755:. It is widely used as a
678:
626:
538:
533:
501:
465:Exothermic decomposition
369:
349:
314:
125:
115:
98:
93:
80:
40:
4677:Aluminiumâlithium alloys
4567:Triphylite LiFePO
4501:Pezzottaite Cs(Be
2201:10.1002/047084289X.rb395
2126:New Journal of Chemistry
2021:10.1002/14356007.a15_393
1853:"Some useful pKa values"
1788:BuLi also reacts with CO
1460:-BuLi serves as a base:
1434:lithiumâhalogen exchange
1400:Halogenâlithium exchange
1255:The kinetic basicity of
1151:CCâR), methyl sulfides (
556:decomposes to corrosive
4800:Organolithium compounds
4393:Jadarite LiNaSiB
1269:hexamethylphosphoramide
1058:will insert into BuLi.
514:tetrameric in solution
4487:Petalite LiAlSi
4408:Keatite Li(AlSi
3844:Organolithium reagents
1171:), methylphosphines (
727:
587:
65:
56:-Butyllithium tetramer
50:
1708:β-hydride elimination
1698:Thermal decomposition
1115:Organolithium reagent
924:-BuLi is reaction of
835:Organolithium reagent
829:Structure and bonding
753:organolithium reagent
725:
586:
71:-Butyllithium hexamer
64:
49:
4820:Pyrophoric materials
4577:Zabuyelite Li
1493:Li + Râ˛CH=CHBr â 2 C
1456:reactions, in which
1227:resulting from such
569:(fire diamond)
103:butyllithium, tetra-
2095:Tetrahedron Letters
2003:10.1021/jo00163a038
1454:dehydrohalogenation
908:-Bu, and a lithium
886:electronegativities
852:cubane-type cluster
460:Solubility in water
409: g¡mol
110:-butyl-tetralithium
37:
4697:Lithium medication
4355:Fluor-liddicoatite
4271: Vinyllithium
1670:Degradation of THF
1633:Carbonyl additions
1159:SR), thioacetals (
1131:-Butyllithium and
1093:is referred to as
728:
711:Infobox references
627:Related compounds
588:
66:
51:
32:
4787:
4786:
2244:Lithium compounds
1997:(15): 2603â2606.
1896:10.1021/op500161b
1890:(10): 1192â1210.
1440:lithium and some
1357:-butylpotassium.
1052:styrene-butadiene
719:Chemical compound
717:
716:
673:lithium hydroxide
668:Related compounds
283:CompTox Dashboard
167:Interactive image
76:
75:
27:Chemical compound
16:(Redirected from
4827:
4759:Lithium Triangle
4670:Other Li-related
4585:
4571:
4546:
4517:
4495:
4466:Manganoneptunite
4456:
4442:
4417:
4402:
4372:
4350:Fluorine Elbaite
4297:
4295:
4294:
4286:
4285:
4272:
4257:
4242:
4228:
4217:
4199:
4177:
4163:
4148:
4126:
4111:
4097:
4086:
4071:
4056:
4038:
4023:
4008:
3990:
3971:
3953:
3938:
3916:
3902:
3880:
3862:
3804:
3739:
3724:
3706:
3262:
3169:
2938:
2854:
2781:
2578:
2554:
2531:
2517:
2503:
2489:
2463:
2449:
2423:
2345:
2315:
2305:
2279:
2259:
2237:
2230:
2223:
2214:
2213:
2150:
2149:
2138:10.1039/B109604D
2117:
2111:
2110:
2086:
2080:
2079:
2070:(1â2): 219â224.
2057:
2051:
2050:
2030:
2024:
2013:
2007:
2006:
1985:
1979:
1968:
1962:
1961:
1959:
1957:
1951:sigmaaldrich.com
1943:
1937:
1935:
1913:
1900:
1899:
1879:
1873:
1872:
1870:
1868:
1859:. Archived from
1851:Bernier, David.
1848:
1576:
1539:transmetalations
1533:Transmetalations
1501:+ Râ˛CâĄCLi + LiBr
1427:
1395:Me + LiOMe + BuH
1327:Schlosser's base
1054:polymers. Even
955:
806:. Solutions in
744:Li (abbreviated
701:
695:
692:
691:
617:
616:
608:
601:
594:
579:
421:usually obtained
417:colorless liquid
408:
396:
390:
384:
377:Chemical formula
307:
306:
291:
289:
273:
253:
242:
231:
220:
209:
189:
169:
145:
85:
42:
38:
31:
21:
4835:
4834:
4830:
4829:
4828:
4826:
4825:
4824:
4815:Butyl compounds
4790:
4789:
4788:
4783:
4749:
4745:
4739:
4733:
4723:
4719:
4713:
4707:
4665:
4661:
4657:
4653:
4646:
4638:
4620:
4616:
4599:
4584:
4580:
4576:
4570:
4566:
4545:
4541:
4537:
4516:
4512:
4508:
4504:
4500:
4494:
4490:
4486:
4455:
4451:
4447:
4441:
4437:
4415:
4411:
4407:
4400:
4396:
4392:
4371:
4367:
4340:Darrellhenryite
4301:
4293:
4290:
4289:
4288:
4284:
4281:
4280:
4279:
4277:
4270:
4266:
4262:
4255:
4251:
4247:
4241:
4237:
4233:
4226:
4222:
4216:
4212:
4208:
4204:
4198:
4194:
4190:
4186:
4182:
4176:
4172:
4168:
4161:
4157:
4153:
4147:
4143:
4139:
4135:
4131:
4124:
4120:
4116:
4110:
4106:
4102:
4095:
4091:
4084:
4080:
4076:
4069:
4065:
4061:
4055:
4051:
4047:
4043:
4036:
4032:
4028:
4021:
4017:
4013:
4007:
4003:
3999:
3995:
3988:
3984:
3980:
3976:
3970:
3966:
3962:
3958:
3951:
3947:
3943:
3937:
3933:
3929:
3925:
3921:
3915:
3911:
3907:
3901:
3897:
3893:
3889:
3885:
3879:
3875:
3871:
3867:
3860:
3856:
3820:
3816:
3812:
3803:
3799:
3795:
3791:
3784:Neodymium-doped
3779:
3771:
3767:
3759:
3755:
3751:
3747:
3737:
3733:
3729:
3723:
3719:
3715:
3711:
3705:
3701:
3697:
3693:
3688:
3684:
3676:
3672:
3664:
3660:
3652:
3643:
3635:
3627:
3623:
3619:
3611:
3607:
3599:
3595:
3587:
3583:
3570:
3566:
3558:
3554:
3545:
3532:
3528:
3520:
3516:
3507:
3488:
3480:
3476:
3468:
3464:
3455:
3447:
3443:
3435:
3431:
3423:
3419:
3411:
3407:
3399:
3395:
3387:
3378:
3365:
3361:
3352:
3344:
3336:
3323:
3319:
3311:
3303:
3295:
3291:
3278:
3274:
3270:
3260:
3256:
3252:
3247:
3239:
3230:
3222:
3213:
3205:
3197:
3193:
3189:
3181:
3177:
3168:
3164:
3160:
3155:
3151:
3147:
3143:
3135:
3131:
3123:
3115:
3107:
3084:
3076:
3068:
3064:
3056:
3052:
3044:
3040:
3036:
3028:
3020:
3016:
3008:
3004:
2991:
2987:
2983:
2975:
2971:
2963:
2959:
2951:
2937:
2933:
2922:
2918:
2909:
2900:
2882:
2878:
2870:
2866:
2862:
2852:
2848:
2844:
2840:
2835:
2831:
2823:
2815:
2807:
2799:
2779:
2775:
2765:
2761:
2757:
2749:
2745:
2732:
2728:
2714:
2710:
2701:
2693:
2684:
2680:
2672:
2668:
2664:
2656:
2652:
2648:
2639:
2631:
2627:
2619:
2615:
2607:
2599:
2591:
2576:
2572:
2562:
2552:
2548:
2544:
2540:
2536:
2530:
2526:
2522:
2516:
2512:
2508:
2502:
2498:
2494:
2488:
2484:
2479:
2475:
2471:
2462:
2458:
2454:
2448:
2444:
2439:
2431:
2422:
2418:
2413:
2409:
2405:
2397:
2393:
2389:
2380:
2370:
2366:
2358:
2344:
2340:
2336:
2332:
2328:
2323:
2314:
2310:
2304:
2300:
2296:
2292:
2288:
2284:
2278:
2274:
2269:
2255:
2246:
2241:
2174:Organometallics
2159:
2157:Further reading
2154:
2153:
2118:
2114:
2087:
2083:
2058:
2054:
2031:
2027:
2014:
2010:
1986:
1982:
1969:
1965:
1955:
1953:
1945:
1944:
1940:
1932:
1922:Springer-Verlag
1914:
1903:
1880:
1876:
1866:
1864:
1849:
1845:
1840:
1831:Propynyllithium
1827:
1819:
1815:
1811:
1807:
1803:
1799:
1791:
1777:
1773:
1769:
1765:
1761:
1748:
1741:
1737:
1733:
1729:
1725:
1716:lithium hydride
1700:
1672:
1664:
1660:
1635:
1608:
1604:
1600:
1596:
1592:
1588:
1584:
1574:
1572:
1568:
1564:
1560:
1556:
1552:
1535:
1500:
1496:
1492:
1488:
1479:
1475:
1471:
1467:
1425:
1423:
1419:
1415:
1411:
1402:
1394:
1390:
1386:
1382:
1322:
1318:
1314:
1310:
1306:
1302:
1299:+ 2 TMEDA â 2 C
1298:
1294:
1290:
1286:
1282:
1261:tetrahydrofuran
1250:
1246:
1242:
1238:
1214:
1210:
1206:
1202:
1182:
1178:
1166:
1158:
1117:
1111:
1099:tetrahydrofuran
1072:
1064:
1042:
1038:
1034:
1030:
1026:
1022:
1018:
1014:
993:
953:
951:
947:
943:
939:
932:with Li metal:
918:
872:
865:
861:
837:
831:
823:lithium hydride
743:
739:
720:
713:
708:
707:
706: ?)
697:
693:
689:
685:
669:
659:
655:
648:
639:
636:
622:
621:
620:
619:
614:
610:
603:
596:
589:
585:
577:
555:
551:
523:
511:
509:Molecular shape
493:
479:, hydrocarbons
475:Ethers such as
462:
422:
420:
418:
406:
393:
387:
379:
365:
362:
357:
356:
345:
342:
341:
338:
332:
331:
328:
322:
321:
310:
292:
285:
276:
256:
243:
212:
192:
172:
159:
148:
135:
121:
119:
111:
109:
89:
86:
72:
57:
28:
23:
22:
15:
12:
11:
5:
4833:
4823:
4822:
4817:
4812:
4807:
4802:
4785:
4784:
4782:
4781:
4776:
4771:
4766:
4764:Lucifer yellow
4761:
4756:
4751:
4747:
4741:
4735:
4729:
4725:
4721:
4715:
4709:
4703:
4699:
4694:
4689:
4684:
4679:
4673:
4671:
4667:
4666:
4664:
4663:
4659:
4655:
4651:
4648:
4644:
4640:
4636:
4632:
4627:
4622:
4618:
4614:
4609:
4607:
4601:
4600:
4598:
4597:
4592:
4587:
4582:
4578:
4573:
4568:
4563:
4558:
4553:
4548:
4543:
4539:
4534:
4529:
4524:
4519:
4514:
4510:
4506:
4502:
4497:
4492:
4488:
4483:
4478:
4473:
4468:
4463:
4458:
4453:
4449:
4444:
4439:
4434:
4429:
4424:
4419:
4413:
4409:
4404:
4398:
4394:
4389:
4384:
4379:
4374:
4369:
4364:
4359:
4358:
4357:
4352:
4342:
4337:
4332:
4330:Cryolithionite
4327:
4322:
4317:
4311:
4309:
4303:
4302:
4300:
4299:
4291:
4282:
4274:
4268:
4264:
4259:
4253:
4249:
4244:
4239:
4235:
4230:
4224:
4219:
4214:
4210:
4206:
4201:
4196:
4192:
4188:
4184:
4179:
4174:
4170:
4165:
4159:
4155:
4150:
4145:
4141:
4137:
4133:
4128:
4122:
4118:
4113:
4108:
4104:
4099:
4093:
4088:
4082:
4078:
4073:
4067:
4063:
4058:
4053:
4049:
4045:
4040:
4034:
4030:
4025:
4019:
4015:
4010:
4005:
4001:
3997:
3992:
3986:
3982:
3978:
3973:
3968:
3964:
3960:
3955:
3949:
3945:
3940:
3935:
3931:
3927:
3923:
3918:
3913:
3909:
3904:
3899:
3895:
3891:
3887:
3882:
3877:
3873:
3869:
3864:
3858:
3853:
3852:
3851:
3849:Gilman reagent
3841:
3835:
3833:
3822:
3821:
3819:
3818:
3814:
3810:
3806:
3801:
3797:
3793:
3788:
3787:
3786:
3777:
3773:
3769:
3765:
3761:
3757:
3753:
3749:
3745:
3741:
3735:
3731:
3726:
3721:
3717:
3713:
3708:
3703:
3699:
3695:
3690:
3686:
3682:
3678:
3674:
3670:
3666:
3662:
3658:
3654:
3650:
3646:
3641:
3637:
3633:
3629:
3625:
3621:
3617:
3613:
3609:
3605:
3601:
3597:
3593:
3589:
3585:
3581:
3577:
3572:
3568:
3564:
3560:
3556:
3552:
3548:
3543:
3539:
3534:
3530:
3526:
3522:
3518:
3514:
3510:
3505:
3501:
3496:
3491:
3486:
3482:
3478:
3474:
3470:
3466:
3462:
3458:
3453:
3449:
3445:
3441:
3437:
3433:
3429:
3425:
3421:
3417:
3413:
3409:
3405:
3401:
3397:
3393:
3389:
3385:
3381:
3376:
3372:
3367:
3363:
3359:
3355:
3350:
3346:
3342:
3338:
3334:
3330:
3325:
3321:
3317:
3313:
3309:
3305:
3301:
3297:
3293:
3289:
3285:
3280:
3276:
3272:
3268:
3264:
3258:
3254:
3249:
3245:
3241:
3237:
3233:
3228:
3224:
3220:
3216:
3211:
3207:
3203:
3199:
3195:
3191:
3187:
3183:
3179:
3175:
3171:
3166:
3162:
3157:
3153:
3149:
3145:
3141:
3137:
3133:
3129:
3125:
3121:
3117:
3113:
3109:
3105:
3101:
3096:
3091:
3086:
3082:
3078:
3074:
3070:
3066:
3062:
3058:
3054:
3050:
3046:
3042:
3038:
3034:
3030:
3026:
3022:
3018:
3014:
3010:
3006:
3002:
2998:
2993:
2989:
2985:
2981:
2977:
2973:
2969:
2965:
2961:
2957:
2953:
2949:
2945:
2940:
2935:
2930:
2925:
2920:
2916:
2912:
2907:
2903:
2898:
2894:
2889:
2884:
2880:
2876:
2872:
2868:
2864:
2860:
2856:
2850:
2846:
2842:
2837:
2833:
2829:
2825:
2821:
2817:
2813:
2809:
2805:
2801:
2797:
2793:
2788:
2783:
2777:
2772:
2767:
2763:
2759:
2755:
2751:
2747:
2743:
2739:
2734:
2730:
2726:
2722:
2717:
2712:
2708:
2704:
2699:
2695:
2691:
2687:
2682:
2678:
2674:
2670:
2666:
2662:
2658:
2654:
2650:
2646:
2642:
2637:
2633:
2629:
2625:
2621:
2617:
2613:
2609:
2605:
2601:
2597:
2593:
2589:
2585:
2580:
2574:
2569:
2564:
2560:
2556:
2550:
2546:
2542:
2538:
2533:
2528:
2524:
2519:
2514:
2510:
2505:
2500:
2496:
2491:
2486:
2481:
2477:
2473:
2469:
2465:
2460:
2456:
2451:
2446:
2441:
2437:
2433:
2429:
2425:
2420:
2415:
2411:
2407:
2403:
2399:
2395:
2391:
2387:
2383:
2377:
2372:
2368:
2364:
2360:
2356:
2352:
2347:
2342:
2338:
2334:
2330:
2325:
2321:
2317:
2312:
2307:
2302:
2298:
2294:
2290:
2286:
2281:
2276:
2271:
2267:
2262:
2260:
2248:
2247:
2240:
2239:
2232:
2225:
2217:
2211:
2210:
2203:
2184:Ovaska, T. V.
2182:
2177:
2170:
2165:
2158:
2155:
2152:
2151:
2132:(2): 191â192.
2112:
2101:(7): 741â744.
2081:
2052:
2041:(2): 533â541.
2025:
2008:
1980:
1963:
1938:
1930:
1901:
1874:
1842:
1841:
1839:
1836:
1835:
1834:
1826:
1823:
1822:
1821:
1817:
1813:
1809:
1805:
1801:
1797:
1789:
1783:
1782:
1775:
1771:
1767:
1763:
1759:
1747:
1744:
1743:
1742:
1739:
1735:
1731:
1727:
1723:
1699:
1696:
1671:
1668:
1667:
1666:
1662:
1658:
1634:
1631:
1606:
1602:
1598:
1594:
1590:
1586:
1582:
1579:
1578:
1570:
1566:
1562:
1558:
1554:
1550:
1534:
1531:
1503:
1502:
1498:
1494:
1490:
1486:
1482:
1481:
1477:
1473:
1472:Br + RLi â 2 C
1469:
1465:
1430:
1429:
1421:
1417:
1413:
1409:
1401:
1398:
1397:
1396:
1392:
1388:
1384:
1380:
1324:
1323:
1320:
1316:
1312:
1308:
1304:
1300:
1296:
1292:
1288:
1284:
1280:
1253:
1252:
1248:
1244:
1240:
1236:
1212:
1208:
1204:
1200:
1180:
1176:
1164:
1156:
1145:delocalization
1141:conjugate base
1125:Brønsted acids
1113:Main article:
1110:
1107:
1070:
1063:
1060:
1045:
1044:
1040:
1036:
1032:
1028:
1024:
1020:
1016:
1012:
997:polymerization
992:
989:
958:
957:
949:
945:
941:
937:
930:1-chlorobutane
917:
914:
870:
863:
859:
833:Main article:
830:
827:
757:polymerization
741:
737:
718:
715:
714:
709:
687:
686:
682:standard state
679:
676:
675:
670:
667:
664:
663:
640:
632:
629:
628:
624:
623:
611:
604:
597:
590:
575:
574:
573:
572:
570:
561:
560:
552:
549:
546:
545:
536:
535:
531:
530:
524:
519:
516:
515:
512:
507:
504:
503:
499:
498:
495:
491:
481:
480:
473:
467:
466:
463:
458:
455:
454:
451:
445:
444:
441:
435:
434:
431:
425:
424:
415:
411:
410:
404:
398:
397:
391:
385:
380:
375:
372:
371:
367:
366:
364:
363:
360:
352:
351:
350:
347:
346:
344:
343:
339:
336:
335:
333:
329:
326:
325:
317:
316:
315:
312:
311:
309:
308:
295:
293:
281:
278:
277:
275:
274:
266:
264:
258:
257:
255:
254:
246:
244:
236:
233:
232:
222:
214:
213:
211:
210:
202:
200:
194:
193:
191:
190:
182:
180:
174:
173:
171:
170:
162:
160:
153:
150:
149:
147:
146:
138:
136:
131:
128:
127:
123:
122:
120:1-lithiobutane
117:
113:
112:
107:
102:
96:
95:
91:
90:
87:
78:
77:
74:
73:
67:
58:
52:
36:-Butyllithium
26:
18:N-butyllithium
9:
6:
4:
3:
2:
4832:
4821:
4818:
4816:
4813:
4811:
4808:
4806:
4803:
4801:
4798:
4797:
4795:
4780:
4777:
4775:
4772:
4770:
4767:
4765:
4762:
4760:
4757:
4755:
4752:
4750:
4744:
4738:
4732:
4726:
4724:
4718:
4712:
4706:
4700:
4698:
4695:
4693:
4690:
4688:
4685:
4683:
4680:
4678:
4675:
4674:
4672:
4668:
4649:
4647:
4641:
4639:
4633:
4631:
4628:
4626:
4623:
4621:
4611:
4610:
4608:
4606:
4602:
4596:
4593:
4591:
4588:
4586:
4574:
4572:
4564:
4562:
4559:
4557:
4554:
4552:
4549:
4547:
4535:
4533:
4530:
4528:
4525:
4523:
4520:
4518:
4498:
4496:
4484:
4482:
4479:
4477:
4474:
4472:
4469:
4467:
4464:
4462:
4459:
4457:
4445:
4443:
4435:
4433:
4430:
4428:
4425:
4423:
4420:
4418:
4405:
4403:
4390:
4388:
4387:Hsianghualite
4385:
4383:
4380:
4378:
4375:
4373:
4365:
4363:
4360:
4356:
4353:
4351:
4348:
4347:
4346:
4343:
4341:
4338:
4336:
4333:
4331:
4328:
4326:
4323:
4321:
4318:
4316:
4313:
4312:
4310:
4308:
4304:
4298:
4275:
4273:
4260:
4258:
4245:
4243:
4231:
4229:
4220:
4218:
4202:
4200:
4180:
4178:
4166:
4164:
4151:
4149:
4129:
4127:
4114:
4112:
4100:
4098:
4089:
4087:
4074:
4072:
4059:
4057:
4041:
4039:
4026:
4024:
4011:
4009:
3993:
3991:
3974:
3972:
3956:
3954:
3941:
3939:
3919:
3917:
3905:
3903:
3883:
3881:
3865:
3863:
3854:
3850:
3847:
3846:
3845:
3842:
3840:
3837:
3836:
3834:
3831:
3827:
3823:
3817:
3807:
3805:
3789:
3785:
3782:
3781:
3780:
3774:
3772:
3762:
3760:
3742:
3740:
3727:
3725:
3709:
3707:
3691:
3689:
3679:
3677:
3667:
3665:
3655:
3653:
3647:
3645:
3638:
3636:
3630:
3628:
3614:
3612:
3602:
3600:
3590:
3588:
3578:
3576:
3573:
3571:
3561:
3559:
3549:
3547:
3540:
3538:
3535:
3533:
3523:
3521:
3511:
3509:
3502:
3500:
3497:
3495:
3492:
3490:
3483:
3481:
3471:
3469:
3459:
3457:
3450:
3448:
3438:
3436:
3426:
3424:
3414:
3412:
3402:
3400:
3390:
3388:
3382:
3380:
3373:
3371:
3368:
3366:
3356:
3354:
3347:
3345:
3339:
3337:
3331:
3329:
3326:
3324:
3314:
3312:
3306:
3304:
3298:
3296:
3286:
3284:
3281:
3279:
3265:
3263:
3250:
3248:
3242:
3240:
3234:
3232:
3225:
3223:
3217:
3215:
3208:
3206:
3200:
3198:
3184:
3182:
3172:
3170:
3158:
3156:
3138:
3136:
3126:
3124:
3118:
3116:
3110:
3108:
3102:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3079:
3077:
3071:
3069:
3059:
3057:
3047:
3045:
3031:
3029:
3023:
3021:
3011:
3009:
2999:
2997:
2994:
2992:
2978:
2976:
2966:
2964:
2954:
2952:
2946:
2944:
2941:
2939:
2931:
2929:
2926:
2924:
2913:
2911:
2904:
2902:
2895:
2893:
2890:
2888:
2885:
2883:
2873:
2871:
2857:
2855:
2838:
2836:
2826:
2824:
2818:
2816:
2810:
2808:
2802:
2800:
2794:
2792:
2789:
2787:
2784:
2782:
2773:
2771:
2768:
2766:
2752:
2750:
2740:
2738:
2735:
2733:
2723:
2721:
2718:
2716:
2705:
2703:
2696:
2694:
2688:
2686:
2675:
2673:
2659:
2657:
2643:
2641:
2634:
2632:
2622:
2620:
2610:
2608:
2602:
2600:
2594:
2592:
2586:
2584:
2581:
2579:
2570:
2568:
2565:
2563:
2557:
2555:
2534:
2532:
2520:
2518:
2506:
2504:
2492:
2490:
2482:
2480:
2466:
2464:
2452:
2450:
2442:
2440:
2434:
2432:
2426:
2424:
2416:
2414:
2400:
2398:
2384:
2382:
2378:
2376:
2373:
2371:
2361:
2359:
2353:
2351:
2348:
2346:
2326:
2324:
2318:
2316:
2308:
2306:
2282:
2280:
2272:
2270:
2264:
2263:
2261:
2258:
2253:
2249:
2245:
2238:
2233:
2231:
2226:
2224:
2219:
2218:
2215:
2208:
2204:
2202:
2198:
2194:
2190:
2189:
2183:
2181:
2178:
2175:
2171:
2169:
2166:
2164:
2161:
2160:
2147:
2143:
2139:
2135:
2131:
2127:
2123:
2116:
2108:
2104:
2100:
2096:
2092:
2085:
2077:
2073:
2069:
2065:
2064:
2056:
2048:
2044:
2040:
2036:
2029:
2022:
2018:
2012:
2004:
2000:
1996:
1992:
1984:
1977:
1976:3-527-29390-6
1973:
1967:
1952:
1948:
1942:
1933:
1931:3-540-16916-4
1927:
1923:
1919:
1912:
1910:
1908:
1906:
1897:
1893:
1889:
1885:
1878:
1863:on 9 May 2017
1862:
1858:
1854:
1847:
1843:
1832:
1829:
1828:
1795:
1794:
1793:
1786:
1781:
1757:
1756:
1755:
1753:
1730:Li â LiH + CH
1721:
1720:
1719:
1717:
1713:
1709:
1705:
1702:When heated,
1695:
1693:
1689:
1688:freezing bath
1685:
1681:
1677:
1656:
1655:
1654:
1652:
1648:
1644:
1640:
1630:
1628:
1624:
1620:
1616:
1612:
1548:
1547:
1546:
1544:
1540:
1530:
1528:
1524:
1520:
1516:
1512:
1510:
1484:
1483:
1463:
1462:
1461:
1459:
1455:
1451:
1447:
1443:
1439:
1435:
1407:
1406:
1405:
1378:
1375:
1374:
1373:
1371:
1367:
1363:
1358:
1356:
1352:
1348:
1345:. While some
1344:
1340:
1338:
1332:
1328:
1278:
1277:
1276:
1274:
1270:
1266:
1262:
1258:
1234:
1233:
1232:
1230:
1229:deprotonation
1226:
1222:
1218:
1198:
1194:
1190:
1186:
1174:
1170:
1162:
1154:
1150:
1146:
1142:
1138:
1134:
1130:
1126:
1122:
1116:
1106:
1104:
1103:diethyl ether
1100:
1096:
1092:
1088:
1084:
1080:
1076:
1069:
1059:
1057:
1053:
1049:
1010:
1009:
1008:
1006:
1002:
998:
988:
986:
982:
977:
975:
971:
967:
963:
935:
934:
933:
931:
927:
926:1-bromobutane
923:
913:
911:
907:
903:
899:
895:
891:
887:
882:
880:
876:
868:
857:
853:
849:
845:
841:
836:
826:
824:
820:
815:
813:
809:
808:diethyl ether
805:
801:
797:
793:
789:
784:
782:
778:
774:
770:
766:
765:polybutadiene
762:
758:
754:
750:
748:
735:
734:-Butyllithium
733:
724:
712:
705:
700:
683:
677:
674:
671:
666:
665:
662:
661:methyllithium
658:
654:
653:-butyllithium
652:
647:
646:-butyllithium
645:
641:
638:
635:organolithium
631:
630:
625:
618:
609:
602:
595:
571:
568:
567:
563:
562:
559:
553:
548:
547:
543:
542:
537:
532:
529:
525:
522:
521:Dipole moment
518:
517:
513:
510:
506:
505:
500:
496:
490:
486:
483:
482:
478:
474:
472:
469:
468:
464:
461:
457:
456:
452:
450:
449:Boiling point
447:
446:
442:
440:
439:Melting point
437:
436:
432:
430:
427:
426:
416:
413:
412:
405:
403:
400:
399:
381:
378:
374:
373:
368:
359:
358:
355:
348:
334:
324:
323:
320:
313:
305:
301:
300:DTXSID1026821
297:
296:
294:
284:
280:
279:
272:
268:
267:
265:
263:
260:
259:
252:
248:
247:
245:
239:
235:
234:
230:
226:
223:
221:
219:ECHA InfoCard
216:
215:
208:
204:
203:
201:
199:
196:
195:
188:
184:
183:
181:
179:
176:
175:
168:
164:
163:
161:
157:
152:
151:
144:
140:
139:
137:
134:
130:
129:
124:
114:
106:
101:
97:
92:
84:
79:
70:
63:
59:
55:
48:
44:
43:
39:
35:
30:
19:
4754:Lithium soap
4742:
4736:
4730:
4716:
4710:
4704:
4692:Lithium atom
4605:Hypothetical
4320:Berezanskite
4027:
2206:
2192:
2185:
2173:
2129:
2125:
2115:
2098:
2094:
2084:
2067:
2061:
2055:
2038:
2034:
2028:
2011:
1994:
1990:
1983:
1966:
1954:. Retrieved
1950:
1941:
1917:
1887:
1883:
1877:
1865:. Retrieved
1861:the original
1856:
1846:
1787:
1784:
1751:
1749:
1703:
1701:
1680:acetaldehyde
1673:
1657:RLi + RCONMe
1638:
1636:
1580:
1536:
1526:
1522:
1518:
1514:
1513:rather than
1508:
1504:
1457:
1449:
1445:
1431:
1403:
1376:
1369:
1361:
1359:
1354:
1350:
1346:
1336:
1325:
1256:
1254:
1196:
1172:
1160:
1152:
1148:
1136:
1132:
1128:
1120:
1118:
1082:
1067:
1065:
1046:
994:
991:Applications
978:
959:
956:(X = Cl, Br)
921:
919:
905:
897:
883:
874:
855:
854:with Li and
843:
839:
838:
818:
816:
785:
746:
745:
731:
730:
729:
657:hexyllithium
650:
643:
565:
550:Main hazards
539:
488:
423:as solution
126:Identifiers
116:Other names
104:
68:
53:
33:
29:
4595:Zinnwaldite
4461:Manandonite
4427:Lavinskyite
4335:Darapiosite
4325:Brannockite
4315:Amblygonite
2640:CH(OH)COOLi
1710:to produce
1609:Cl). Other
1428:(X = Br, I)
1416:Li + RX â C
1343:metalations
1075:nucleophile
952:Li + LiX
916:Preparation
892:(2.55) and
879:Lewis acids
867:tetrahedron
848:cyclohexane
544:(OHS/OSH):
414:Appearance
370:Properties
225:100.003.363
187:CHEBI:51469
4810:Superbases
4794:Categories
4643:(HeO)(LiF)
4590:Zektzerite
4561:Tourmaline
4532:Sogdianite
4522:Rossmanite
4432:Lepidolite
4377:Faizievite
4362:Emeleusite
1920:. Berlin:
1838:References
1615:metalloids
1383:NH + (MeO)
1335:potassium
1221:volatility
1217:enolizable
1189:thiophenes
1109:Metalation
1095:metalation
1003:, such as
761:elastomers
502:Structure
471:Solubility
402:Molar mass
271:09W9A6B8ZC
198:ChemSpider
154:3D model (
133:CAS Number
118:NBL, BuLi,
100:IUPAC name
4687:LB buffer
4556:Tiptopite
4527:Saliotite
4476:Neptunite
4471:Nambulite
4382:Hectorite
2252:Inorganic
2146:1369-9261
1956:17 August
1643:aldehydes
1627:tellurium
1448:-BuBr or
1379:-BuLi + R
1366:carbamate
1339:-butoxide
1331:superbase
1267:(TMEDA),
1243:+ RH â C
1193:ferrocene
1079:reductant
1062:Reactions
1039:âCH=CHâCH
1023:=CHâCH=CH
1005:butadiene
981:titration
779:) in the
777:superbase
4551:Sugilite
4481:Olympite
4307:Minerals
3908:LiN(SiMe
1857:Org@Work
1825:See also
1712:1-butene
1684:ethylene
1665:+ RC(O)R
1623:selenium
1561:SnAr â C
1480:R + LiBr
1424:X + RLi
1368:, where
1169:dithiane
1056:ethylene
1048:Isoprene
985:biphenyl
936:2 Li + C
804:heptanes
794:such as
763:such as
751:) is an
637:reagents
633:Related
566:NFPA 704
534:Hazards
419:unstable
207:10254339
143:109-72-8
4774:NASICON
4422:Kunzite
4345:Elbaite
4234:LiOC(CH
3828: (
3826:Organic
2573:LiBr¡2H
2186:e-EROS
1804:Li + CO
1718:(LiH):
1692:dry ice
1661:â LiNMe
1647:ketones
1619:mercury
1601:Br or C
1573:+ LiAr
1557:Li + Me
1319:(TMEDA)
1291:+ 2 LiC
1263:(THF),
1223:of the
1167:, e.g.
1163:âCH(SR)
1019:Li + CH
966:benzene
944:X â C
894:lithium
800:hexanes
796:pentane
792:alkanes
704:what is
702: (
485:Acidity
429:Density
238:PubChem
4630:LiFHeO
4048:CHLiCH
3300:LiNaNO
2943:FLiNaK
2934:LiFePO
2776:LiCl¡H
2275:LiAlCl
2257:(list)
2254:
2144:
1974:
1928:
1867:26 May
1766:Li + H
1746:Safety
1651:amides
1625:, and
1611:metals
1575:
1426:
1387:CO â R
1307:+ Fe(C
1225:butane
1185:furans
1087:amines
1001:dienes
970:octane
962:sodium
954:
912:, Li.
910:cation
890:carbon
802:, and
699:verify
696:
354:SMILES
94:Names
4652:2/3-x
4625:HLiHe
4505:Li)Al
3959:LiN(C
3861:COOLi
3830:soaps
3632:LiTaO
3494:LiSCN
3308:LiNbO
3081:LiHSO
3073:LiHSO
3025:LiHCO
2948:LiGaH
2928:FLiBe
2875:CsLiB
2820:LiCoO
2812:LiClO
2804:LiClO
2796:LiClO
2786:LiClO
2737:LiCNO
2690:LiCHO
2677:Li(CH
2604:LiBrO
2596:LiBrO
2588:LiBrO
2583:LiBrO
2559:LiBSi
2485:LiAsF
2402:LiB(C
2386:LiB(C
2355:LiAsF
2320:LiAlO
2311:LiAlH
1770:O â C
1738:CH=CH
1676:TMEDA
1511:-BuLi
1442:vinyl
1432:This
1329:is a
1273:DABCO
1251:+ RLi
902:anion
749:-BuLi
453:80 C
407:64.06
319:InChI
251:61028
178:ChEBI
156:JSmol
4728:LiNi
4702:LiNi
4635:LiHe
4223:LiEt
4187:C(CH
3876:LiNO
3792:LiZr
3776:LiYF
3730:LiVO
3712:LiTi
3649:LiTe
3575:LiSi
3504:LiSO
3499:LiSH
3384:LiPF
3370:LiOH
3292:NaPO
3283:LiNa
3253:LiNO
3244:LiNO
3236:LiNO
3219:LiNH
3161:LiMn
3120:LiIO
3112:LiIO
3104:LiIO
3099:LiIO
3089:LiHe
3037:H(CO
3017:HAsO
2980:LiGe
2791:LiFO
2770:LiCl
2720:LiCN
2698:LiCH
2624:LiCF
2567:LiBr
2445:LiBO
2436:LiBH
2428:LiBF
2419:LiWF
2375:LiAt
2350:LiAs
2329:LiAl
2142:ISSN
1972:ISBN
1958:2023
1926:ISBN
1869:2017
1780:LiOH
1714:and
1682:and
1645:and
1613:and
1589:SnMe
1569:SnMe
1438:aryl
1279:Fe(C
1195:(Fe(
1191:and
1101:and
1091:base
1077:and
974:LiCl
810:and
773:base
651:tert
558:LiOH
361:CCCC
262:UNII
4658:TiO
4296:COO
4278:LiC
4263:LiC
4256:LiN
4213:LiO
4183:LiO
4169:LiC
4140:LiN
4103:LiC
4085:BLi
4070:CLi
4062:(CH
4004:LiO
3989:PLi
3886:LiC
3813:ZrO
3796:(PO
3752:(PO
3734:¡2H
3716:(PO
3685:TiO
3673:TeO
3661:TeO
3608:SiO
3596:SiO
3584:SiF
3567:SeO
3555:SeO
3477:RuO
3465:PtO
3420:HPO
3408:HPO
3341:LiO
3333:LiO
3328:LiO
3320:NbO
3202:LiN
3188:0.9
3178:MoO
3132:IrO
3094:LiI
3061:LiH
3049:LiH
3005:AsO
3001:LiH
2996:LiH
2984:(PO
2972:GeO
2960:GeF
2906:LiF
2892:LiF
2887:LiD
2849:¡2H
2845:CrO
2832:CrO
2707:LiC
2661:LiC
2653:ClO
2645:LiC
2549:¡5H
2527:ZrF
2513:TiF
2499:SnF
2455:LiB
2367:AsO
2337:(PO
2335:2âx
2331:1+x
2297:(PO
2295:2âx
2287:1+x
2197:doi
2134:doi
2103:doi
2072:doi
2068:512
2043:doi
2017:doi
1999:doi
1892:doi
1808:â C
1690:of
1543:tin
1485:2 C
1464:2 C
1391:NCO
1315:Li)
1235:LiC
1207:)(C
1183:),
1175:âCH
1155:âCH
1035:âCH
1027:â C
999:of
928:or
888:of
812:THF
767:or
644:sec
477:THF
288:EPA
241:CID
4796::
4740:Co
4734:Mn
4714:Al
4708:Co
4662:He
4656:3x
4654:Li
4650:La
4617:Be
4613:Li
4581:CO
4515:18
4509:Si
4493:10
4452:PO
4401:OH
4292:23
4283:11
4254:18
4227:BH
4195:CH
4193:16
4173:CH
4162:Li
4125:Li
4123:11
4105:10
4096:Li
4092:CH
4083:28
4079:12
4052:CH
4044:CH
4037:Li
4022:Li
4020:13
4002:35
3998:18
3977:(C
3952:Li
3922:Li
3894:NO
3857:CH
3809:Li
3768:WO
3764:Li
3744:Li
3704:12
3698:Ti
3694:Li
3681:Li
3669:Li
3657:Li
3644:Te
3640:Li
3620:Si
3616:Li
3604:Li
3592:Li
3580:Li
3563:Li
3551:Li
3546:Se
3542:Li
3537:Li
3529:SO
3525:Li
3517:SO
3513:Li
3485:Li
3473:Li
3461:Li
3456:Po
3452:Li
3444:PO
3440:Li
3432:PO
3428:Li
3416:Li
3404:Li
3396:PO
3392:Li
3375:Li
3358:Li
3349:Li
3316:Li
3288:Li
3267:Li
3257:¡H
3231:NH
3227:Li
3210:Li
3196:17
3190:Mo
3186:Li
3174:Li
3154:12
3148:Zr
3144:La
3140:Li
3128:Li
3065:PO
3053:PO
3033:Li
3013:Li
2968:Li
2956:Li
2923:Al
2915:Li
2910:Al
2897:Li
2881:10
2863:Cr
2859:Li
2841:Li
2828:Li
2754:Li
2746:CO
2742:Li
2729:CN
2725:Li
2669:IO
2636:CH
2628:SO
2612:Li
2537:Li
2523:Li
2509:Li
2495:Li
2468:Li
2381:Li
2363:Li
2333:Ti
2293:Ge
2289:Al
2285:Li
2266:Li
2140:.
2130:26
2128:.
2124:.
2099:25
2097:.
2093:.
2066:.
2039:42
2037:.
1995:48
1993:.
1949:.
1924:.
1904:^
1888:18
1886:.
1855:.
1820:Li
1816:CO
1778:+
1776:10
1734:CH
1653::
1629:.
1621:,
1545::
1499:10
1305:10
1249:10
1199:âC
1187:,
1179:PR
1149:Hâ
1127:.
1043:Li
976:.
904:,
881:.
798:,
526:0
494:)
487:(p
395:Li
4748:2
4746:O
4743:z
4737:y
4731:x
4722:2
4720:O
4717:z
4711:y
4705:x
4660:3
4645:2
4637:2
4619:y
4615:x
4583:3
4579:2
4569:4
4544:2
4542:)
4540:3
4513:O
4511:6
4507:2
4503:2
4491:0
4489:4
4454:4
4450:3
4440:4
4416:)
4414:6
4412:O
4410:2
4399:7
4397:O
4395:3
4370:4
4287:H
4269:3
4267:H
4265:2
4252:H
4250:9
4248:C
4240:3
4238:)
4236:3
4225:3
4215:4
4211:5
4209:H
4207:4
4205:C
4197:3
4191:)
4189:2
4185:2
4175:3
4171:2
4160:5
4158:H
4156:6
4154:C
4146:4
4144:O
4142:2
4138:3
4136:H
4134:5
4132:C
4121:H
4119:5
4117:C
4109:8
4107:H
4094:3
4081:H
4077:C
4068:3
4066:)
4064:3
4054:3
4050:2
4046:3
4035:9
4033:H
4031:4
4029:C
4018:H
4016:6
4014:C
4006:3
4000:H
3996:C
3987:2
3985:)
3983:5
3981:H
3979:6
3969:2
3967:)
3965:7
3963:H
3961:3
3950:5
3948:H
3946:5
3944:C
3936:7
3934:O
3932:5
3930:H
3928:6
3926:C
3924:3
3914:2
3912:)
3910:3
3900:2
3898:S
3896:4
3892:6
3890:F
3888:2
3878:4
3874:6
3872:H
3870:4
3868:C
3859:3
3832:)
3815:3
3811:2
3802:3
3800:)
3798:4
3794:2
3778:4
3770:4
3766:2
3758:3
3756:)
3754:4
3750:2
3748:V
3746:3
3738:O
3736:2
3732:3
3722:3
3720:)
3718:4
3714:2
3702:O
3700:5
3696:4
3687:3
3683:2
3675:4
3671:2
3663:3
3659:2
3651:3
3642:2
3634:3
3626:5
3624:O
3622:2
3618:2
3610:3
3606:2
3598:4
3594:4
3586:6
3582:2
3569:4
3565:2
3557:3
3553:2
3544:2
3531:4
3527:2
3519:3
3515:2
3508:F
3506:3
3489:S
3487:2
3479:3
3475:2
3467:3
3463:2
3454:2
3446:4
3442:3
3434:3
3430:3
3422:4
3418:2
3410:3
3406:2
3398:4
3394:3
3386:6
3379:P
3377:3
3364:2
3362:O
3360:2
3353:O
3351:2
3343:3
3335:2
3322:3
3318:2
3310:3
3302:2
3294:3
3290:2
3277:2
3275:O
3273:2
3271:N
3269:2
3261:O
3259:2
3255:3
3246:3
3238:2
3229:2
3221:2
3214:N
3212:3
3204:3
3194:O
3192:6
3180:4
3176:2
3167:4
3165:O
3163:2
3152:O
3150:2
3146:3
3142:7
3134:3
3130:2
3122:4
3114:3
3106:2
3083:4
3075:3
3067:4
3063:2
3055:3
3051:2
3043:2
3041:)
3039:3
3035:3
3027:3
3019:4
3015:2
3007:4
3003:2
2990:3
2988:)
2986:4
2982:2
2974:3
2970:2
2962:6
2958:2
2950:4
2936:4
2921:6
2919:F
2917:3
2908:4
2901:F
2899:2
2879:O
2877:6
2869:7
2867:O
2865:2
2861:2
2853:O
2851:2
2847:4
2843:2
2834:4
2830:2
2822:2
2814:4
2806:3
2798:2
2780:O
2778:2
2764:4
2762:O
2760:2
2758:C
2756:2
2748:3
2744:2
2731:2
2727:2
2715:O
2713:5
2711:H
2709:2
2702:O
2700:3
2692:2
2685:N
2683:2
2681:)
2679:3
2671:2
2667:3
2665:H
2663:2
2655:2
2651:2
2649:H
2647:2
2638:3
2630:3
2626:3
2618:2
2616:C
2614:2
2606:4
2598:3
2590:2
2577:O
2575:2
2561:2
2553:O
2551:2
2547:7
2545:O
2543:4
2541:B
2539:2
2529:6
2525:2
2515:6
2511:2
2501:6
2497:2
2487:6
2478:7
2476:O
2474:4
2472:B
2470:2
2461:5
2459:O
2457:3
2447:2
2438:4
2430:4
2421:6
2412:4
2410:)
2408:5
2406:F
2404:6
2396:2
2394:)
2392:4
2390:O
2388:2
2369:4
2365:3
2357:6
2343:3
2341:)
2339:4
2322:2
2313:4
2303:3
2301:)
2299:4
2291:x
2277:4
2268:2
2236:e
2229:t
2222:v
2199::
2193:n
2191:"
2148:.
2136::
2109:.
2105::
2078:.
2074::
2049:.
2045::
2023:.
2019::
2005:.
2001::
1978:.
1960:.
1936:.
1934:.
1898:.
1894::
1871:.
1818:2
1814:9
1812:H
1810:4
1806:2
1802:9
1800:H
1798:4
1796:C
1790:2
1774:H
1772:4
1768:2
1764:9
1762:H
1760:4
1758:C
1752:n
1740:2
1736:2
1732:3
1728:9
1726:H
1724:4
1722:C
1704:n
1663:2
1659:2
1639:n
1607:9
1605:H
1603:4
1599:9
1597:H
1595:4
1591:3
1587:9
1585:H
1583:4
1571:3
1567:9
1565:H
1563:4
1559:3
1555:9
1553:H
1551:4
1549:C
1527:t
1523:t
1519:t
1515:n
1509:t
1497:H
1495:4
1491:9
1489:H
1487:4
1478:9
1476:H
1474:4
1470:9
1468:H
1466:4
1458:n
1450:n
1446:n
1422:9
1420:H
1418:4
1414:9
1412:H
1410:4
1408:C
1393:2
1389:2
1385:2
1381:2
1377:n
1370:n
1362:n
1355:n
1351:n
1347:n
1337:t
1321:2
1317:2
1313:4
1311:H
1309:5
1303:H
1301:4
1297:9
1295:H
1293:4
1289:2
1287:)
1285:5
1283:H
1281:5
1257:n
1247:H
1245:4
1241:9
1239:H
1237:4
1213:5
1211:H
1209:5
1205:4
1203:H
1201:5
1197:H
1181:2
1177:2
1173:H
1165:2
1161:H
1157:2
1153:H
1137:n
1133:s
1129:t
1121:n
1083:n
1071:b
1068:K
1041:2
1037:2
1033:9
1031:H
1029:4
1025:2
1021:2
1017:9
1015:H
1013:4
1011:C
950:9
948:H
946:4
942:9
940:H
938:4
922:n
906:n
898:n
875:n
871:4
864:4
860:2
858:H
856:C
844:n
840:n
819:n
788:M
775:(
747:n
742:9
740:H
738:4
736:C
732:n
694:Y
615:W
607:3
600:4
593:3
528:D
492:a
489:K
392:9
389:H
386:4
383:C
290:)
286:(
158:)
108:3
105:Îź
69:n
54:n
34:n
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
