64:
1056:
426:
271:
2591:
799:
48:
38:
794:
804:
784:
789:
2341:
1051:
2499:
1264:
1054:
1055:
2709:, with a theoretical decomposition energy of about 5 kJ/g, and aqueous solutions above 80% can be easily detonated by detonator or strong heating under confinement. At least two factories dealing in hydroxylamine have been destroyed since 1999 with loss of life. It is known, however, that ferrous and ferric
2627:
Hydroxylamine can also be used to better characterize the nature of a post-translational modification onto proteins. For example, poly(ADP-Ribose) chains are sensitive to hydroxylamine when attached to glutamic or aspartic acids but not sensitive when attached to serines. Similarly, Ubiquitin
2192:
This reaction is useful in the purification of ketones and aldehydes: if hydroxylamine is added to an aldehyde or ketone in solution, an oxime forms, which generally precipitates from solution; heating the precipitate with an inorganic acid then restores the original aldehyde or ketone.
2559:
are seemingly able to modify other regions of the DNA & lead to other types of mutations. This may be due to the ability of hydroxylamine to undergo uncontrolled free radical chemistry in the presence of trace metals and oxygen, in fact in the absence of its free radical affects
1079:
2564:
noted hydroxylamine was unable to induce reversion mutations of its C:G to T:A transition effect & even considered hydroxylamine to be the most specific mutagen known. Practically, it has been largely surpassed by more potent mutagens such as
2623:
Some non-chemical uses include removal of hair from animal hides and photographic developing solutions. In the semiconductor industry, hydroxylamine is often a component in the "resist stripper", which removes photoresist after lithography.
812:
3167:
Zhang, Xiaoping; Su, Rui; Li, Jingling; Huang, Liping; Yang, Wenwen; Chingin, Konstantin; Balabin, Roman; Wang, Jingjing; Zhang, Xinglei; Zhu, Weifeng; Huang, Keke; Feng, Shouhua; Chen, Huanwen (2024).
3344:
Kirby, AJ; Davies, JE; Fox, DJ; Hodgson, DR; Goeta, AE; Lima, MF; Priebe, JP; Santaballa, JA; Nome, F (28 February 2010). "Ammonia oxide makes up some 20% of an aqueous solution of hydroxylamine".
2406:
Similarly to amines, one can distinguish hydroxylamines by their degree of substitution: primary, secondary and tertiary. When stored exposed to air for weeks, secondary hydroxylamines degrade to
764:
3825:
Arciero, David M.; Hooper, Alan B.; Cai, Mengli; Timkovich, Russell (1993-09-01). "Evidence for the structure of the active site heme P460 in hydroxylamine oxidoreductase of
Nitrosomonas".
63:
3523:
Busby, Stephen; Irani, Meher; de
Crombrugghe, BenoΓt (1982). "Isolation of mutant promoters in the Escherichia coli galactose operon using local mutagenesis on cloned DNA fragments".
2259:
can easily explode aqueous solutions concentrated above 80% by weight, and even 50% solution might prove detonable if tested in bulk. In air, the combustion is rapid and complete:
946:
4009:
Cisneros, L. O.; Rogers, W. J.; Mannan, M. S.; Li, X.; Koseki, H. (2003). "Effect of Iron Ion in the
Thermal Decomposition of 50 mass% Hydroxylamine/Water Solutions".
1057:
2555:
to hydroxyaminocytidine, which is misread as thymidine, thereby inducing C:G to T:A transition mutations. But high concentrations or over-reaction of hydroxylamine
1065:
2540:
Hydroxylamine and its salts are commonly used as reducing agents in myriad organic and inorganic reactions. They can also act as antioxidants for fatty acids.
2065:
1277:
37:
3083:
2811:
3976:
1387:
4087:
4716:
4740:
4732:
2628:
molecules bound to serines or threonines residues are sensitive to hydroxylamine, but those bound to lysine (isopeptide bond) are resistant.
4124:
3992:
475:
4092:
2577:, but being a very small mutagenic compound with high specificity, it found some specialized uses such as mutation of DNA packed within
3477:
Waugh, Robbie; Leader, David J.; McCallum, Nicola; Caldwell, David (2006). "Harvesting the potential of induced biological diversity".
1431:) can be produced via several routes but only two are commercially viable. It is also produced naturally as discussed in a section on
1072:
3312:
942:
3952:
3575:
3428:
3251:
2868:
2830:
2795:
733:
3148:
3760:"The E3 ligase HOIL-1 catalyses ester bond formation between ubiquitin and components of the Myddosome in mammalian cells"
1272:
47:
3322:
3062:
2907:"Structural conservation of the B subunit in the ammonia monooxygenase/particulate methane monooxygenase superfamily"
2843:
440:
4117:
1284:
4838:
3100:
3693:
Langelier, Marie-France; Billur, Ramya; Sverzhinsky, Aleksandr; Black, Ben E.; Pascal, John M. (2021-11-18).
2219:
1535:
1239:
934:
334:
2594:
This route also involves the
Beckmann Rearrangement, like the conversion from cyclohexanone to caprolactam.
880:
383:
266:
4051:
3695:"HPF1 dynamically controls the PARP1/2 balance between initiating and elongating ADP-ribose modifications"
2457:
is the most common method to synthesize hydroxylamines. Care must be taken to prevent over-oxidation to a
2285:
Absent air, pure hydroxylamine requires stronger heating and the detonation does not complete combustion:
803:
228:
4110:
3870:"Nitrosomonas europaea cytochrome P460 is a direct link between nitrification and nitrous oxide emission"
2574:
2057:
404:
926:
798:
4853:
4823:
2779:
2662:
890:
793:
618:
592:
3271:
4828:
2389:
2163:
1835:
1367:
1215:
1167:
982:
278:
918:
4848:
2776:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
2357:
1642:
1408:(zinc dichloride di(hydroxylamine)), known as Crismer's salt, releases hydroxylamine upon heating.
1177:
1172:
1102:
1018:
421:
328:
4833:
4072:, Coll. Vol. 6, p. 943; Vol. 58, p. 32. (preparation of hydroxylamine-O-sulfonic acid).
3123:
3045:
Walker, John E.; Howell, David M. (1967). "Dichlorobis(hydroxylamine)zinc(II) (Crismer's Salt)".
2694:
664:
3989:
3758:
Kelsall, Ian R.; Zhang, Jiazhen; Knebel, Axel; Arthur, J. Simon C.; Cohen, Philip (2019-07-02).
1136:
408 mg/kg (oral, mouse); 59β70 mg/kg (intraperitoneal mouse, rat); 29 mg/kg (subcutaneous, rat)
783:
188:
4619:
4164:
2566:
2521:
2503:
1899:
868:
709:
3667:
3237:
3024:
3003:
2962:
788:
4843:
4695:
4598:
4214:
4068:
M. W. Rathke A. A. Millard "Boranes in
Functionalization of Olefins to Amines: 3-Pinanamine"
3178:
2666:
2648:
2644:
826:
776:
642:
579:
76:
2689:
peptide bonds in peptides and proteins. It also bonds to and permanently disables (poisons)
4630:
4611:
4409:
4397:
4097:
3881:
3771:
3706:
3612:
1391:
1227:
978:
392:
86:
4082:
4063:
958:
146:
8:
4638:
4603:
4354:
2513:
2215:
1147:
950:
248:
136:
3885:
3775:
3710:
3616:
3200:
3169:
3117:
425:
270:
208:
4646:
4509:
4346:
3970:
3912:
3869:
3802:
3759:
3735:
3694:
2939:
2906:
2805:
1304:
660:
654:
3643:
3600:
3287:
4522:
3958:
3948:
3944:
3935:
Bornstein, Paul; Balian, Gary (1977). "Cleavage at AsnGly bonds with hydroxylamine".
3917:
3899:
3850:
3842:
3807:
3789:
3740:
3722:
3648:
3630:
3581:
3571:
3548:
3540:
3536:
3502:
3494:
3424:
3361:
3318:
3291:
3247:
3205:
3096:
3058:
2944:
2926:
2864:
2839:
2791:
2729:
2248:
2049:
1954:
1907:
1379:
1210:
1141:
170:
4035:
2721:
solutions. Hydroxylamine and its derivatives are more safely handled in the form of
2590:
4791:
4570:
4465:
4390:
4262:
4018:
3940:
3907:
3889:
3834:
3797:
3779:
3730:
3714:
3638:
3620:
3532:
3486:
3457:
3388:
3353:
3283:
3195:
3187:
3088:
3050:
2934:
2918:
2783:
2733:
2722:
2601:
2454:
2197:
2185:
2092:
2076:
1772:, a side-product insoluble in liquid ammonia, is removed by filtration; the liquid
1754:
1542:
1454:
1417:
1334:
1308:
954:
568:
498:
3490:
2736:. It may be absorbed through the skin, is harmful if swallowed, and is a possible
4753:
4555:
4453:
3996:
2892:
2nd
Edition. Reed Educational and Professional Publishing Ltd. pp. 431β432. 1997.
2381:
2335:
2175:
2061:
1859:
910:
673:
297:
3939:. Methods in Enzymology. Vol. 47(Enzyme Struct., Part E). pp. 132β45.
3601:"Localized Mutagenesis of Any Specific Small Region of the Bacterial Chromosome"
2905:
Lawton, Thomas J.; Ham, Jungwha; Sun, Tianlin; Rosenzweig, Amy C. (2014-09-01).
2787:
356:
4707:
4662:
4654:
4334:
4321:
4299:
4198:
3718:
3407:
March's advanced organic chemistry : reactions, mechanisms, and structure.
3243:
3191:
2675:
2532:). The latter can then undergo a ring-opening polymerization to yield Nylon 6.
1750:
1564:
1371:
1255:
902:
3054:
1129:
962:
898:
4817:
4670:
4533:
4517:
4488:
3903:
3846:
3793:
3726:
3634:
3585:
3544:
3498:
3295:
3092:
2930:
2671:
2578:
2484:
2465:
2400:
2385:
2312:
2088:
1911:
1891:
1470:
1451:
1383:
1355:
998:
914:
690:
557:
547:
259:
3894:
3784:
3625:
3568:
Chemical
Mutagens : Principles and Methods for Their Detection Volume 1
2551:
amine-hydroxylating agent. In is thought to mainly act via hydroxylation of
930:
4779:
4724:
4678:
4542:
4366:
4342:
4304:
3921:
3811:
3744:
3506:
3365:
3209:
2948:
2561:
2053:
1950:
1887:
1490:
1474:
1432:
41:
Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added
3868:
Caranto, Jonathan D.; Vilbert, Avery C.; Lancaster, Kyle M. (2016-12-20).
3854:
3652:
3552:
1078:
4686:
4472:
4421:
4385:
3962:
3462:
3445:
2690:
2544:
2543:
High concentrations of hydroxylamine are used by biologists to introduce
2525:
2480:
2340:
2316:
1903:
1327:
1091:
1006:
966:
3838:
3392:
2498:
1064:
970:
938:
894:
4294:
3224:
The
Systematic Identification of Organic Compounds: A Laboratory Manual
3081:
Ritz, Josef; Fuchs, Hugo; Perryman, Howard G. (2000). "Hydroxylamine".
2922:
2754:
2682:
2654:
2605:
2548:
2474:
1638:
1071:
516:
279:
239:
20:
4022:
990:
4767:
4497:
4440:
4280:
4186:
3357:
2900:
2898:
2835:
2706:
2360:
in place of the hydroxyl or amine hydrogen are (respectively) called
2256:
1958:
1863:
1550:
1205:
886:
1254:
Except where otherwise noted, data are given for materials in their
4775:
4461:
4272:
4156:
4133:
4102:
2617:
2609:
2552:
2139:
2100:
2072:
1613:
1494:
1481:
1478:
1315:
1312:
1037:
317:
2895:
1386:. It was first prepared in pure form in 1891 by the Dutch chemist
1030:
169:
4797:
4785:
4761:
4428:
4373:
4316:
4289:
4267:
4257:
4172:
4148:
2737:
2686:
2517:
2458:
2421:
2407:
1895:
1806:
1782:
1773:
1602:
1539:
1421:
1346:
1338:
1330:
1195:
906:
852:
537:
343:
2697:
of photosynthesis on account of its similar structure to water.
1776:
is evaporated to give the desired product. The net reaction is:
1390:
and by the French chemist LΓ©on
Maurice Crismer (1858-1944). The
4098:
Deadly detonation of hydroxylamine at Concept Sciences facility
3692:
3146:
2658:
2613:
2512:
Approximately 95% of hydroxylamine is used in the synthesis of
2201:
2155:
2143:
2096:
1321:
922:
219:
3990:
Japan Science and Technology Agency Failure Knowledge Database
860:
4249:
4244:
4236:
4206:
3934:
3222:
Ralph Lloyd Shriner, Reynold C. Fuson, and Daniel Y. Curtin,
2749:
2469:
2425:
2147:
1581:
1546:
1342:
1200:
986:
367:
199:
159:
3270:
Iwata, Yusaku; Koseki, Hiroshi; Hosoya, Fumio (2003-01-01).
3150:
Process of preparing hydroxylamine hydrochloride (US2242477)
2681:
Hydroxylamine can also be used to highly selectively cleave
562:
58 Β°C (136 Β°F; 331 K) /22 mm Hg (decomposes)
409:
4803:
3476:
3174:
fixation by water radical cations under ambient conditions"
2710:
2372:‑hydroxylamines are more common. Examples are
308:
3135:
manufacture of chemicals by electrolysis hydroxylamine 32.
1022:
1014:
844:
4056:
Walters, Michael A. and Andrew B. Hoem. "Hydroxylamine."
3824:
3419:
Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012).
2570:
2502:
Conversion of cyclohexanone to caprolactam involving the
1375:
1333:. Hydroxylamine is almost always provided and used as an
864:
3757:
3522:
3272:"Study on decomposition of hydroxylamine/water solution"
872:
836:
3867:
1949:
Hydroxylamine can also be produced by the reduction of
856:
4008:
3423:(2nd ed.). Oxford University Press. p. 958.
3122:(1st ed.). New York: D. Van Nostrand Co. p.
2904:
3343:
2858:
3446:"Ring-Opening PolymerizationβAn Introductory Review"
3418:
3276:
Journal of Loss Prevention in the Process Industries
2700:
2520:. The treatment of this oxime with acid induces the
848:
4083:
Calorimetric studies of hydroxylamine decomposition
3379:Hamer, Jan; Macaluso, Anthony (1964) . "Nitrones".
1830:A base then frees the hydroxylamine from the salt:
3314:Bretherick's Handbook of Reactive Chemical Hazards
3160:
840:
4058:e-Encyclopedia of Reagents for Organic Synthesis.
3269:
3080:
2911:Proteins: Structure, Function, and Bioinformatics
2823:
2821:
2693:. It is used as an irreversible inhibitor of the
2651:(HAO) further oxidizes hydroxylamine to nitrite.
187:
19:"Aminol" redirects here. Not to be confused with
4815:
832:
355:
3874:Proceedings of the National Academy of Sciences
3764:Proceedings of the National Academy of Sciences
3605:Proceedings of the National Academy of Sciences
2602:alternative industrial synthesis of paracetamol
1337:. It is consumed almost exclusively to produce
1053:
1010:
145:
3559:
3444:Nuyken, Oskar; Pask, Stephen (25 April 2013).
3166:
3084:Ullmann's Encyclopedia of Industrial Chemistry
2818:
2636:In biological nitrification, the oxidation of
2380:‑butylhydroxylamine or the
1026:
4118:
3518:
3516:
3378:
3226:, 5th ed. (New York: Wiley, 1964), chapter 6.
3025:"PrΓ©paration de l'hydroxylamine cristallisΓ©e"
2810:: CS1 maint: DOI inactive as of April 2024 (
994:
3975:: CS1 maint: multiple names: authors list (
3412:
3235:
3119:The Manufacture of Chemicals by Electrolysis
3044:
3027:(Preparation of crystalized hydroxylamine),
2861:Chemical Risk Analysis: A Practical Handbook
2767:
1002:
2416:‑organylhydroxylamines,
4125:
4111:
3668:"Hydroxylamine Mutagenesis of plasmid DNA"
3565:
3513:
3443:
3147:Osswald, Philipp; Geisler, Walter (1941).
3115:
3076:
3074:
3008:Recueil des travaux chimiques des Pays-Bas
2713:salts accelerate the decomposition of 50%
2071:A direct production of hydroxylamine from
974:
424:
269:
247:
3911:
3893:
3801:
3783:
3734:
3642:
3624:
3470:
3461:
3437:
3199:
2938:
2368:‑hydroxylamines. In general
1354:to hydroxylamine is a step in biological
391:
3598:
3592:
3029:Bulletin de la SociΓ©tΓ© chimique de Paris
2589:
2581:capsids, & mutation of purified DNA
2497:
2339:
2255:When heated, hydroxylamine explodes. A
648:Tricoordinated at N, dicoordinated at O
3599:Hong, J.-S.; Ames, B. N. (1971-12-01).
3570:. Boston, MA: Springer US. p. 41.
3071:
2884:
2882:
2880:
1326:. The compound is in a form of a white
420:
333:
4816:
2863:. ButterworthβHeinemann. p. 362.
1572:at 0 Β°C to yield a hydroxylamido-
1110:265 Β°C (509 Β°F; 538 K)
1096:129 Β°C (264 Β°F; 402 K)
260:
4106:
3307:
3305:
3265:
3263:
2831:CRC Handbook of Chemistry and Physics
1457:, hydroxylammonium hydrogen sulfate (
452:Key: AVXURJPOCDRRFD-UHFFFAOYSA-N
227:
207:
51:Ball-and-stick model of hydroxylamine
4132:
3665:
2877:
2827:
2643:to hydroxylamine is mediated by the
2326:contributes to the high reactivity.
1438:
1366:Hydroxylamine was first prepared as
552:33 Β°C (91 Β°F; 306 K)
542:1.21 g cm (at 20 Β°C)
3674:. University of Southern California
3236:Wiberg, Egon; Wiberg, Nils (2001).
2397:‑Dimethylhydroxylamine
2329:
1749:can be collected by treatment with
1420:(salts containing hydroxylammonium
462:Key: AVXURJPOCDRRFD-UHFFFAOYAD
346:
316:
13:
4064:Schupf Computational Chemistry Lab
4045:
3302:
3260:
2535:
1521:
1484:in the presence of sulfuric acid.
1049:
46:
36:
14:
4865:
4076:
2834:(87th ed.). Boca Raton, FL:
2701:Safety and environmental concerns
2095:, which can attach to either the
3405:Smith, Michael and Jerry March.
2859:Martel, B.; Cassidy, K. (2004).
1882:
1262:
802:
797:
792:
787:
782:
91:Hydroxylamine (only preselected)
62:
4029:
4002:
3983:
3928:
3861:
3818:
3751:
3686:
3659:
3409:New York. Wiley. p. 1554. 2001.
3399:
3372:
3337:
3229:
3216:
3140:
3109:
2670:, can convert hydroxylamine to
2631:
1258:(at 25 Β°C , 100 kPa).
3566:Hollaender, Alexander (1971).
3038:
3017:
2996:
2973: : 551-553. From p. 551:
2955:
2852:
2780:The Royal Society of Chemistry
1890:discovered that hydroxylamine
1370:in 1865 by the German chemist
1160:Related hydroxylammonium salts
1:
3491:10.1016/j.tplants.2005.12.007
3288:10.1016/S0950-4230(02)00072-4
3049:. Vol. 9. pp. 2β3.
2760:
1411:
532:Vivid white, opaque crystals
3945:10.1016/0076-6879(77)47016-2
3537:10.1016/0022-2836(82)90060-2
3525:Journal of Molecular Biology
3002:C. A. Lobry de Bruyn (1891)
2828:Lide, David R., ed. (2006).
2649:Hydroxylamine oxidoreductase
2448:
2082:
7:
3531:(2). Elsevier BV: 197β209.
3116:James Hale, Arthur (1919).
3004:"Sur l'hydroxylamine libre"
2975:"Ich schlage vor, dieselbe
2788:10.1039/9781849733069-FP001
2743:
2612:involves the conversion of
2058:hydroxylamine hydrochloride
1118:or concentration (LD, LC):
32:
10:
4870:
4088:Chemical company BASF info
3719:10.1038/s41467-021-27043-8
3192:10.1038/s41467-024-45832-9
3170:"Efficient catalyst-free N
2890:Chemistry of the Elements.
2663:ammonia-oxidizing bacteria
2356:Hydroxylamine derivatives
2333:
2087:Hydroxylamine reacts with
1450:is mainly produced as its
1361:
449:InChI=1S/H3NO/c1-2/h2H,1H2
18:
4752:
4591:
4333:
4229:
4141:
3485:(2). Elsevier BV: 71β79.
3055:10.1002/9780470132401.ch2
3006:(On free hydroxylamine),
2963:"Ueber das Hydroxylamine"
2728:It is an irritant to the
2477:a precursor hydroxylamine
2461:. Other methods include:
2424:group, can be reduced to
1898:salts can be produced by
1368:hydroxylammonium chloride
1252:
1168:Hydroxylammonium chloride
1153:
1114:
763:
758:
683:
635:
491:
471:
459:InChI=1/H3NO/c1-2/h2H,1H2
436:
129:
97:
85:
75:
70:
61:
31:
3093:10.1002/14356007.a13_527
2888:Greenwood and Earnshaw.
2732:, skin, eyes, and other
2705:Hydroxylamine can be an
2439:RβNHβOH (Zn, HCl) β RβNH
1643:hydroxylammonium sulfate
1374:(1838-1906); he reacted
1178:Hydroxylammonium sulfate
1173:Hydroxylammonium nitrate
881:Precautionary statements
3937:Enzyme Structure Part E
3895:10.1073/pnas.1611051113
3785:10.1073/pnas.1905873116
3626:10.1073/pnas.68.12.3158
3479:Trends in Plant Science
3346:Chemical Communications
3087:. Weinheim: Wiley-VCH.
2790:(inactive 2024-04-26).
2695:oxygen-evolving complex
2691:heme-containing enzymes
2491:
4839:Photographic chemicals
2985:(I propose to call it
2967:Zeitschrift fΓΌr Chemie
2595:
2522:Beckmann rearrangement
2507:
2504:Beckmann rearrangement
2353:
1900:electrolytic reduction
1372:Wilhelm Clemens Lossen
1223:-Dimethylhydroxylamine
1060:
52:
42:
3699:Nature Communications
3179:Nature Communications
3156:. U.S. Patent Office.
2782:. 2014. p. 993.
2645:ammonia monooxygenase
2593:
2501:
2453:Amine oxidation with
2352:-hydroxylamine schema
2343:
2200:are also employed as
1416:Hydroxylamine or its
1235:-Diethylhydroxylamine
1059:
643:Coordination geometry
50:
40:
3463:10.3390/polym5020361
3246:. pp. 675β677.
2965:(On hydroxylamine),
2961:W. C. Lossen (1865)
2667:Nitrosomonas europea
2620:with hydroxylamine.
2075:is also possible in
1392:coordination complex
1042:(fire diamond)
87:Preferred IUPAC name
3886:2016PNAS..11314704C
3880:(51): 14704β14709.
3839:10.1021/bi00087a016
3776:2019PNAS..11613293K
3770:(27): 13293β13298.
3711:2021NatCo..12.6675L
3617:1971PNAS...68.3158H
3393:10.1021/cr60230a006
3239:Inorganic Chemistry
3047:Inorganic Syntheses
2547:by acting as a DNA
2514:cyclohexanone oxime
2216:chlorosulfonic acid
2066:the hydroxamic acid
1637:This anion is then
1382:in the presence of
569:Solubility in water
524: gΒ·mol
28:
4011:J. Chem. Eng. Data
3995:2007-12-20 at the
3023:L. Crismer (1891)
2923:10.1002/prot.24535
2596:
2508:
2399:is a precursor to
2354:
2073:molecular nitrogen
2052:disproportionates
2045:(100 Β°C, 1 h)
1305:inorganic compound
1285:Infobox references
1154:Related compounds
1061:
661:Trigonal pyramidal
53:
43:
26:
16:Inorganic compound
4854:Nitrogen oxoacids
4824:Functional groups
4811:
4810:
4070:Organic Syntheses
4023:10.1021/je030121p
3954:978-0-12-181947-7
3833:(36): 9370β9378.
3666:Forsberg, Susan.
3611:(12): 3158β3162.
3577:978-1-4615-8968-6
3430:978-0-19-927029-3
3421:Organic chemistry
3253:978-0-12-352651-9
2870:978-1-903996-65-2
2797:978-0-85404-182-4
2730:respiratory tract
2516:, a precursor to
2125:OH β RβNHβOH + HX
2093:alkylating agents
2050:Hydrochloric acid
1955:potassium nitrite
1526:Another route to
1439:From nitric oxide
1380:hydrochloric acid
1293:Chemical compound
1291:
1290:
1211:Hydrogen peroxide
1188:Related compounds
1142:Safety data sheet
827:Hazard statements
727:236.18 J/(KΒ·mol)
405:CompTox Dashboard
171:Interactive image
57:
56:
4861:
4829:Inorganic amines
4801:
4789:
4765:
4754:Oxidation states
4583:
4582:
4551:
4550:
4485:
4484:
4449:
4448:
4437:
4436:
4382:
4381:
4127:
4120:
4113:
4104:
4103:
4039:
4033:
4027:
4026:
4017:(5): 1164β1169.
4006:
4000:
3987:
3981:
3980:
3974:
3966:
3932:
3926:
3925:
3915:
3897:
3865:
3859:
3858:
3822:
3816:
3815:
3805:
3787:
3755:
3749:
3748:
3738:
3690:
3684:
3683:
3681:
3679:
3663:
3657:
3656:
3646:
3628:
3596:
3590:
3589:
3563:
3557:
3556:
3520:
3511:
3510:
3474:
3468:
3467:
3465:
3441:
3435:
3434:
3416:
3410:
3403:
3397:
3396:
3381:Chemical Reviews
3376:
3370:
3369:
3358:10.1039/b923742a
3341:
3335:
3334:
3332:
3331:
3309:
3300:
3299:
3267:
3258:
3257:
3233:
3227:
3220:
3214:
3213:
3203:
3186:(1) 1535: 1535.
3164:
3158:
3157:
3155:
3144:
3138:
3137:
3132:
3130:
3113:
3107:
3106:
3078:
3069:
3068:
3042:
3036:
3035: : 793-795.
3021:
3015:
3014: : 100-112.
3000:
2994:
2959:
2953:
2952:
2942:
2917:(9): 2263β2267.
2902:
2893:
2886:
2875:
2874:
2856:
2850:
2849:
2825:
2816:
2815:
2809:
2801:
2774:"Front Matter".
2771:
2734:mucous membranes
2720:
2642:
2575:nitrosoguanidine
2455:benzoyl peroxide
2444:
2433:
2420:, where R is an
2419:
2330:Functional group
2325:
2307:
2281:
2251:
2213:
2198:dimethylglyoxime
2183:
2137:
2130:The reaction of
2126:
2117:
2044:
2043:
2042:
2039:
2026:
2025:
2022:
2014:
2013:
2012:
2009:
2004:
2003:
2000:
1987:
1986:
1983:
1978:
1977:
1974:
1945:
1921:
1878:
1826:
1815:
1814:
1811:
1791:
1790:
1787:
1771:
1755:Ammonium sulfate
1748:
1737:
1736:
1735:
1732:
1711:
1710:
1707:
1699:
1698:
1697:
1694:
1689:
1688:
1685:
1672:
1671:
1668:
1658:
1633:
1628:
1627:
1624:
1570:
1561:
1560:
1559:
1556:
1543:ammonium nitrite
1533:
1517:
1468:
1449:
1430:
1407:
1352:
1335:aqueous solution
1325:
1309:chemical formula
1275:
1269:
1266:
1265:
1081:
1074:
1067:
1052:
1032:
1028:
1024:
1020:
1016:
1012:
1008:
1004:
1000:
996:
992:
988:
984:
980:
976:
972:
968:
964:
960:
956:
952:
948:
944:
940:
936:
932:
928:
924:
920:
916:
912:
908:
904:
900:
896:
892:
888:
874:
870:
866:
862:
858:
854:
850:
846:
842:
838:
834:
806:
801:
796:
791:
786:
750:
723:
703:46.47 J/(KΒ·mol)
699:
684:Thermochemistry
612:
523:
510:
499:Chemical formula
429:
428:
413:
411:
395:
359:
348:
337:
320:
298:Gmelin Reference
281:
273:
262:
251:
231:
211:
191:
173:
149:
66:
33:
29:
25:
4869:
4868:
4864:
4863:
4862:
4860:
4859:
4858:
4849:Reducing agents
4814:
4813:
4812:
4807:
4795:
4783:
4759:
4748:
4744:
4736:
4728:
4720:
4711:
4703:
4699:
4690:
4682:
4674:
4666:
4658:
4650:
4642:
4634:
4624:
4615:
4607:
4587:
4581:
4578:
4577:
4576:
4574:
4567:
4563:
4559:
4549:
4546:
4545:
4544:
4537:
4530:
4526:
4513:
4505:
4501:
4492:
4483:
4480:
4479:
4478:
4476:
4469:
4457:
4447:
4444:
4443:
4442:
4435:
4432:
4431:
4430:
4425:
4417:
4413:
4405:
4401:
4394:
4380:
4377:
4376:
4375:
4370:
4362:
4358:
4350:
4329:
4325:
4312:
4308:
4284:
4276:
4253:
4240:
4225:
4219:
4210:
4202:
4194:
4190:
4181:
4168:
4160:
4152:
4137:
4131:
4079:
4048:
4046:Further reading
4043:
4042:
4034:
4030:
4007:
4003:
3997:Wayback Machine
3988:
3984:
3968:
3967:
3955:
3933:
3929:
3866:
3862:
3823:
3819:
3756:
3752:
3691:
3687:
3677:
3675:
3664:
3660:
3597:
3593:
3578:
3564:
3560:
3521:
3514:
3475:
3471:
3442:
3438:
3431:
3417:
3413:
3404:
3400:
3377:
3373:
3342:
3338:
3329:
3327:
3325:
3311:
3310:
3303:
3268:
3261:
3254:
3234:
3230:
3221:
3217:
3173:
3165:
3161:
3153:
3145:
3141:
3128:
3126:
3114:
3110:
3103:
3079:
3072:
3065:
3043:
3039:
3022:
3018:
3001:
2997:
2960:
2956:
2903:
2896:
2887:
2878:
2871:
2857:
2853:
2846:
2826:
2819:
2803:
2802:
2798:
2773:
2772:
2768:
2763:
2746:
2718:
2714:
2703:
2641:
2637:
2634:
2538:
2536:Laboratory uses
2494:
2483:pyrolysis (the
2451:
2442:
2438:
2432:
2428:
2417:
2382:glycosidic bond
2338:
2336:Hydroxamic acid
2332:
2323:
2319:
2305:
2301:
2297:
2293:
2289:
2279:
2275:
2271:
2267:
2263:
2246:
2242:
2238:
2234:
2230:
2211:
2207:
2196:Oximes such as
2181:
2173:
2167:
2159:
2154:
2135:
2131:
2124:
2120:
2115:
2111:
2107:
2085:
2062:carbon monoxide
2040:
2037:
2036:
2034:
2030:
2023:
2020:
2019:
2017:
2010:
2007:
2006:
2001:
1998:
1997:
1995:
1991:
1984:
1981:
1980:
1975:
1972:
1971:
1969:
1965:
1943:
1939:
1935:
1931:
1927:
1920:
1916:
1912:
1885:
1875:
1871:
1867:
1857:
1853:
1849:
1845:
1839:
1834:
1824:
1820:
1812:
1809:
1808:
1804:
1800:
1796:
1788:
1785:
1784:
1780:
1770:
1766:
1762:
1758:
1746:
1742:
1733:
1730:
1729:
1727:
1723:
1719:
1715:
1708:
1705:
1704:
1702:
1695:
1692:
1691:
1686:
1683:
1682:
1680:
1676:
1669:
1666:
1665:
1663:
1657:
1653:
1649:
1645:
1632:
1625:
1622:
1621:
1617:
1611:
1606:
1600:
1596:
1592:
1588:
1569:
1565:
1557:
1554:
1553:
1551:
1536:Raschig process
1531:
1527:
1524:
1522:Raschig process
1515:
1511:
1507:
1503:
1498:
1488:
1466:
1462:
1458:
1447:
1443:
1441:
1428:
1424:
1414:
1406:
1402:
1398:
1394:
1364:
1351:
1347:
1320:
1311:
1299:(also known as
1294:
1287:
1282:
1281:
1280: ?)
1271:
1267:
1263:
1259:
1248:
1189:
1182:
1161:
1133:
1127:
1107:
1104:
1086:
1085:
1084:
1083:
1076:
1069:
1062:
1058:
1050:
883:
829:
815:
779:
751:
748:
742:
738:
735:
734:Std enthalpy of
724:
721:
714:
711:
700:
693:
676:
657:
655:Molecular shape
645:
627:
610:
606:
601:
571:
521:
508:
504:
501:
487:
484:
479:
478:
467:
464:
463:
460:
454:
453:
450:
444:
443:
432:
414:
407:
398:
378:
362:
349:
323:
300:
291:
254:
234:
214:
194:
176:
163:
152:
139:
125:
124:
93:
92:
81:
24:
17:
12:
11:
5:
4867:
4857:
4856:
4851:
4846:
4841:
4836:
4834:Hydroxylamines
4831:
4826:
4809:
4808:
4758:
4756:
4750:
4749:
4747:
4746:
4742:
4738:
4734:
4730:
4726:
4722:
4718:
4714:
4709:
4705:
4701:
4697:
4693:
4688:
4684:
4680:
4676:
4672:
4668:
4664:
4660:
4656:
4652:
4648:
4644:
4640:
4636:
4632:
4628:
4622:
4617:
4613:
4609:
4605:
4601:
4595:
4593:
4589:
4588:
4586:
4585:
4579:
4572:
4565:
4561:
4557:
4553:
4547:
4540:
4535:
4528:
4524:
4520:
4511:
4507:
4503:
4499:
4495:
4490:
4481:
4474:
4467:
4459:
4455:
4451:
4445:
4433:
4423:
4419:
4415:
4411:
4407:
4403:
4399:
4392:
4388:
4378:
4368:
4364:
4360:
4356:
4352:
4348:
4339:
4337:
4331:
4330:
4328:
4327:
4323:
4319:
4314:
4310:
4306:
4302:
4297:
4292:
4287:
4282:
4278:
4274:
4270:
4265:
4260:
4255:
4251:
4247:
4242:
4238:
4233:
4231:
4227:
4226:
4224:
4223:
4217:
4212:
4208:
4204:
4200:
4196:
4192:
4188:
4184:
4179:
4175:
4170:
4166:
4162:
4158:
4154:
4150:
4145:
4143:
4139:
4138:
4130:
4129:
4122:
4115:
4107:
4101:
4100:
4095:
4090:
4085:
4078:
4077:External links
4075:
4074:
4073:
4066:
4061:
4054:
4047:
4044:
4041:
4040:
4028:
4001:
3982:
3953:
3927:
3860:
3817:
3750:
3685:
3658:
3591:
3576:
3558:
3512:
3469:
3456:(2): 361β403.
3436:
3429:
3411:
3398:
3371:
3336:
3323:
3301:
3259:
3252:
3244:Academic Press
3228:
3215:
3171:
3159:
3139:
3108:
3101:
3070:
3063:
3037:
3016:
2995:
2954:
2894:
2876:
2869:
2851:
2844:
2817:
2796:
2765:
2764:
2762:
2759:
2758:
2757:
2752:
2745:
2742:
2716:
2702:
2699:
2676:greenhouse gas
2639:
2633:
2630:
2598:
2597:
2537:
2534:
2510:
2509:
2493:
2490:
2489:
2488:
2478:
2472:
2450:
2447:
2446:
2445:
2440:
2430:
2401:Weinreb amides
2331:
2328:
2321:
2309:
2308:
2303:
2299:
2295:
2291:
2283:
2282:
2277:
2273:
2269:
2265:
2253:
2252:
2244:
2240:
2236:
2232:
2224:-sulfonic acid
2220:hydroxylamine-
2209:
2190:
2189:
2179:
2171:
2165:
2157:
2133:
2128:
2127:
2122:
2118:
2113:
2109:
2084:
2081:
2047:
2046:
2032:
2028:
2015:
1996:O β NH(OH)(OSO
1993:
1989:
1967:
1947:
1946:
1941:
1937:
1933:
1929:
1923:respectively:
1918:
1914:
1884:
1881:
1880:
1879:
1873:
1869:
1865:
1855:
1851:
1847:
1843:
1837:
1828:
1827:
1822:
1818:
1802:
1798:
1794:
1768:
1764:
1760:
1751:liquid ammonia
1744:
1739:
1738:
1725:
1721:
1717:
1713:
1700:
1678:
1674:
1655:
1651:
1647:
1635:
1634:
1630:
1615:
1609:
1604:
1598:
1594:
1590:
1567:
1529:
1523:
1520:
1519:
1518:
1513:
1509:
1505:
1501:
1496:
1464:
1460:
1445:
1440:
1437:
1426:
1413:
1410:
1404:
1400:
1396:
1388:Lobry de Bruyn
1363:
1360:
1349:
1318:
1301:hydroxyammonia
1292:
1289:
1288:
1283:
1261:
1260:
1256:standard state
1253:
1250:
1249:
1247:
1246:
1244:-sulfonic acid
1240:Hydroxylamine-
1237:
1225:
1213:
1208:
1203:
1198:
1192:
1190:
1187:
1184:
1183:
1181:
1180:
1175:
1170:
1164:
1162:
1159:
1156:
1155:
1151:
1150:
1145:
1138:
1137:
1134:
1125:
1123:
1120:
1119:
1112:
1111:
1108:
1101:
1098:
1097:
1094:
1088:
1087:
1077:
1070:
1063:
1048:
1047:
1046:
1045:
1043:
1034:
1033:
947:P305+P351+P338
884:
879:
876:
875:
830:
825:
822:
821:
816:
811:
808:
807:
780:
775:
772:
771:
761:
760:
756:
755:
752:
746:
740:
732:
729:
728:
725:
719:
708:
705:
704:
701:
689:
686:
685:
681:
680:
677:
672:
669:
668:
658:
653:
650:
649:
646:
641:
638:
637:
633:
632:
629:
625:
615:
614:
608:
603:
599:
589:
588:
585:
576:
575:
572:
567:
564:
563:
560:
554:
553:
550:
544:
543:
540:
534:
533:
530:
526:
525:
519:
513:
512:
506:
502:
497:
494:
493:
489:
488:
486:
485:
482:
474:
473:
472:
469:
468:
466:
465:
461:
458:
457:
455:
451:
448:
447:
439:
438:
437:
434:
433:
431:
430:
417:
415:
403:
400:
399:
397:
396:
388:
386:
380:
379:
377:
376:
372:
370:
364:
363:
361:
360:
352:
350:
342:
339:
338:
331:
325:
324:
322:
321:
313:
311:
305:
304:
301:
296:
293:
292:
290:
289:
285:
283:
275:
274:
264:
256:
255:
253:
252:
244:
242:
236:
235:
233:
232:
224:
222:
216:
215:
213:
212:
204:
202:
196:
195:
193:
192:
184:
182:
178:
177:
175:
174:
166:
164:
157:
154:
153:
151:
150:
142:
140:
135:
132:
131:
127:
126:
123:
122:
121:Nitrinous acid
119:
116:
113:
110:
109:Hydroxyammonia
107:
104:
100:
99:
95:
94:
90:
89:
83:
82:
79:
73:
72:
68:
67:
59:
58:
55:
54:
44:
27:Hydroxylamine
15:
9:
6:
4:
3:
2:
4866:
4855:
4852:
4850:
4847:
4845:
4842:
4840:
4837:
4835:
4832:
4830:
4827:
4825:
4822:
4821:
4819:
4805:
4800:
4799:
4793:
4788:
4787:
4781:
4777:
4773:
4769:
4764:
4763:
4757:
4755:
4751:
4745:
4739:
4737:
4731:
4729:
4723:
4721:
4715:
4713:
4706:
4704:
4694:
4692:
4685:
4683:
4677:
4675:
4669:
4667:
4661:
4659:
4653:
4651:
4645:
4643:
4637:
4635:
4629:
4626:
4625:
4618:
4616:
4610:
4608:
4602:
4600:
4597:
4596:
4594:
4590:
4584:
4568:
4554:
4552:
4541:
4539:
4531:
4521:
4519:
4515:
4508:
4506:
4496:
4494:
4486:
4470:
4463:
4460:
4458:
4452:
4450:
4438:
4426:
4420:
4418:
4408:
4406:
4395:
4389:
4387:
4383:
4371:
4365:
4363:
4353:
4351:
4344:
4341:
4340:
4338:
4336:
4332:
4326:
4320:
4318:
4315:
4313:
4303:
4301:
4298:
4296:
4293:
4291:
4288:
4286:
4279:
4277:
4271:
4269:
4266:
4264:
4261:
4259:
4256:
4254:
4248:
4246:
4243:
4241:
4235:
4234:
4232:
4228:
4221:
4220:
4213:
4211:
4205:
4203:
4197:
4195:
4185:
4183:
4176:
4174:
4171:
4169:
4163:
4161:
4155:
4153:
4147:
4146:
4144:
4140:
4135:
4128:
4123:
4121:
4116:
4114:
4109:
4108:
4105:
4099:
4096:
4094:
4091:
4089:
4086:
4084:
4081:
4080:
4071:
4067:
4065:
4062:
4059:
4055:
4053:
4052:Hydroxylamine
4050:
4049:
4038:Sigma-Aldrich
4037:
4032:
4024:
4020:
4016:
4012:
4005:
3998:
3994:
3991:
3986:
3978:
3972:
3964:
3960:
3956:
3950:
3946:
3942:
3938:
3931:
3923:
3919:
3914:
3909:
3905:
3901:
3896:
3891:
3887:
3883:
3879:
3875:
3871:
3864:
3856:
3852:
3848:
3844:
3840:
3836:
3832:
3828:
3821:
3813:
3809:
3804:
3799:
3795:
3791:
3786:
3781:
3777:
3773:
3769:
3765:
3761:
3754:
3746:
3742:
3737:
3732:
3728:
3724:
3720:
3716:
3712:
3708:
3704:
3700:
3696:
3689:
3673:
3669:
3662:
3654:
3650:
3645:
3640:
3636:
3632:
3627:
3622:
3618:
3614:
3610:
3606:
3602:
3595:
3587:
3583:
3579:
3573:
3569:
3562:
3554:
3550:
3546:
3542:
3538:
3534:
3530:
3526:
3519:
3517:
3508:
3504:
3500:
3496:
3492:
3488:
3484:
3480:
3473:
3464:
3459:
3455:
3451:
3447:
3440:
3432:
3426:
3422:
3415:
3408:
3402:
3394:
3390:
3386:
3382:
3375:
3367:
3363:
3359:
3355:
3352:(8): 1302β4.
3351:
3347:
3340:
3326:
3324:9780081009710
3320:
3316:
3315:
3308:
3306:
3297:
3293:
3289:
3285:
3281:
3277:
3273:
3266:
3264:
3255:
3249:
3245:
3241:
3240:
3232:
3225:
3219:
3211:
3207:
3202:
3197:
3193:
3189:
3185:
3181:
3180:
3175:
3163:
3152:
3151:
3143:
3136:
3125:
3121:
3120:
3112:
3104:
3098:
3094:
3090:
3086:
3085:
3077:
3075:
3066:
3064:9780470132401
3060:
3056:
3052:
3048:
3041:
3034:
3030:
3026:
3020:
3013:
3009:
3005:
2999:
2992:
2988:
2987:hydroxylamine
2984:
2980:
2976:
2972:
2968:
2964:
2958:
2950:
2946:
2941:
2936:
2932:
2928:
2924:
2920:
2916:
2912:
2908:
2901:
2899:
2891:
2885:
2883:
2881:
2872:
2866:
2862:
2855:
2847:
2845:0-8493-0487-3
2841:
2837:
2833:
2832:
2824:
2822:
2813:
2807:
2799:
2793:
2789:
2785:
2781:
2778:. Cambridge:
2777:
2770:
2766:
2756:
2753:
2751:
2748:
2747:
2741:
2739:
2735:
2731:
2726:
2724:
2712:
2708:
2698:
2696:
2692:
2688:
2684:
2679:
2677:
2673:
2672:nitrous oxide
2669:
2668:
2664:
2661:found in the
2660:
2656:
2652:
2650:
2646:
2629:
2625:
2621:
2619:
2615:
2611:
2607:
2604:developed by
2603:
2592:
2588:
2587:
2586:
2584:
2580:
2579:bacteriophage
2576:
2572:
2568:
2563:
2558:
2554:
2550:
2546:
2541:
2533:
2531:
2527:
2523:
2519:
2515:
2505:
2500:
2496:
2495:
2486:
2485:Cope reaction
2482:
2479:
2476:
2473:
2471:
2467:
2466:Hydrogenation
2464:
2463:
2462:
2460:
2456:
2437:
2436:
2435:
2427:
2423:
2415:
2411:
2409:
2404:
2402:
2398:
2396:
2392:
2387:
2386:calicheamicin
2383:
2379:
2375:
2371:
2367:
2363:
2359:
2351:
2347:
2342:
2337:
2327:
2318:
2314:
2313:isomerisation
2288:
2287:
2286:
2262:
2261:
2260:
2258:
2250:
2229:
2228:
2227:
2225:
2223:
2217:
2205:
2203:
2199:
2194:
2187:
2177:
2169:
2161:
2153:
2152:
2151:
2149:
2145:
2141:
2119:
2106:
2105:
2104:
2102:
2098:
2094:
2090:
2089:electrophiles
2080:
2078:
2074:
2069:
2067:
2063:
2059:
2055:
2051:
2016:
1964:
1963:
1962:
1960:
1956:
1952:
1926:
1925:
1924:
1922:
1909:
1905:
1901:
1897:
1893:
1892:hydrochloride
1889:
1883:Other methods
1877:
1861:
1841:
1833:
1832:
1831:
1816:
1792:
1779:
1778:
1777:
1775:
1756:
1752:
1701:
1681:O β NH(OH)(SO
1662:
1661:
1660:
1644:
1640:
1619:
1607:
1587:
1586:
1585:
1583:
1580:-disulfonate
1579:
1575:
1571:
1562:
1548:
1544:
1541:
1537:
1499:
1492:
1487:
1486:
1485:
1483:
1480:
1476:
1472:
1471:hydrogenation
1456:
1453:
1452:sulfuric acid
1436:
1434:
1423:
1419:
1409:
1393:
1389:
1385:
1384:ethyl nitrate
1381:
1377:
1373:
1369:
1359:
1357:
1356:nitrification
1353:
1344:
1340:
1336:
1332:
1329:
1323:
1317:
1314:
1310:
1306:
1302:
1298:
1297:Hydroxylamine
1286:
1279:
1274:
1257:
1251:
1245:
1243:
1238:
1236:
1234:
1230:
1226:
1224:
1222:
1218:
1214:
1212:
1209:
1207:
1204:
1202:
1199:
1197:
1194:
1193:
1191:
1186:
1185:
1179:
1176:
1174:
1171:
1169:
1166:
1165:
1163:
1158:
1157:
1152:
1149:
1146:
1143:
1140:
1139:
1135:
1131:
1122:
1121:
1117:
1113:
1109:
1106:
1100:
1099:
1095:
1093:
1090:
1089:
1082:
1075:
1068:
1044:
1041:
1040:
1036:
1035:
885:
882:
878:
877:
831:
828:
824:
823:
820:
817:
814:
810:
809:
805:
800:
795:
790:
785:
781:
778:
774:
773:
769:
767:
762:
757:
754:β39.9 kJ/mol
753:
745:
737:
731:
730:
726:
718:
713:
707:
706:
702:
697:
692:
691:Heat capacity
688:
687:
682:
678:
675:
674:Dipole moment
671:
670:
666:
662:
659:
656:
652:
651:
647:
644:
640:
639:
634:
630:
624:
620:
617:
616:
604:
598:
594:
591:
590:
586:
584:
583:
578:
577:
573:
570:
566:
565:
561:
559:
558:Boiling point
556:
555:
551:
549:
548:Melting point
546:
545:
541:
539:
536:
535:
531:
528:
527:
520:
518:
515:
514:
503:
500:
496:
495:
490:
481:
480:
477:
470:
456:
446:
445:
442:
435:
427:
423:
422:DTXSID7041043
419:
418:
416:
406:
402:
401:
394:
390:
389:
387:
385:
382:
381:
374:
373:
371:
369:
366:
365:
358:
354:
353:
351:
345:
341:
340:
336:
335:Hydroxylamine
332:
330:
327:
326:
319:
315:
314:
312:
310:
307:
306:
302:
299:
295:
294:
287:
286:
284:
282:
277:
276:
272:
268:
265:
263:
261:ECHA InfoCard
258:
257:
250:
246:
245:
243:
241:
238:
237:
230:
229:ChEMBL1191361
226:
225:
223:
221:
218:
217:
210:
206:
205:
203:
201:
198:
197:
190:
186:
185:
183:
180:
179:
172:
168:
167:
165:
161:
156:
155:
148:
144:
143:
141:
138:
134:
133:
128:
120:
118:Hydroxylazane
117:
114:
111:
108:
105:
102:
101:
96:
88:
84:
78:
74:
69:
65:
60:
49:
45:
39:
35:
34:
30:
22:
4844:Rocket fuels
4802:(a strongly
4796:
4784:
4771:
4760:
4620:
4215:
4177:
4069:
4057:
4031:
4014:
4010:
4004:
3985:
3936:
3930:
3877:
3873:
3863:
3830:
3827:Biochemistry
3826:
3820:
3767:
3763:
3753:
3702:
3698:
3688:
3676:. Retrieved
3671:
3661:
3608:
3604:
3594:
3567:
3561:
3528:
3524:
3482:
3478:
3472:
3453:
3449:
3439:
3420:
3414:
3406:
3401:
3384:
3380:
3374:
3349:
3345:
3339:
3328:. Retrieved
3313:
3282:(1): 41β53.
3279:
3275:
3238:
3231:
3223:
3218:
3183:
3177:
3162:
3149:
3142:
3134:
3127:. Retrieved
3118:
3111:
3082:
3046:
3040:
3032:
3031:, series 3,
3028:
3019:
3011:
3007:
2998:
2990:
2986:
2982:
2978:
2977:Hydroxylamin
2974:
2970:
2966:
2957:
2914:
2910:
2889:
2860:
2854:
2829:
2775:
2769:
2727:
2704:
2680:
2665:
2653:
2635:
2632:Biochemistry
2626:
2622:
2599:
2582:
2562:Ernst Freese
2556:
2542:
2539:
2529:
2511:
2452:
2413:
2412:
2405:
2394:
2390:
2377:
2373:
2369:
2365:
2361:
2355:
2349:
2345:
2310:
2284:
2254:
2221:
2214:reacts with
2206:
2195:
2191:
2146:produces an
2129:
2086:
2077:water plasma
2070:
2054:nitromethane
2048:
2031:O] β [NH
1951:nitrous acid
1948:
1888:Julius Tafel
1886:
1829:
1740:
1636:
1577:
1573:
1525:
1475:nitric oxide
1442:
1433:biochemistry
1415:
1365:
1300:
1296:
1295:
1241:
1232:
1228:
1220:
1216:
1115:
1103:Autoignition
1038:
818:
765:
743:
716:
695:
622:
596:
581:
368:RTECS number
130:Identifiers
115:Hydroxyazane
112:Hydroxyamine
98:Other names
80:Azinous acid
3705:(1): 6675.
2983:zu nennen."
2981:Oxyammoniak
2683:asparaginyl
2674:, a potent
2526:caprolactam
2481:Amine oxide
2358:substituted
2317:amine oxide
2112:OH β RβOβNH
1979:β N(OH)(OSO
1904:nitric acid
1817:+ 6 [NH
1716:O β [NH
1703:2 NH(OH)(SO
1512:OH][HSO
1508:β 2 [NH
1463:OH][HSO
1328:hygroscopic
1130:median dose
1116:Lethal dose
1105:temperature
1092:Flash point
813:Signal word
529:Appearance
492:Properties
267:100.029.327
209:CHEBI:15429
4818:Categories
3678:9 December
3387:(4): 476.
3330:2023-08-28
3102:3527306730
2991:oxyammonia
2761:References
2755:Amino acid
2655:Cytochrome
2549:nucleobase
2475:Alkylating
2344:Secondary
2334:See also:
2091:, such as
2027:) + [H
2018:NH(OH)(OSO
1639:hydrolyzed
1620:+ N(OH)(SO
1469:), by the
1412:Production
777:Pictograms
679:0.67553 D
636:Structure
517:Molar mass
393:2FP81O2L9Z
240:ChemSpider
158:3D model (
137:CAS Number
77:IUPAC name
21:hemiaminal
3971:cite book
3904:0027-8424
3847:0006-2960
3794:0027-8424
3727:2041-1723
3635:0027-8424
3586:851813793
3545:0022-2836
3499:1360-1385
3296:0950-4230
2931:1097-0134
2836:CRC Press
2806:cite book
2707:explosive
2657:P460, an
2545:mutations
2449:Synthesis
2257:detonator
2188:solution)
2174:C=NβOH +
2083:Reactions
2035:OH] + HSO
1959:bisulfite
1482:catalysts
1343:oxidation
1307:with the
1206:Hydrazine
1148:ICSC 0661
1019:P403+P233
983:P333+P313
979:P332+P313
951:P308+P313
943:P304+P340
939:P302+P352
935:P301+P312
768:labelling
736:formation
710:Std molar
375:NC2975000
288:232-259-2
280:EC Number
147:7803-49-8
4569: /
4532: /
4516: /
4487: /
4471: /
4464: /
4439: /
4427: /
4396: /
4384: /
4372: /
4345: /
4245:>C=NR
4142:Hydrides
4134:Nitrogen
3993:Archived
3922:27856762
3812:31209050
3745:34795260
3672:PombeNet
3507:16406304
3450:Polymers
3366:20449284
3210:38378822
3201:10879522
2949:24523098
2744:See also
2618:ketoxime
2610:Celanese
2583:in vitro
2557:in vitro
2553:cytidine
2524:to give
2408:nitrones
2376:‑
2311:Partial
2243:βOβS(=O)
2235:βCl + NH
2231:HOβS(=O)
2218:to give
2140:aldehyde
2138:with an
2121:RβX + NH
2108:RβX + NH
2101:nitrogen
1940:OH + 2 H
1842:+ NaO(CH
1821:] + 2 NH
1801:O + 6 NH
1664:N(OH)(SO
1641:to give
1597:] + 2 SO
1593:][NO
1479:platinum
1331:crystals
1303:) is an
1039:NFPA 704
759:Hazards
619:Basicity
574:Soluble
4592:Halides
4230:Organic
4136:species
3913:5187719
3882:Bibcode
3855:8369308
3803:6613137
3772:Bibcode
3736:8602370
3707:Bibcode
3653:4943557
3613:Bibcode
3553:7042980
2940:4133332
2738:mutagen
2687:glycine
2647:(AMO).
2606:Hoechst
2518:Nylon 6
2459:nitrone
2422:organyl
2418:RβNHβOH
2315:to the
2239:OH β NH
2202:ligands
2164:[NH
2103:atoms:
2099:or the
2005:) + HSO
1970:+ 2 HSO
1896:sulfate
1836:[NH
1774:ammonia
1759:[NH
1712:) + 2 H
1690:) + HSO
1646:[NH
1614:[NH
1589:[NH
1547:reduced
1540:aqueous
1534:is the
1459:[NH
1425:[NH
1422:cations
1362:History
1339:Nylon-6
1278:what is
1276: (
1196:Ammonia
712:entropy
607:[NH
593:Acidity
587:β0.758
538:Density
511:
344:PubChem
4806:oxide)
4804:acidic
4335:Oxides
3963:927171
3961:
3951:
3920:
3910:
3902:
3853:
3845:
3810:
3800:
3792:
3743:
3733:
3725:
3651:
3644:389612
3641:
3633:
3584:
3574:
3551:
3543:
3505:
3497:
3427:
3364:
3321:
3294:
3250:
3208:
3198:
3129:5 June
3099:
3061:
2947:
2937:
2929:
2867:
2842:
2794:
2659:enzyme
2614:ketone
2468:of an
2426:amines
2294:OH β N
2268:OH + O
2247:βOH +
2144:ketone
2097:oxygen
1793:+ 4 SO
1741:Solid
1612:O β 2
1341:. The
1273:verify
1270:
1144:(SDS)
819:Danger
663:at N,
605:6.03 (
522:33.030
476:SMILES
318:C00192
220:ChEMBL
189:B01184
181:3DMet
106:Azanol
103:Aminol
71:Names
4774:, 0,
4466:(HON)
4250:-CONR
4060:2001.
3154:(PDF)
2979:oder
2750:Amine
2723:salts
2616:to a
2573:, or
2470:oxime
2443:+ ZnO
2364:- or
2302:+ 3 H
2276:+ 6 H
2272:β 2 N
2168:OH]Cl
2148:oxime
1957:with
1932:+ 3 H
1906:with
1858:OH +
1840:OH]Cl
1797:+ 6 H
1582:anion
1500:+ 2 H
1477:over
1418:salts
1201:Water
667:at O
631:7.97
441:InChI
200:ChEBI
160:JSmol
4733:NHBr
4725:NHCl
4518:ONOO
4347:(NO)
4300:HNCS
4295:HNCO
4290:HOCN
4273:(CN)
4093:MSDS
4036:MSDS
3977:link
3959:PMID
3949:ISBN
3918:PMID
3900:ISSN
3851:PMID
3843:ISSN
3808:PMID
3790:ISSN
3741:PMID
3723:ISSN
3680:2021
3649:PMID
3631:ISSN
3582:OCLC
3572:ISBN
3549:PMID
3541:ISSN
3503:PMID
3495:ISSN
3425:ISBN
3362:PMID
3319:ISBN
3292:ISSN
3248:ISBN
3206:PMID
3131:2014
3097:ISBN
3059:ISBN
2945:PMID
2927:ISSN
2865:ISBN
2840:ISBN
2812:link
2792:ISBN
2711:iron
2492:Uses
2429:RβNH
2378:tert
2298:+ NH
2290:3 NH
2264:4 NH
2186:NaOH
2184:(in
2176:NaCl
2116:+ HX
2068:.
2064:via
2060:and
1936:β NH
1860:NaCl
1854:β NH
1805:β 4
1728:+ SO
1563:and
1493:+ 3
1455:salt
1395:ZnCl
1378:and
1031:P501
1027:P405
1023:P404
1015:P401
1011:P391
1007:P390
1003:P380
999:P373
995:P372
991:P363
987:P362
975:P330
971:P322
967:P321
963:P314
959:P312
955:P310
931:P281
927:P280
923:P273
919:P272
915:P271
911:P270
907:P264
903:P261
899:P260
895:P234
891:P202
887:P201
873:H400
869:H373
865:H351
861:H335
857:H318
853:H317
849:H315
845:H312
841:H302
837:H290
833:H200
665:bent
580:log
384:UNII
329:MeSH
309:KEGG
303:478
4794:,
4741:NHI
4717:NHF
4671:BrN
4663:ClN
4639:NBr
4631:NCl
4627:(?)
4538:NOO
4502:NNO
4462:HNO
4422:HNO
4398:(NO
4367:HNO
4322:-NO
4317:-NO
4285:NCN
4263:HCN
4258:-CN
4222:(?)
4019:doi
3941:doi
3908:PMC
3890:doi
3878:113
3835:doi
3798:PMC
3780:doi
3768:116
3731:PMC
3715:doi
3639:PMC
3621:doi
3533:doi
3529:154
3487:doi
3458:doi
3389:doi
3354:doi
3284:doi
3196:PMC
3188:doi
3089:doi
3051:doi
2989:or
2935:PMC
2919:doi
2784:doi
2600:An
2571:ENU
2567:EMS
2384:in
2324:NβO
2249:HCl
2178:+ H
2170:β R
2160:C=O
2142:or
2056:to
1992:+ H
1966:HNO
1953:or
1928:HNO
1910:or
1908:HCl
1902:of
1894:or
1868:(CH
1720:OH]
1677:+ H
1650:OH]
1608:+ H
1552:HSO
1549:by
1545:is
1473:of
1429:OH]
1403:OH)
1399:(NH
1376:tin
1345:of
766:GHS
747:298
720:298
611:OH]
410:EPA
357:787
347:CID
249:766
4820::
4798:+5
4792:+4
4790:,
4786:+3
4782:,
4780:+2
4778:,
4776:+1
4772:β1
4770:,
4768:β2
4766:,
4762:β3
4712:Cl
4708:NH
4687:NH
4679:IN
4655:FN
4647:NI
4621:NF
4612:NF
4604:NF
4599:NF
4543:NO
4527:NO
4523:HO
4514:NO
4510:HO
4454:NO
4441:NO
4429:NO
4391:NO
4386:NO
4374:NO
4343:NO
4305:CH
4268:CN
4237:NR
4216:NH
4199:HN
4182:OH
4178:NH
4165:NH
4157:NH
4149:NH
4015:48
4013:.
3973:}}
3969:{{
3957:.
3947:.
3916:.
3906:.
3898:.
3888:.
3876:.
3872:.
3849:.
3841:.
3831:32
3829:.
3806:.
3796:.
3788:.
3778:.
3766:.
3762:.
3739:.
3729:.
3721:.
3713:.
3703:12
3701:.
3697:.
3670:.
3647:.
3637:.
3629:.
3619:.
3609:68
3607:.
3603:.
3580:.
3547:.
3539:.
3527:.
3515:^
3501:.
3493:.
3483:11
3481:.
3452:.
3448:.
3385:64
3383:.
3360:.
3350:46
3348:.
3317:.
3304:^
3290:.
3280:16
3278:.
3274:.
3262:^
3242:.
3204:.
3194:.
3184:15
3182:.
3176:.
3133:.
3124:32
3095:.
3073:^
3057:.
3012:10
3010:,
2993:.)
2969:,
2943:.
2933:.
2925:.
2915:82
2913:.
2909:.
2897:^
2879:^
2838:.
2820:^
2808:}}
2804:{{
2740:.
2725:.
2719:OH
2715:NH
2678:.
2638:NH
2585:.
2569:,
2434::
2410:.
2403:.
2388:.
2226::
2212:OH
2208:NH
2204:.
2162:+
2150:.
2136:OH
2132:NH
2079:.
1961::
1917:SO
1876:OH
1864:CH
1862:+
1850:CH
1825:OH
1810:2β
1807:SO
1783:NO
1781:2
1767:SO
1757:,
1753:.
1747:OH
1743:NH
1731:2β
1724:SO
1659::
1654:SO
1603:NH
1601:+
1584::
1566:SO
1538::
1532:OH
1528:NH
1504:SO
1491:NO
1489:2
1448:OH
1444:NH
1435:.
1358:.
1348:NH
1126:50
1124:LD
1029:,
1025:,
1021:,
1017:,
1013:,
1009:,
1005:,
1001:,
997:,
993:,
989:,
985:,
981:,
977:,
973:,
969:,
965:,
961:,
957:,
953:,
949:,
945:,
941:,
937:,
933:,
929:,
925:,
921:,
917:,
913:,
909:,
905:,
901:,
897:,
893:,
889:,
871:,
867:,
863:,
859:,
855:,
851:,
847:,
843:,
839:,
835:,
770::
739:(Ξ
628:)
621:(p
613:)
602:)
595:(p
509:OH
505:NH
483:NO
4743:2
4735:2
4727:2
4719:2
4710:2
4702:2
4700:F
4698:2
4696:N
4691:F
4689:2
4681:3
4673:3
4665:3
4657:3
4649:3
4641:3
4633:3
4623:5
4614:3
4606:2
4580:3
4575:O
4573:2
4571:N
4566:4
4564:O
4562:2
4560:N
4558:4
4556:H
4548:4
4536:2
4534:O
4529:2
4525:2
4512:2
4504:2
4500:2
4498:H
4493:O
4491:2
4489:N
4482:2
4477:O
4475:2
4473:N
4468:2
4456:3
4446:2
4434:3
4424:3
4416:5
4414:O
4412:2
4410:N
4404:2
4402:)
4400:2
4393:2
4379:2
4369:2
4361:3
4359:O
4357:2
4355:N
4349:2
4324:2
4311:2
4309:N
4307:2
4283:2
4281:H
4275:2
4252:2
4239:3
4218:5
4209:3
4207:N
4201:3
4193:4
4191:H
4189:2
4187:N
4180:2
4173:N
4167:2
4159:4
4151:3
4126:e
4119:t
4112:v
4025:.
4021::
3999:.
3979:)
3965:.
3943::
3924:.
3892::
3884::
3857:.
3837::
3814:.
3782::
3774::
3747:.
3717::
3709::
3682:.
3655:.
3623::
3615::
3588:.
3555:.
3535::
3509:.
3489::
3466:.
3460::
3454:5
3433:.
3395:.
3391::
3368:.
3356::
3333:.
3298:.
3286::
3256:.
3212:.
3190::
3172:2
3105:.
3091::
3067:.
3053::
3033:6
2971:8
2951:.
2921::
2873:.
2848:.
2814:)
2800:.
2786::
2717:2
2685:-
2640:3
2608:β
2530:3
2528:(
2506:.
2487:)
2441:2
2431:2
2414:N
2395:O
2393:,
2391:N
2374:N
2370:N
2366:N
2362:O
2350:N
2348:,
2346:N
2322:3
2320:H
2306:O
2304:2
2300:3
2296:2
2292:2
2280:O
2278:2
2274:2
2270:2
2266:2
2245:2
2241:2
2237:2
2233:2
2222:O
2210:2
2182:O
2180:2
2172:2
2166:3
2158:2
2156:R
2134:2
2123:2
2114:2
2110:2
2041:4
2038:β
2033:3
2029:3
2024:2
2021:β
2011:4
2008:β
2002:2
1999:β
1994:2
1990:2
1988:)
1985:2
1982:β
1976:3
1973:β
1968:2
1944:O
1942:2
1938:2
1934:2
1930:3
1919:4
1915:2
1913:H
1874:3
1872:)
1870:2
1866:3
1856:2
1852:3
1848:3
1846:)
1844:2
1838:3
1823:2
1819:4
1813:4
1803:3
1799:2
1795:2
1789:2
1786:β
1769:4
1765:2
1763:]
1761:4
1745:2
1734:4
1726:4
1722:2
1718:3
1714:2
1709:3
1706:β
1696:4
1693:β
1687:3
1684:β
1679:2
1675:2
1673:)
1670:3
1667:β
1656:4
1652:2
1648:3
1631:2
1629:)
1626:3
1623:β
1618:]
1616:4
1610:2
1605:3
1599:2
1595:2
1591:4
1578:N
1576:,
1574:N
1568:2
1558:3
1555:β
1530:2
1516:]
1514:4
1510:3
1506:4
1502:2
1497:2
1495:H
1467:]
1465:4
1461:3
1446:2
1427:3
1405:2
1401:2
1397:2
1350:3
1324:H
1322:O
1319:2
1316:H
1313:N
1268:N
1242:O
1233:N
1231:,
1229:N
1221:O
1219:,
1217:N
1132:)
1128:(
1080:3
1073:1
1066:2
749:)
744:H
741:f
722:)
717:S
715:(
698:)
696:C
694:(
626:b
623:K
609:3
600:a
597:K
582:P
507:2
412:)
408:(
162:)
23:.
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