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Hydroxylamine information


Hydroxylamine
Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added
Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added
Ball-and-stick model of hydroxylamine
Ball-and-stick model of hydroxylamine
Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added and assorted dimensions
Names
IUPAC name
Azinous acid
Preferred IUPAC name
Hydroxylamine (only preselected[1])
Other names
  • Aminol
  • Azanol
  • Hydroxyammonia
  • Hydroxyamine
  • Hydroxyazane
  • Hydroxylazane
  • Nitrinous acid
Identifiers
CAS Number
  • 7803-49-8 checkY
3D model (JSmol)
  • Interactive image
3DMet
  • B01184
ChEBI
  • CHEBI:15429 checkY
ChEMBL
  • ChEMBL1191361 ☒N
ChemSpider
  • 766 checkY
ECHA InfoCard 100.029.327 Edit this at Wikidata
EC Number
  • 232-259-2
Gmelin Reference
478
KEGG
  • C00192 checkY
MeSH Hydroxylamine
PubChem CID
  • 787
RTECS number
  • NC2975000
UNII
  • 2FP81O2L9Z checkY
CompTox Dashboard (EPA)
  • DTXSID7041043 Edit this at Wikidata
InChI
  • InChI=1S/H3NO/c1-2/h2H,1H2 checkY
    Key: AVXURJPOCDRRFD-UHFFFAOYSA-N checkY
  • InChI=1/H3NO/c1-2/h2H,1H2
    Key: AVXURJPOCDRRFD-UHFFFAOYAD
SMILES
  • NO
Properties
Chemical formula
NH2OH
Molar mass 33.030 g·mol−1
Appearance Vivid white, opaque crystals
Density 1.21 g cm−3 (at 20 °C)[2]
Melting point 33 °C (91 °F; 306 K)
Boiling point 58 °C (136 °F; 331 K) /22 mm Hg (decomposes)
Solubility in water
Soluble
log P −0.758
Acidity (pKa) 6.03 ([NH3OH]+)
Basicity (pKb) 7.97
Structure
Coordination geometry
Tricoordinated at N, dicoordinated at O
Molecular shape
Trigonal pyramidal at N, bent at O
Dipole moment
0.67553 D
Thermochemistry
Heat capacity (C)
46.47 J/(K·mol)
Std molar
entropy (S298)
236.18 J/(K·mol)
Std enthalpy of
formation fH298)
−39.9 kJ/mol
Hazards
GHS labelling:
Pictograms
GHS01: ExplosiveGHS05: CorrosiveGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word
Danger
Hazard statements
H200, H290, H302, H312, H315, H317, H318, H335, H351, H373, H400
Precautionary statements
P201, P202, P234, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P362, P363, P372, P373, P380, P390, P391, P401, P403+P233, P404, P405, P501
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
2
1
3
Flash point 129 °C (264 °F; 402 K)
Autoignition
temperature
265 °C (509 °F; 538 K)
Lethal dose or concentration (LD, LC):
LD50 (median dose)
408 mg/kg (oral, mouse); 59–70 mg/kg (intraperitoneal mouse, rat); 29 mg/kg (subcutaneous, rat)[3]
Safety data sheet (SDS) ICSC 0661
Related compounds
Related hydroxylammonium salts
  • Hydroxylammonium chloride
  • Hydroxylammonium nitrate
  • Hydroxylammonium sulfate
Related compounds
  • Ammonia
  • Water
  • Hydrazine
  • Hydrogen peroxide
  • N,O-Dimethylhydroxylamine
  • N,N-Diethylhydroxylamine
  • Hydroxylamine-O-sulfonic acid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula NH2OH. The compound is in a form of a white hygroscopic crystals.[4] Hydroxylamine is almost always provided and used as an aqueous solution. It is consumed almost exclusively to produce Nylon-6. The oxidation of NH3 to hydroxylamine is a step in biological nitrification.[5]

  1. ^ "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 993. doi:10.1039/9781849733069-FP001 (inactive 2024-04-26). ISBN 978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
  2. ^ Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN 0-8493-0487-3.
  3. ^ Martel, B.; Cassidy, K. (2004). Chemical Risk Analysis: A Practical Handbook. Butterworth–Heinemann. p. 362. ISBN 978-1-903996-65-2.
  4. ^ Greenwood and Earnshaw. Chemistry of the Elements. 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–432. 1997.
  5. ^ Lawton, Thomas J.; Ham, Jungwha; Sun, Tianlin; Rosenzweig, Amy C. (2014-09-01). "Structural conservation of the B subunit in the ammonia monooxygenase/particulate methane monooxygenase superfamily". Proteins: Structure, Function, and Bioinformatics. 82 (9): 2263–2267. doi:10.1002/prot.24535. ISSN 1097-0134. PMC 4133332. PMID 24523098.

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Hydroxylamine

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Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula NH2OH. The compound is in a form of a white hygroscopic...

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Raschig hydroxylamine process

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The Raschig process for the production of hydroxylamine is one of three chemical processes developed by German chemist Friedrich Raschig. The main step...

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Hydroxylammonium sulfate

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[NH3OH]2SO4, is the sulfuric acid salt of hydroxylamine. It is primarily used as an easily handled form of hydroxylamine, which is explosive when pure. Hydroxylammonium...

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Hydroxylamine reductase

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In enzymology, a hydroxylamine reductase (EC 1.7.99.1) is an enzyme that catalyzes the chemical reaction NH3 + H2O + acceptor ⇌ {\displaystyle \rightleftharpoons...

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Hydroxylamine dehydrogenase

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Hydroxylamine dehydrogenase (EC 1.7.2.6, HAO (ambiguous)) is an enzyme with systematic name hydroxylamine:ferricytochrome-c oxidoreductase. This enzyme...

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Hydroxylammonium chloride

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formula [NH3OH]+Cl−. It is the hydrochloric acid salt of hydroxylamine (NH2OH). Hydroxylamine is a biological intermediate in nitrification (biological...

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Hydroxylamine oxidoreductase

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Hydroxylamine oxidoreductase (HAO) is an enzyme found in the prokaryotic genus Nitrosomonas. It plays a critically important role in the biogeochemical...

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Free base

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hydrochlorides. For example, compare the free base hydroxylamine (NH2OH) with the salt hydroxylamine hydrochloride (NH3OH+ Cl−). Cocaine hydrochloride...

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Oxime

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structure R1C(=NOH)NR2R3. Oximes are usually generated by the reaction of hydroxylamine with aldehydes (R−CH=O) or ketones (RR’C=O). The term oxime dates back...

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Nitrifying bacteria

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monooxygenase (which oxidizes ammonia to hydroxylamine), hydroxylamine oxidoreductase (which oxidizes hydroxylamine to nitric oxide - which is further oxidized...

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Aspartyltransferase

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7) is an enzyme that catalyzes the chemical reaction L-asparagine + hydroxylamine ⇌{\displaystyle \rightleftharpoons } NH3 + L-aspartylhydroxamate Thus...

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Metal nitrosyl complex

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react to give [Mo(NO)2Cl2]n. Diazald is also used as an NO source. Hydroxylamine is a source of nitric oxide anion via a disproportionation: K2[Ni(CN)4]...

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KAHA Ligation

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The α-Ketoacid-Hydroxylamine (KAHA) Amide-Forming Ligation is a chemical reaction that is used to join two unprotected fragments in peptide synthesis...

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Hydroxylammonium nitrate

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nitrate or hydroxylamine nitrate (HAN) is an inorganic compound with the chemical formula [NH3OH]+[NO3]−. It is a salt derived from hydroxylamine and nitric...

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Hydroxycarbamide

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reaction of calcium cyanate with hydroxylamine nitrate in absolute ethanol and by the reaction of a cyanate salt and hydroxylamine hydrochloride in aqueous solution...

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Limonene

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bond. This species is then converted to the oxime with a base, and the hydroxylamine is removed to give the ketone-containing carvone. In nature, limonene...

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Amino radical

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The amino radical may also be produced by reaction of e−(aq) with hydroxylamine (NH2OH). Several studies also utilized the redox system of TiIII−NH2OH...

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Procainamide

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procainamide reactivates hydroxylamine and nitroso metabolites, which bind to histone proteins and are toxic to lymphocytes. The hydroxylamine and nitroso metabolites...

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Hyponitrite reductase

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hyponitrite reductase is an enzyme that catalyzes the oxidation of hydroxylamine H 2NOH by the nicotinamide adenine dinucleotide cation (NAD+) into hyponitrous...

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Drugs controlled by the UK Misuse of Drugs Act

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N-Methyl-N-(a-methyl-3,4-methylenedioxyphenethyl)hydroxylamine O-Methyl-N-(a-methyl-3,4-methylenedioxyphenethyl)hydroxylamine a-Methyl-4-(methylthio)phenethylamine...

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Cope reaction

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Cope, is the elimination reaction of an N-oxide to an alkene and a hydroxylamine. Typically, the amine oxide is prepared from the corresponding amine...

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Nitrosomonas

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{\displaystyle {\ce {NH3}}} (ammonia) to NH 2 OH {\displaystyle {\ce {NH2OH}}} (hydroxylamine). The amoCAB operon contains three different genes: amoA, amoB and amoC...

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Reduction of nitro compounds

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below) Several methods have been described for the production of aryl hydroxylamines from aryl nitro compounds: Raney nickel and hydrazine at 0-10 °C Electrolytic...

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Dimethylglyoxime

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give biacetyl monoxime. The second oxime is installed using sodium hydroxylamine monosulfonate: Dimethylglyoxime forms complexes with metals including...

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Nitrous oxide

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If the nitrite is added to the hydroxylamine solution, the only remaining by-product is salt water. If the hydroxylamine solution is added to the nitrite...

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Nitrification

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which are responsible for catalyzing the conversion of ammonia to hydroxylamine (NH2OH), a crucial intermediate in the process of nitrification. This...

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