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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.
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.
Hazard Statements: H290-H302-H312-H315-H319-H317-H351-H373
May be corrosive to metals. Harmful if swallowed. Harmful in contact with skin. Causes skin irritation. Causes serious eye irritation. May cause an allergic skin reaction. Suspected of causing cancer. May cause damage to organs through prolonged or repeated exposure.
Precautionary Statements: P273-P280h-P406
Avoid release to the environment. Wear protective gloves/clothing. Store in corrosive resistant container with a resistant inner liner.