1094. Benzoin Oxime

Nomenclature

CAS number: 441-38-3
2-Hydroxy-1,2-diphenylethanone oxime; 2-hydroxy-2-phenylacetophenone oxime.
C14H13NO2; mol wt 227.26.
C 73.99%, H 5.77%, N 6.16%, O 14.08%.

Description and references

Two isomers occur: α or anti and β or syn. Both have been prepd from benzoin and hydroxylamine hydrochloride. Prepn of α-form: Werner, Detscheff, Ber. 38, 69 (1905); F. J. Welcher, Organic Analytical Reagents vol. III (Van Nostrand, New York, 1947) pp 239-251. Prepn of β-form: Werner, Detscheff, loc. cit. Configuration of α- and β-forms: Meisenheimer, Meis, Ber. 57, 289 (1924).

Chemical structure

Derivative

α-Form.

Nomenclature

Cupron (Ayerst).

Properties

Prisms from benzene, mp 151-152°. Darkens on exposure to light. Slightly sol in water; sol in alc, aq ammonium hydroxide soln. Protect from light.

Derivative

β-Form.

Properties

Prismatic crystals from ether. Ether of crystn is lost on standing in air. Ether-free compd, mp 99°.

Use

The α-form is used in the detection and determination of Cu, Mo, and W: Welcher, loc. cit.