4828. Hydroxylamine

Nomenclature

CAS number: 7803-49-8
H3NO; mol wt 33.03.
H 9.15%, N 42.41%, O 48.44%.
NH2OH.

Description and references

Prepn as the hydrochloride: W. L. Semon, Org. Synth. coll. vol. I, 318 (1932). Prepn: Hurd, Inorg. Synth. 1, 87 (1939); Benson et al., J. Am. Chem. Soc. 78, 4202 (1956). Crystal structure: Meyers, Lipscomb, Acta Crystallogr. 5, 583 (1955). Toxicity data: Riemann, Acta Pharmacol. Toxicol. 6, 285 (1950); R. P. Smith, W. R. Layne, J. Pharmacol. Exp. Ther. 165, 30 (1969). Mutagenic action: Phillips, Brown in Prog. Nucleic Acid Res. Mol. Biol. 7, 349-368 (1967). Reviews: Mason, “Hydroxylamine” in Mellor's vol. VIII, supplement 2, Nitrogen (part 2), 115-157 (1967); Jones in Comprehensive Inorganic Chemistry vol. 2, J. C. Bailar, Jr. et al., Eds. (Pergamon Press, Oxford, 1973) pp 265-276.

Properties

Unstable, large white flakes or needles, mp 33°, bp22 58°. d40 1.2255; d440 1.204. pK (20°) 7.97. Very sol in water, liquid ammonia and methanol. The soly in the higher alcohols decreases with increasing mol wt. Sparingly sol in ether, benzene, carbon disulfide, chloroform. Very hygroscopic. Dec by hot water. Undergoes rapid decompn at room temp esp in the presence of atm moisture and CO2. Detonates in test tube heated with flame. LD50 i.p. in mice: 1.83 mmol/kg (Smith, Layne).

Derivative

Hydrochloride.

Nomenclature

CAS number: 5470-11-1
Oxammonium hydrochloride.
H3NO.HCl; mol wt 69.49.
H 5.80%, N 20.16%, O 23.02%, Cl 51.02%.

Properties

Monoclinic columnar crystals; slowly dec when moist. d17 1.67. mp about 151°. One gram dissolves in about 1 ml water (83 g in 100 ml water at 17°); 19 ml alcohol; 8 ml methanol. Sol in glycerol, propylene glycol. Insol in cold ether. pH of 0.2 molar aq soln 3.2. Keep well closed. LD50 orally in mice: 408 mg/kg (Riemann).

Derivative

Sulfate.

Nomenclature

CAS number: 10039-54-0
Oxammonium sulfate.
(H3NO)2.H2SO4; mol wt 164.14.
H 4.91%, N 17.07%, O 58.48%, S 19.54%.

Properties

Crystals, mp about 170°. Freely sol in water.

Caution

Skin irritant. May cause methemoglobinemia, sulfhemoglobinemia, cyanosis, convulsions, hypotension and coma. See Clinical Toxicology of Commercial Products, R. E. Gosselin et al., Eds. (Williams & Wilkins, Baltimore, 5th ed., 1984) Section II, p 117.

Use

As reducing agent in photography. Reagent in synthetic and analytical chemistry. Purification of aldehydes and ketones. Detection of mercury and silver in water. As antioxidant for fatty acids and soaps. As dehairing agent for hides.