Hydroxylamine hydrochloride

• Catalog No.: A15398
• CAS Number: 5470-11-1
• M. F.: ClH4NO
• M. W.: 69.49086
• Purity: 99%

SYNONYMS

• Title: 盐酸羟胺
• IUPAC name: hydroxylamine hydrochloride
• IUPAC Traditional name: primary amine hydrochloride
• Synonyms: Hydroxylammonium chloride

DATABASE IDS

• EC Number: 226-798-2
• CAS Number: 5470-11-1
• MDL Number: MFCD00051089
• Merck Index: 144828
• Beilstein Number: 3539763

PROPERTIES

• Purity: 99%
• Density: 1.67
• Melting Point: 152°C dec.
• GHS Hazard statements: H200-H351-H373-H290-H315-H319-H400-H302-H312-H317
• European Hazard Symbols: X
• European Hazard Symbols: Explosive (E)
• European Hazard Symbols: Nature polluting (N)
• GHS Precautionary statements: P280H-P273-P406
• Risk Statements: 2-21/22-36/38-40-43-48/22-50
• RTECS: NC3675000
• Safety Statements: 36/37-61
• Storage Warning: Hygroscopic
• TSCA Listed: 是
• Hazard Class: 8
• UN Number: UN2923
• Packing Group: III

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 110-115^o, 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).