1447. Bronopol

Nomenclature

CAS number: 52-51-7
2-Bromo-2-nitro-1,3-propanediol; β-bromo-β-nitrotrimethyleneglycol; Bronosol (Green Cross).
C3H6BrNO4; mol wt 199.99.
C 18.02%, H 3.02%, Br 39.95%, N 7.00%, O 32.00%.

Description and references

Prepn: E. Schmidt, R. Wilkendorf, Ber. 52, 389 (1919); R. Wessendorf, DE 1804068; idem, DE 1954173; idem, US 3658921; idem, US 3711561 (1970, 1971, 1972, 1973 all to Henkel & Cie). Antibacterial, antifungal and toxic properties: Z. Eckstein et al., Bull. Acad. Pol. Sci. Ser. Sci. Chim. 11, 687 (1963); B. Croshaw et al., J. Pharm. Pharmacol. 16 (Suppl), 127T (1964); N. G. Clark et al., GB 1057131; eidem, US 3558788 (1967, 1971 both to Boots); R. J. Stretton, T. W. Mason, J. Appl. Bacteriol. 36, 61 (1973). Biotransformation and distribution in rats: H. S. Buttar, R. H. Downie, Toxicol. Lett. 6, 101 (1980). As a nitrosating agent for diethanolamine: I. Schmeltz, A. Wenger, Food Cosmet. Toxicol. 17, 105 (1979); R. L. Elder, J. Environ. Pathol. Toxicol. 4, 47 (1980). Review of bronopol and other preservatives: B. Croshaw, J. Soc. Cosmet. Chem. 28, 3-16 (1977).

Chemical structure

Properties

Odorless crystals from ethyl acetate-chloroform, mp 120-122°. Sol in water, alcohol, ethyl acetate. Slightly sol in chloroform, acetone, ether, benzene. Insol in ligroin. LD50 in mice, rats (mg/kg): 350, 400 orally (Croshaw).

Use

Preservative in cosmetics and toiletries. Antiseptic.