1398. N-Bromoacetamide

Nomenclature

CAS number: 79-15-2
Acetobromamide.
C2H4BrNO; mol wt 137.96.
C 17.41%, H 2.92%, Br 57.92%, N 10.15%, O 11.60%.
CH3CONHBr.

Description and references

Prepd by treating a cooled (0-5°) soln of acetamide dissolved in bromine with ice cold aq 50% KOH, allowing to stand for 2-3 hr at 0-5°, treating with NaCl, and extracting with chloroform: Oliveto, Gerold, Org. Synth. 31, 17 (1951).

Properties

Needles from chloroform + hexane, mp 102-105°. Sol in warm water, freely sol in cold ether. Unstable to light and heat.

Derivative

Monohydrate.

Properties

Rectangular plates from hydr ether, mp 70-80°. Freely sol in cold water, alcohol, ether, less freely in chloroform.

Use

Brominating agent; in oxidation of primary and secondary alcohols.