Title: N-Bromosuccinimide
CAS Registry Number: 128-08-5
CAS Name: 1-Bromo-2,5-pyrrolidinedione
Synonyms: succinbromimide; NBS
Molecular Formula: C4H4BrNO2
Molecular Weight: 177.98
Percent Composition: C 26.99%, H 2.27%, Br 44.89%, N 7.87%, O 17.98%
Literature 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.
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.
Melting point: mp 173-175° (slight decompn)
Density: d 2.098
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.
