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Revision as of 14:57, 21 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 455934086 of page Hydroxylamine for the Chem/Drugbox validation project (updated: 'ChEMBL').		Latest revision as of 01:00, 17 December 2024 edit Arthurfragoso (talk | contribs)Extended confirmed users2,123 edits Fixes images on dark mode
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			{{Short description|Inorganic compound}}
	{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
			{{Redirect-distinguish|Aminol|hemiaminal}}
	{{Chembox		{{Chembox
	| Verifiedfields = changed		| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 398741254		| verifiedrevid = 461773624
	| ImageFileL1 = Hydroxylamine-2D.png		| ImageFileL1 = Hydroxylamine-2D.png
			| ImageClassL1 = skin-invert
	| ImageFileL1_Ref = {{chemboximage|correct|??}}
			| ImageFileL1_Ref = {{chemboximage|correct|??}}
	| ImageSizeL1 = 121
	| ImageNameL1 = Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added		| ImageNameL1 = Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added
	| ImageFileR1 = Hydroxylamine-3D-balls.png		| ImageFileR1 = Hydroxylamine-3D-balls.png
	| ImageFileR1_Ref = {{chemboximage|correct|??}}		| ImageFileR1_Ref = {{chemboximage|correct|??}}
			| ImageNameR1 = Ball-and-stick model of hydroxylamine
	| ImageSizeR1 = 121
			| ImageFile2 = Hydroxylamine-dimensions-2D.png
	| ImageNameR1 = Spacefill model of hydroxylamine
			| ImageClass2 = skin-invert
	| ImageFile2 = Hydroxylamine-dimensions-2D.png
	| ImageFile2_Ref = {{chemboximage|correct|??}}		| ImageFile2_Ref = {{chemboximage|correct|??}}
	| ImageSize2 = 242		| ImageSize2 = 242
	| ImageName2 = Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added and assorted dimensions		| ImageName2 = Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added and assorted dimensions
			| PIN = Hydroxylamine (only preselected<ref name="IUPAC2013_993">{{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = ] | date = 2014 | location = Cambridge | page = 993 | doi = 10.1039/9781849733069-FP001 | isbn = 978-0-85404-182-4| chapter = Front Matter}}</ref>)
	| IUPACName = Hydroxylamine
			| SystematicName =
	| SystematicName = Hydroxylamine<ref>{{Cite web|title = Hydroxylamine - PubChem Public Chemical Database|url = http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=787|work = The PubChem Project|location = USA|publisher = National Center for Biotechnology Information}}</ref>
			| OtherNames = {{ubl|Aminol|Azanol|Hydroxyammonia|Hydroxyamine|Hydroxyazane|Hydroxylazane|Nitrinous acid}}
	| OtherNames = Aminol<br />
			| IUPACName = Azinous acid
	Azanol<br />
			| Section1 = {{Chembox Identifiers
	Hydroxyamine<br />
			| CASNo = 7803-49-8
	Hydroxyazane<br />
			| CASNo_Ref = {{cascite|correct|CAS}}
	Hydroxylazane<br />
			| PubChem = 787
	Nitrinous acid
			| ChemSpiderID = 766
	| Section1 = {{Chembox Identifiers
			| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| CASNo = 7803-49-8
			| EINECS = 232-259-2
	| CASNo_Ref = {{cascite|correct|CAS}}
	| PubChem = 787		| KEGG = C00192
	| PubChem_Ref = {{Pubchemcite|correct|pubchem}}		| KEGG_Ref = {{keggcite|correct|kegg}}
			| MeSHName = Hydroxylamine
	| ChemSpiderID = 766
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChEBI_Ref = {{ebicite|correct|EBI}}
	| EINECS = 232-259-2
	| KEGG = C00192
	| KEGG_Ref = {{keggcite|correct|kegg}}
	| MeSHName = Hydroxylamine
	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI = 15429		| ChEBI = 15429
	| ChEMBL = <!-- blanked - oldvalue: 1191361 -->		| ChEMBL = 1191361
	| ChEMBL_Ref = {{ebicite|changed|EBI}}		| ChEMBL_Ref = {{ebicite|changed|EBI}}
	| RTECS = NC2975000		| RTECS = NC2975000
	| Gmelin = 478		| Gmelin = 478
	| 3DMet = B01184		| 3DMet = B01184
	| UNII_Ref = {{fdacite|changed|FDA}}		| UNII_Ref = {{fdacite|correct|FDA}}
	| UNII = 2FP81O2L9Z		| UNII = 2FP81O2L9Z
	| SMILES = NO		| SMILES = NO
			| StdInChI = 1S/H3NO/c1-2/h2H,1H2
	| SMILES1 = ON
			| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/H3NO/c1-2/h2H,1H2
			| InChI = 1/H3NO/c1-2/h2H,1H2
	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
			| StdInChIKey = AVXURJPOCDRRFD-UHFFFAOYSA-N
	| InChI = 1/H3NO/c1-2/h2H,1H2
			| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = AVXURJPOCDRRFD-UHFFFAOYSA-N
			| InChIKey = AVXURJPOCDRRFD-UHFFFAOYAD
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| InChIKey = AVXURJPOCDRRFD-UHFFFAOYAD
	}}		}}
	| Section2 = {{Chembox Properties		| Section2 = {{Chembox Properties
			| Formula = {{chem2|NH2OH}}
	| H = 3
	| N = 1		| N=1|H=3|O=1
			| Appearance = Vivid white, opaque crystals
	| O = 1
			| Density = 1.21&nbsp;g&nbsp;cm<sup>−3</sup> (at 20&nbsp;°C)<ref name="RubberBible87th">{{RubberBible87th}}</ref>
	| ExactMass = 33.021463723 g mol<sup>-1</sup>
			| MeltingPtC = 33
	| Appearance = Vivid white, opaque crystals
			| BoilingPtC = 58
	| Density = 1.21 g cm<sup>-3</sup> (at 20 °C)<ref name="RubberBible87th">{{RubberBible87th}}</ref>
			| BoilingPt_notes = /22 mm Hg (decomposes)
	| MeltingPtC = 33
	| BoilingPtC = 58		| LogP = −0.758
			| pKa = 6.03 ({{chem2|+}})
	| Boiling_notes = decomposes
	| LogP = -0.758		| pKb = 7.97
	| pKa = 13.7		| Solubility = Soluble
	| pKb = 0.3
	}}		}}
	| Section3 = {{Chembox Structure		| Section3 = {{Chembox Structure
	| Coordination = Trigonal at N		| Coordination = Tricoordinated at N, dicoordinated at O
	| MolShape = Tetrahedral at N		| MolShape = ] at N, ] at O
	| Dipole = 0.67553 D		| Dipole = 0.67553 D
	}}		}}
	| Section4 = {{Chembox Thermochemistry		| Section4 = {{Chembox Thermochemistry
	| DeltaHf = -39.9 kJ mol<sup>-1</sup>		| DeltaHf = −39.9 kJ/mol
	| Entropy = 236.18 J K<sup>-1</sup> mol<sup>-1</sup>		| Entropy = 236.18 J/(K·mol)
	| HeatCapacity = 46.47 J K<sup>-1</sup> mol<sup>-1</sup>		| HeatCapacity = 46.47 J/(K·mol)
	}}		}}
	| Section5 = {{Chembox Hazards		| Section7 = {{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
			| GHSPictograms = {{GHS01}}{{GHS05}}{{GHS07}}{{GHS08}}{{GHS09}}
	| EUIndex = 612-122-00-7
			| GHSSignalWord = Danger
	| EUClass = E {{Hazchem Xn}} {{Hazchem Xi}} {{Hazchem N}}
			| HPhrases = {{H-phrases|200|290|302|312|315|317|318|335|351|373|400}}
	| RPhrases = {{R2}}, {{R21/22}}, {{R37/38}}, {{R40}}, {{R41}}, {{R43}}, {{R48/22}}, {{R50}}
			| PPhrases = {{P-phrases|201|202|234|260|261|264|270|271|272|273|280|281|301+312|302+352|304+340|305+351+338|308+313|310|312|314|321|322|330|332+313|333+313|362|363|372|373|380|390|391|401|403+233|404|405|501}}
	| SPhrases = {{S2}}, {{S26}}, {{S36/37/39}}, {{S61}}
	| NFPA-H = 2		| NFPA-H = 2
	| NFPA-F = 1		| NFPA-F = 1
	| NFPA-R = 3		| NFPA-R = 3
	| FlashPt = 129 °C		| FlashPtC = 129
	| Autoignition = 265 °C		| AutoignitionPtC = 265
	| LD50 = 408 mg/kg (oral, mouse); 59–70 mg/kg (intraperitoneal mouse, rat); 29 mg/kg (subcutaneous, rat)<ref>{{cite book |author=Martel, B.; Cassidy, K. |title=Chemical Risk Analysis: A Practical Handbook |publisher=Butterworth–Heinemann |year=2004 |pages=362 |isbn=1903996651}}</ref>		| LD50 = 408 mg/kg (oral, mouse); 59–70 mg/kg (intraperitoneal mouse, rat); 29 mg/kg (subcutaneous, rat)<ref>{{cite book |author1=Martel, B. |author2=Cassidy, K. |title=Chemical Risk Analysis: A Practical Handbook |publisher=Butterworth–Heinemann |year=2004 |pages=362 |isbn=978-1-903996-65-2}}</ref>
	}}
	| Section6 = {{Chembox Related
	| Function = hydroxylammonium salts
	| OtherFunctn = ]<br/>]<br/>]
	| OtherCpds = ]<br />
	]
	}}		}}
			| Section8 = {{Chembox Related
			| OtherFunction_label = hydroxylammonium salts
			| OtherFunction = {{ubl|]|]|]}}
			| OtherCompounds = {{ubl|]|]|]|]|]|]|]}}
	}}		}}
			}}
			'''Hydroxylamine''' (also known as '''hydroxyammonia''') is an ] with the ] {{chem2|NH2OH|auto=1}}. The compound is in a form of a white ] ]s.<ref name="synth">Greenwood and Earnshaw. ''Chemistry of the Elements.'' 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–432. 1997.</ref> Hydroxylamine is almost always provided and used as an ]. It is consumed almost exclusively to produce ]. The ] of ] to hydroxylamine is a step in biological ].<ref name="Structural conservation of the B su">{{cite journal|last1=Lawton|first1=Thomas J.|last2=Ham|first2=Jungwha|last3=Sun|first3=Tianlin|last4=Rosenzweig|first4=Amy C.|date=2014-09-01|title=Structural conservation of the B subunit in the ammonia monooxygenase/particulate methane monooxygenase superfamily|journal=Proteins: Structure, Function, and Bioinformatics|language=en|volume=82|issue=9|pages=2263–2267|doi=10.1002/prot.24535|issn=1097-0134|pmc=4133332|pmid=24523098}}</ref>
			==History==
			Hydroxylamine was first prepared as ] in 1865 by the German chemist ] (1838-1906); he reacted ] and ] in the presence of ].<ref>W. C. Lossen (1865) (On hydroxylamine), ''Zeitschrift für Chemie'', '''8''' : 551-553. From p. 551: ''"Ich schlage vor, dieselbe ''Hydroxylamin'' oder ''Oxyammoniak'' zu nennen."'' (I propose to call it ''hydroxylamine'' or ''oxyammonia''.)</ref> It was first prepared in pure form in 1891 by the Dutch chemist ] and by the French chemist Léon Maurice Crismer (1858-1944).<ref>C. A. Lobry de Bruyn (1891) (On free hydroxylamine), ''Recueil des travaux chimiques des Pays-Bas'', '''10''' : 100-112.</ref><ref>L. Crismer (1891) (Preparation of crystalized hydroxylamine), ''Bulletin de la Société chimique de Paris'', series 3, '''6''' : 793-795.</ref> The ] {{chem2|ZnCl2(NH2OH)2}} (zinc dichloride di(hydroxylamine)), known as Crismer's salt, releases hydroxylamine upon heating.<ref>{{cite book|doi=10.1002/9780470132401.ch2|chapter=Dichlorobis(hydroxylamine)zinc(II) (Crismer's Salt)|year=1967|volume=9|last1=Walker|first1=John E.|last2=Howell|first2=David M.|title=Inorganic Syntheses|pages=2–3|isbn=9780470132401}}</ref>
			==Production==
			Hydroxylamine or its ] (salts containing hydroxylammonium ] {{chem2|+}}) can be produced via several routes but only two are commercially viable. It is also produced naturally as discussed in a section on ].
			===From nitric oxide===
			{{chem2|NH2OH}} is mainly produced as its ] ], hydroxylammonium hydrogen sulfate ({{chem2|+−}}), by the ] of ] over ] ]s in the presence of sulfuric acid.<ref name=Ullmann>{{Ullmann |doi=10.1002/14356007.a13_527|title=Hydroxylamine|year=2000|last1=Ritz|first1=Josef|last2=Fuchs|first2=Hugo|last3=Perryman|first3=Howard G.|isbn=3527306730}}</ref>
			:{{chem2|2 ] + 3 ] + 2 H2SO4 → 2 +−}}
			===Raschig process===
			Another route to {{chem2|NH2OH}} is the ]: ] ] is ] by ] and ] at 0&nbsp;°C to yield a hydroxylamido-''N'',''N''-disulfonate ]:
			:{{chem2|+− + 2 SO2 + ] + H2O → 2 +]] + N(OH)(SO3−)2}}
			This anion is then ] to give ] {{chem2|2SO4}}:
			:{{chem2|N(OH)(SO3−)2 + H2O → NH(OH)(SO3−) + HSO4-}}
			:{{chem2|2 NH(OH)(SO3−) + 2 H2O → 2SO4 + SO4(2-)}}
			Solid {{chem2|NH2OH}} can be collected by treatment with ]. ], {{chem2|2SO4}}, a side-product insoluble in liquid ammonia, is removed by filtration; the liquid ] is evaporated to give the desired product.<ref name="synth" />
			The net reaction is:
			:{{chem2|2 ] + 4 SO2 + 6 H2O + 6 NH3 → 4 ] + 6 + + 2 NH2OH}}
			A base then frees the hydroxylamine from the salt:
			:{{chem2|Cl]] + NaO(CH2)3CH3 → NH2OH + ] + ]}}<ref name="synth" />
			===Other methods===
			] discovered that hydroxylamine ] or ] salts can be produced by ] of ] with ] or ] respectively:<ref>{{cite book|last1=James Hale|first1=Arthur|title=The Manufacture of Chemicals by Electrolysis|date=1919|publisher=D. Van Nostrand Co.|location=New York|page=|edition=1st|url=https://archive.org/details/manufacturechem00halegoog|quote=manufacture of chemicals by electrolysis hydroxylamine 32.|access-date=5 June 2014}}</ref><ref>{{cite book|author1=Osswald, Philipp |author2=Geisler, Walter|title=Process of preparing hydroxylamine hydrochloride (US2242477)|year=1941|publisher=U.S. Patent Office|url=https://docs.google.com/viewer?url=patentimages.storage.googleapis.com/pdfs/US2242477.pdf}}</ref>
			:{{chem2|HNO3 + 3 H2 → NH2OH + 2 H2O}}
			Hydroxylamine can also be produced by the reduction of ] or ] with ]:
			:{{chem2|HNO2 + 2 HSO3− → N(OH)(OSO2−)2 + H2O → NH(OH)(OSO2−) + HSO4−}}
			:{{chem2|NH(OH)(OSO2−) + + → + + HSO4−}} (100&nbsp;°C, 1 h)
			] disproportionates ] to ] and ] via ].{{cn|date=March 2024}}
			A direct lab synthesis of hydroxylamine from ] in ] was demonstrated in 2024.<ref name=XiaopingZhang_2024>{{cite journal |journal=] |volume = 15 |issue = 1 |article-number = 1535 |doi=10.1038/s41467-024-45832-9 |title=Efficient catalyst-free N<sub>2</sub> fixation by water radical cations under ambient conditions |year=2024 |first1=Xiaoping|last1=Zhang|first2=Rui|last2=Su|first3=Jingling|last3=Li|first4=Liping|last4=Huang|first5=Wenwen|last5=Yang|first6=Konstantin|last6=Chingin|first7=Roman|last7=Balabin|first8=Jingjing|last8=Wang|first9=Xinglei|last9=Zhang|first10=Weifeng|last10=Zhu|first11=Keke|last11=Huang|first12=Shouhua|last12=Feng|first13=Huanwen|last13=Chen|page = 1535 |pmid=38378822|pmc=10879522}}</ref>
			==Reactions==
			Hydroxylamine reacts with ], such as ]s, which can attach to either the ] or the ] atoms:
			:{{chem2|R\sX + NH2OH → R\sO\sNH2 + HX}}
			:{{chem2|R\sX + NH2OH → R\sNH\sOH + HX}}
			The reaction of {{chem2|NH2OH}} with an ] or ] produces an ].
			:{{chem2|] + Cl]] → R2C\dN\sOH + ] + H2O}} (in ] solution)
			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.<ref>Ralph Lloyd Shriner, Reynold C. Fuson, and Daniel Y. Curtin, ''The Systematic Identification of Organic Compounds: A Laboratory Manual'', 5th ed. (New York: Wiley, 1964), chapter 6.</ref>
			Oximes such as ] are also employed as ]s.
			{{chem2|NH2OH}} reacts with ] to give ]:<ref>{{cite book|first1 = Egon|last1 = Wiberg|first2 = Nils|last2 = Wiberg|title = Inorganic Chemistry|url=https://books.google.com/books?id=Mtth5g59dEIC&pg=PA676|year = 2001|publisher = ]|isbn = 978-0-12-352651-9|pages = 675–677}}</ref>
			:{{chem2|HO\sS(\dO)2\sCl + NH2OH → NH2\sO\sS(\dO)2\sOH + ]}}
			When heated, hydroxylamine explodes. A ] can easily explode aqueous solutions concentrated above 80% by weight, and even 50% solution might prove detonable if tested in bulk.<ref name=":0">{{Cite journal |last1=Iwata |first1=Yusaku |last2=Koseki |first2=Hiroshi |last3=Hosoya |first3=Fumio |date=2003-01-01 |title=Study on decomposition of hydroxylamine/water solution |url=https://www.sciencedirect.com/science/article/pii/S0950423002000724 |journal=Journal of Loss Prevention in the Process Industries |volume=16 |issue=1 |pages=41–53 |doi=10.1016/S0950-4230(02)00072-4 |issn=0950-4230}}</ref><ref name=":1">{{Cite book |title=Bretherick's Handbook of Reactive Chemical Hazards |url=https://www.sciencedirect.com/book/9780081009710/brethericks-handbook-of-reactive-chemical-hazards |access-date=2023-08-28 |isbn=9780081009710 |language=en}}</ref> In air, the combustion is rapid and complete:
			:{{chem2|4 NH2OH + O2 → 2 N2 + 6 H2O}}
			Absent air, pure hydroxylamine requires stronger heating and the detonation does not complete combustion:
			:{{Chem2|3 NH2OH → N2 + NH3 + 3 H2O}}
			Partial ] to the ] {{chem2|H3N+\sO−}} contributes to the high reactivity.<ref>{{cite journal| title=Ammonia oxide makes up some 20% of an aqueous solution of hydroxylamine. |journal=Chemical Communications |date=28 February 2010 |pmid=20449284 |doi=10.1039/b923742a |volume=46 |issue=8 |pages=1302–4 | last1 = Kirby | first1 = AJ | last2 = Davies | first2 = JE | last3 = Fox | first3 = DJ | last4 = Hodgson | first4 = DR | last5 = Goeta | first5 = AE | last6 = Lima | first6 = MF | last7 = Priebe | first7 = JP | last8 = Santaballa | first8 = JA | last9 = Nome | first9 = F}}</ref>
			==Functional group==
			{{See also|Hydroxamic acid}}
			]
			Hydroxylamine derivatives ] in place of the hydroxyl or amine hydrogen are (respectively) called ''O''- or ''N''{{nbh}}hydroxyl&shy;amines. In general ''N''{{nbh}}hydroxyl&shy;amines are more common. Examples are ''N''{{nbh}}''tert''{{nbh}}butyl&shy;hydroxyl&shy;amine or the ] in ]. ] is a precursor to ]s.
			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 ]s.<ref>{{cite journal|doi=10.1021/cr60230a006|first1=Jan|last1=Hamer|first2=Anthony|last2=Macaluso|title=Nitrones|orig-date=29 Feb 1964|page=476|journal=Chemical Reviews|date=1964 |volume=64 |issue=4 }}</ref>
			''N''{{nbh}}organyl&shy;hydroxyl&shy;amines, {{chem2|R\sNH\sOH}}, where R is an ] group, can be reduced to ]s {{chem2|R\sNH2}}:<ref>Smith, Michael and Jerry March. ''March's advanced organic chemistry : reactions, mechanisms, and structure.'' New York. Wiley. p. 1554. 2001.</ref>
			:{{chem2|R\sNH\sOH (Zn, HCl) → R\sNH2 + ZnO}}
			===Synthesis===
			Amine oxidation with ] is the most common method to synthesize hydroxylamines. Care must be taken to prevent over-oxidation to a ]. Other methods include:
			* ] of an ]
			* ] a precursor hydroxylamine
			* ] pyrolysis (the ])
			==Uses==
			:].]]
			Approximately 95% of hydroxylamine is used in the synthesis of ], a precursor to ].<ref name=Ullmann/> The treatment of this oxime with acid induces the ] to give ] ('''3''').<ref name="Clayden-2012">{{cite book |last1=Clayden |first1=Jonathan |last2=Greeves |first2=Nick |last3=Warren |first3=Stuart |title=Organic chemistry |date=2012 |publisher=Oxford University Press |isbn=978-0-19-927029-3 |page=958 |edition=2nd}}</ref> The latter can then undergo a ring-opening polymerization to yield Nylon 6.<ref name="Pask-2013">{{cite journal |last1=Nuyken |first1=Oskar |last2=Pask |first2=Stephen |title=Ring-Opening Polymerization—An Introductory Review |journal=Polymers |date=25 April 2013 |volume=5 |issue=2 |pages=361–403 |doi=10.3390/polym5020361|doi-access=free}}</ref>
			==Laboratory uses==
			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.
			High concentrations of hydroxylamine are used by biologists to introduce ] by acting as a DNA ] amine-hydroxylating agent.<ref name="Waugh2006">{{cite journal | last1=Waugh | first1=Robbie | last2=Leader | first2=David J. | last3=McCallum | first3=Nicola | last4=Caldwell | first4=David | title=Harvesting the potential of induced biological diversity | journal=Trends in Plant Science | publisher=Elsevier BV | volume=11 | issue=2 | year=2006 | issn=1360-1385 | doi=10.1016/j.tplants.2005.12.007 | pages=71–79| pmid=16406304}}</ref> In is thought to mainly act via hydroxylation of ] to hydroxyaminocytidine, which is misread as thymidine, thereby inducing C:G to T:A transition mutations.<ref name="Busby1982a">{{cite journal | last1=Busby | first1=Stephen | last2=Irani | first2=Meher | last3=de Crombrugghe | first3=Benoít | title=Isolation of mutant promoters in the Escherichia coli galactose operon using local mutagenesis on cloned DNA fragments | journal=Journal of Molecular Biology | publisher=Elsevier BV | volume=154 | issue=2 | year=1982 | issn=0022-2836 | doi=10.1016/0022-2836(82)90060-2 | pages=197–209| pmid=7042980}}</ref> But high concentrations or over-reaction of hydroxylamine ''in vitro'' are seemingly able to modify other regions of the DNA & lead to other types of mutations.<ref name="Busby1982a" /> 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 ] noted hydroxylamine was unable to induce reversion mutations of its C:G to T:A transition effect and even considered hydroxylamine to be the most specific mutagen known.<ref name="Hollaender1971">{{cite book | last=Hollaender | first=Alexander | title=Chemical Mutagens : Principles and Methods for Their Detection Volume 1 | publisher=Springer US | publication-place=Boston, MA | year=1971 | isbn=978-1-4615-8968-6 | oclc=851813793 | page=41}}</ref> Practically, it has been largely surpassed by more potent mutagens such as ], ], or ], but being a very small mutagenic compound with high specificity, it found some specialized uses such as mutation of DNA packed within ] capsids,<ref name="Hong1971">{{cite journal | last1=Hong | first1=J.-S. | last2=Ames | first2=B. N. | title=Localized Mutagenesis of Any Specific Small Region of the Bacterial Chromosome | journal=Proceedings of the National Academy of Sciences | volume=68 | issue=12 | date=1971-12-01 | issn=0027-8424 | doi=10.1073/pnas.68.12.3158 | pages=3158–3162| pmid=4943557 | pmc=389612 | bibcode=1971PNAS...68.3158H | doi-access=free}}</ref> and mutation of purified DNA ''in vitro''.<ref>{{cite web |last1=Forsberg |first1=Susan |title=Hydroxylamine Mutagenesis of plasmid DNA |url=http://dornsife.usc.edu/pombenet/hydroxylamine-mutagenesis/ |website=PombeNet |publisher=University of Southern California |access-date=9 December 2021}}</ref>
			:]
			An ] developed by ]–] involves the conversion of ] to a ] with hydroxylamine.
			Some non-chemical uses include removal of hair from animal hides and photographic developing solutions.<ref name="RubberBible87th"/> In the semiconductor industry, hydroxylamine is often a component in the "resist stripper", which removes photoresist after lithography.
			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.<ref>{{Cite journal |last1=Langelier |first1=Marie-France |last2=Billur |first2=Ramya |last3=Sverzhinsky |first3=Aleksandr |last4=Black |first4=Ben E. |last5=Pascal |first5=John M. |date=2021-11-18 |title=HPF1 dynamically controls the PARP1/2 balance between initiating and elongating ADP-ribose modifications |journal=Nature Communications |language=en |volume=12 |issue=1 |pages=6675 |doi=10.1038/s41467-021-27043-8 |issn=2041-1723 |pmc=8602370 |pmid=34795260|bibcode=2021NatCo..12.6675L}}</ref> Similarly, Ubiquitin molecules bound to serines or threonines residues are sensitive to hydroxylamine, but those bound to lysine (isopeptide bond) are resistant.<ref>{{Cite journal |last1=Kelsall |first1=Ian R. |last2=Zhang |first2=Jiazhen |last3=Knebel |first3=Axel |last4=Arthur |first4=J. Simon C. |last5=Cohen |first5=Philip |date=2019-07-02 |title=The E3 ligase HOIL-1 catalyses ester bond formation between ubiquitin and components of the Myddosome in mammalian cells |journal=Proceedings of the National Academy of Sciences |language=en |volume=116 |issue=27 |pages=13293–13298 |doi=10.1073/pnas.1905873116 |issn=0027-8424 |pmc=6613137 |pmid=31209050 |bibcode=2019PNAS..11613293K |doi-access=free}}</ref>
			==Biochemistry==
			In biological nitrification, the oxidation of {{chem2|NH3}} to hydroxylamine is mediated by the ] (AMO).<ref name="Structural conservation of the B su"/> ] (HAO) further oxidizes hydroxylamine to nitrite.<ref>{{cite journal|last1=Arciero|first1=David M.|last2=Hooper|first2=Alan B.|last3=Cai|first3=Mengli|last4=Timkovich|first4=Russell|date=1993-09-01|title=Evidence for the structure of the active site heme P460 in hydroxylamine oxidoreductase of Nitrosomonas|journal=Biochemistry|volume=32|issue=36|pages=9370–9378|doi=10.1021/bi00087a016|pmid=8369308|issn=0006-2960}}</ref><!-- and the ] process.-->
			] P460, an ] found in the ] '']'', can convert hydroxylamine to ], a potent ].<ref>{{cite journal|last1=Caranto|first1=Jonathan D.|last2=Vilbert|first2=Avery C.|last3=Lancaster|first3=Kyle M.|date=2016-12-20|title=Nitrosomonas europaea cytochrome P460 is a direct link between nitrification and nitrous oxide emission|journal=Proceedings of the National Academy of Sciences|language=en|volume=113|issue=51|pages=14704–14709|doi=10.1073/pnas.1611051113|issn=0027-8424|pmc=5187719|pmid=27856762|bibcode=2016PNAS..11314704C |doi-access=free}}</ref>
			Hydroxylamine can also be used to highly selectively cleave ]-] peptide bonds in peptides and proteins.<ref>{{cite book|title=Enzyme Structure Part E
			|author=Bornstein, Paul; Balian, Gary|chapter=Cleavage at AsnGly bonds with hydroxylamine |series=Methods in Enzymology|year=1977|volume=47(Enzyme Struct., Part E)|pages=132–45|doi=10.1016/0076-6879(77)47016-2 |pmid=927171|isbn=978-0-12-181947-7 }}</ref> It also bonds to and permanently disables (poisons) ]. It is used as an irreversible inhibitor of the ] of photosynthesis on account of its similar structure to water.
			==Safety and environmental concerns==
			Hydroxylamine can be an ], 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.<ref name=":0" /> <ref name=":1" /> At least two factories dealing in hydroxylamine have been destroyed since 1999 with loss of life.<ref> {{webarchive|url=https://web.archive.org/web/20071220020505/http://shippai.jst.go.jp/en/Detail?fn=0&id=CC1000050& |date=2007-12-20}}.</ref> It is known, however, that ferrous and ferric ] salts accelerate the decomposition of 50% {{chem2|NH2OH}} solutions.<ref>{{cite journal |last1=Cisneros |first1=L. O. |last2=Rogers |first2=W. J. |last3=Mannan |first3=M. S. |last4=Li |first4=X. |last5=Koseki |first5=H. |title=Effect of Iron Ion in the Thermal Decomposition of 50 mass% Hydroxylamine/Water Solutions |journal=J. Chem. Eng. Data |volume=48 |issue=5 |year=2003 |pages=1164–1169 |doi=10.1021/je030121p}}</ref> Hydroxylamine and its derivatives are more safely handled in the form of ]s.
			It is an irritant to the ], skin, eyes, and other ]. It may be absorbed through the skin, is harmful if swallowed, and is a possible ].<ref> Sigma-Aldrich</ref>
			==See also==
			*]
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			==References==
			{{Reflist}}
			==Further reading==
			* {{Dead link|date=December 2022 |bot=InternetArchiveBot |fix-attempted=yes}}
			* Walters, Michael A. and Andrew B. Hoem. "Hydroxylamine." ''e-Encyclopedia of Reagents for Organic Synthesis.'' 2001.
			*
			* M. W. Rathke A. A. Millard "Boranes in Functionalization of Olefins to Amines: 3-Pinanamine" ''Organic Syntheses'', Coll. Vol. 6, p.&nbsp;943; Vol. 58, p.&nbsp;32. (preparation of hydroxylamine-O-sulfonic acid).
			==External links==
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			{{Nitrogen compounds}}
			{{Authority control}}
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