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5470-11-1 - Hydroxylamine hydrochloride, 99% - Hydroxylammonium chloride - A15398 - Alfa Aesar

A15398 Hydroxylamine hydrochloride, 99%

CAS Number
5470-11-1
Synonyms
Hydroxylammonium chloride

Size Price ($) Quantity Availability
100g 19.62
250g 26.06
500g 47.28
1000g 70.86
5000g 243.08
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Hydroxylamine hydrochloride, 99%

MDL
MFCD00051089
EINECS
226-798-2

Chemical Properties

Formula
H3NO•HCl
Formula Weight
69.49
Melting point
152° dec.
Density
1.67
Sensitivity
Hygroscopic
Solubility
Soluble in water, alcohol, methanol and glycerol.

Applications

Hydroxylamine hydrochloride is a monomoamine oxidase inhibitor. It is used to prepare oximes and hydroxmic acids in organic synthesis. It acts as a copolymerization inhibitor. It can be used to remove bromine and polybromide from a solution during extraction of lignin from lignocellulosic biomass. It is key starting material for the preparation of pharmaceuticals and agrochemicals. It plays a vital role in rubber and plastic industries as an antioxidant, a vulcanization accelerator and a radical scavenger. It is also used as a color stabilizer and emulsion additive in color films.

Notes

Air and moisture sensitive. Incompatible with strong oxidizing agents, phosphorous pentachloride, calcium and anhydrous copper(II) sulfate.

Literature References

For examples of preparation of oximes from carbonyl compounds, see: Org. Synth. Coll., 2, 70, 313 (1955); 7, 149 (1990). Dehydration of aldoximes is a valuable route to nitriles. The preparation of an oxime, and dehydration with acetic anhydride, are exemplified for veratraldehyde: Org. Synth. Coll., 2, 622 (1943). For other methods of dehydrating oximes to nitriles, see Benzaldoxime, A12053. Procedures for the one-pot conversion of aldehydes to nitriles, without isolation of the intermediate oxime, include: refluxing the aldehyde with hydroxylamine hydrochloride in formic acid/ sodium acetate: J. Chem. Soc., 1564 (1965); formic acid alone: Synthesis, 112 (1979); in pyridine and toluene, with azeotropic water removal: Synthesis, 190 (1982); in DMF (reflux; aromatics only): Z. Chem., 15, 302 (1975); heating in NMP at 110-115o, effective for aromatic and aliphatic substrates; under these conditions, DMF gave only 20-30% conversion: Synthesis, 586 (1999). A more recent ambient temperature one-pot procedure utilizes DBU in combination with ethyl dichlorophosphate: Synlett, 1317 (2007).

For a one-pot synthesis of pyrazoles from aldehydes by cyclization of the intermediate oxime in acidic medium with potassium dihyrogen phosphate, see: Tetrahedron Lett., 47, 43 (2006).

For a brief feature on uses of this reagent in Organic synthesis, see: Synlett, 1326 (2007).

Mahajan, S.; Sharma, B.; Kapoor, K. K. A solvent-free one step conversion of ketones to amides via Beckmann rearrangement catalysed by FeCl 3· 6H 2 O in presence of hydroxylamine hydrochloride. Tetrahedron Lett. 2015, 56 (14), 1915-1918.

Wang, W.; Zhao, X. M.; Wang, J. L.; Geng, X.; Gong, J. F.; Hao, X. Q.; Song, M. P. Transition metal-free synthesis of primary amides from aldehydes and hydroxylamine hydrochloride. Tetrahedron Lett. 2014, 55 (20), 3192-3194.

GHS Hazard and Precautionary Statements

Hazard Statements: H351-H373-H290-H315-H319-H400-H302-H312-H317

Suspected of causing cancer. May cause damage to organs through prolonged or repeated exposure. May be corrosive to metals. Causes skin irritation. Causes serious eye irritation. Very toxic to aquatic life. Harmful if swallowed. Harmful in contact with skin. May cause an allergic skin reaction.

Precautionary Statements: P273-P280h-P406

Avoid release to the environment. Wear protective gloves/clothing. Store in corrosive resistant container with a resistant inner liner.

Other References

Merck
14,4828
Beilstein
3539763
Hazard Class
8
Packing Group
III
Harmonized Tariff Code
2825.10
TSCA
Yes
RTECS
NC3675000

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