Bronopol

Title: Bronopol
CAS Registry Number: 52-51-7
CAS Name: 2-Bromo-2-nitro-1,3-propanediol
Additional Names: b-bromo-b-nitrotrimethyleneglycol
Trademarks: Bronosol (Green Cross)
Molecular Formula: C3H6BrNO4
Molecular Weight: 199.99
Percent Composition: C 18.02%, H 3.02%, Br 39.95%, N 7.00%, O 32.00%
Line Formula: HOCH2CBr(NO2)CH2OH
Literature 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).
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).
Melting point: mp 120-122°
Toxicity data: LD50 in mice, rats (mg/kg): 350, 400 orally (Croshaw)
Use: Preservative in cosmetics and toiletries. Antiseptic.
Broparoestrol Bropirimine Brostallicin Brotizolam Brovincamine

Bronopol
Bronopol
Bronopol 3D ball-and-stick.png
Identifiers
CAS number 52-51-7 YesY
ChemSpider 2356 YesY
UNII 6PU1E16C9W YesY
KEGG D01577 YesY
ATCvet code QD01AE91
Jmol-3D images Image 1
Properties
Molecular formula C3H6BrNO4
Molar mass 199.989 g/mol
Appearance white
Melting point 130 °C
Boiling point 140 °C (decomposes)
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Bronopol (INN) is an organic compound that is used as an antimicrobial. It is a white solid although commercial samples appear yellow.

Bronopol was invented by The Boots Company PLC in the early 1960s and first applications were as a preservative for pharmaceuticals. Owing to its low mammalian toxicity (at in-use levels) and high activity against bacteria (especially the troublesome Gram-negative species), bronopol became popular as a preservative in many consumer products such as shampoos and cosmetics. It was subsequently adopted as an antimicrobial in other industrial environments such as paper mills, oil exploration and production facilities, as well as cooling water disinfection plants. It is used at concentrations of 0.0025% (25 parts per million).