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Acetaldoxime is used as an oxygen scavenger in boiler water. It is also used as an intermediate in chemical synthesis and pharmaceuticals. It is involved in the rearrangement reaction to prepare acetamide by using nickel(II) acetate as a catalyst. It acts as a precursor to prepare heterocyclic compound such as spiroisoxazoline. Further, it is used to prepare alkylated(Z)-oximes by deprotonation followed by reaction with benzyl bromide.
The dimetallated species (n-BuLi, -78o) can be alkylated at the ɑ-position: Tetrahedron Lett., 25, 263 (1984).
Chlorination with NCS: Tetrahedron, 40, 2985 (1984), or chlorine, gives the chloroxime, dehydrochlorination of which generates acetonitrile N-oxide, a reactive 1,3-dipole which undergoes cycloadditions with alkenes providing a one-pot route to 2-isoxazolines (same ref.):
Nitrile oxides can be generated from other aldoximes in a similar manner. The resulting isoxazolines can readily be reduced to 3-hydroxy ketones.
Yu, J.; Jin, Y.; Lu, M. 3-Methyl-4-oxa-5-azahomoadamantane as an Organocatalyst for the Aerobic Oxidation of Primary Amines to Oximes in Water. Adv. Synth. Catal. 2015, 357 (6), 1175-1180.
Yu, J.; Cao, X.; Lu, M. A novel and efficient catalytic system including TEMPO/acetaldoxime/InCl 3 for aerobic oxidation of primary amines to oximes. Tetrahedron Lett. 2014, 55 (42), 5751-5755.
Hazard Statements: H302-H312-H332
Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled.
Precautionary Statements: P261-P264b-P270-P271-P280-P301+P312-P302+P352-P304+P340-P312-P330-P363-P501c
Avoid breathing dust/fume/gas/mist/vapours/spray. Wash face, hands and any exposed skin thoroughly after handling Do not eat, drink or smoke when using this product. Use only outdoors or in a well-ventilated area. Wear protective gloves/protective clothing/eye protection/face protection. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. IF ON SKIN: Wash with plenty of soap and water. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Rinse mouth. Wash contaminated clothing before reuse. Dispose of contents/ container to an approved waste disposal plant