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107-29-9 - Acetaldoxime, syn + anti, 98% - Acetaldehyde oxime - A10640 - Alfa Aesar

A10640 Acetaldoxime, syn + anti, 98%

CAS Number
107-29-9
Synonyms
Acetaldehyde oxime

Size Price ($) Quantity Availability
50g 31.93
250g 128.75
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Acetaldoxime, syn + anti, 98%

MDL
MFCD00002124
EINECS
203-479-6

Chemical Properties

Formula
CH3CH=NOH
Formula Weight
59.07
Boiling Point
115-117°
Flash Point
36°(96°F)
Density
0.969
Refractive Index
1.4260
Solubility
Soluble in water, ethanol and ether.

Applications

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.

Notes

Store in a cool place. Incompatible with strong oxidizing agents.

Literature References

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.

GHS Hazard and Precautionary Statements

Hazard Statements: H226-H302-H312-H332-H319

Flammable liquid and vapour. Harmful if swallowed. Harmful in contact with skin. Harmful if inhaled. Causes serious eye irritation.

Precautionary Statements: P210-P261-P280-P240-P241-P303+P361+P353-P305+P351+P338-P304+P340-P301+P312-P501a

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves/protective clothing/eye protection/face protection. Ground/bond container and receiving equipment. Use explosion-proof electrical/ventilating/lighting/ equipment. IF ON SKIN (or hair): Remove/Take off immediately all contaminated clothing. Rinse skin with water/shower. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. IF SWALLOWED: Call a POISON CENTER or doctor/physician if you feel unwell. Dispose of contents/container in accordance with local/regional/national/international regulations.

Other References

Merck
14,42
Beilstein
1209252
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2928.00
TSCA
Yes
RTECS
AB2975000

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