1438. N-Bromosuccinimide

Nomenclature

CAS number: 128-08-5
1-Bromo-2,5-pyrrolidinedione; succinbromimide; NBS.
C4H4BrNO2; mol wt 177.98.
C 26.99%, H 2.27%, Br 44.89%, N 7.87%, O 17.98%.

Description and references

Prepn: K. Ziegler et al., Ann. 551, 109 (1942). In bromination of olefins: eidem, ibid. 80. The method has been extended to other classes of compds by the use of catalysts: H. Schmid, P. Karrer, Helv. Chim. Acta 29, 573 (1946); H. Schmid, ibid. 1144. In oxidation of aldehydes: Y. F. Cheung, Tetrahedron Lett. 1979, 3809. Review of uses: C. Djerassi, Chem. Rev. 43, 271-317 (1948); R. Filler, ibid. 63, 21-43 (1963); J. S. Pizey, Synthetic Reagents vol. 2 (John Wiley, New York, 1974) pp 1-63.

Chemical structure

Properties

Orthorhombic bisphenoidal crystals, mp 173-175° (slight decompn). Faint odor of bromine. d 2.098. Soly (g/100 g of solvent at 25°): water 1.47; tert-butanol 0.73; acetone 14.40; carbon tetrachloride 0.02; hexane 0.006; glacial acetic acid 3.10.

Caution

Highly irritating to eyes, skin, mucous membranes.

Use

In bromination of olefins; in oxidation of alcohols to aldehydes and ketones and of aldehydes to acid bromides.