Bronopoly

Structural formula
General
Surname	Bronopoly
other names	BNPD BNPK Bronocot Falisolan 2-bromo-2-nitropropane-1,3-diol 2-BROMO-2-NITROPROPANE-1,3-DIOL ( INCI )
Molecular formula	C 3 H 6 BrNO 4
Brief description	colorless crystals
External identifiers / databases
CAS number 52-51-7 EC number 200-143-0 ECHA InfoCard 100,000,131 PubChem 2450 ChemSpider 2356 DrugBank DB13960 Wikidata Q2462902
properties
Molar mass	199.99 g mol −1
Physical state	firmly
Melting point	130-133 ° C
solubility	Easily soluble in water (250 g l −1 at 22 ° C)
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary danger H and P phrases H: 302 + 312-315-318-335-410 P: 261-273-280-302 + 352 + 312-305 + 351 + 338 + 310-501
Toxicological data	180 mg kg −1 ( LD 50 ,  rat ,  oral ) 1600 mg kg −1 ( LD 50 ,  rabbit ,  transdermal )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Bronopol ( 2-bromo-2-nitro-1,3-propanediol ) is a chemical compound from the group of diols that has a bacteriostatic and disinfectant effect.

properties

The compound works by releasing formaldehyde , which is slow compared to other biocides. Furthermore, Bronopol has an electrophilic carbon atom that reacts with nucleophilic biomolecules and, among other things, inactivates thiols in the active centers of some enzymes . Due to both mechanisms of action, Bronopol has a broad spectrum of action and can be used from pH 5 to 9, but the effect of the electrophile can be reduced by organic substances, and the effect occurs comparatively slowly with up to 24 hours. Bronopol is particularly effective against pseudomonads . Aluminum, iron and substances with a mercapto group (-SH) reduce the activity of bronopol. Bronopol produces relatively little contact dermatitis compared to other biocides . At neutral or basic pH values, Bronopol can release nitrite , so that nitrosamines can form in the presence of amines . Bronopol is compatible with quaternary ammonium compounds and cationic biocides.

Extraction and presentation

Bronopol is obtained by bromination of di (hydroxymethyl) nitromethane , which is derived from nitromethane .

use

Bronopol was originally used as a preservative for medicines. Due to its low mammalian toxicity Bronopol has become a widely used preservative in shampoos and cosmetics developed. The minimum inhibitory concentration (MIC) is 0.0025%, in products it is used at a concentration of 0.02% to 0.1%. It is particularly effective against Pseudomonas aeruginosa .

safety

Bronopol can lead to the formation of nitrosamines .

See also

• Bronidox

Individual evidence

1. ↑ Entry on 2-BROMO-2-NITROPROPANE-1,3-DIOL in the CosIng database of the EU Commission, accessed on May 22, 2020.
2. ↑ ^{a b c d e f} Entry on 2-bromo-2-nitro-1,3-propanediol in the GESTIS substance database of the IFA , accessed on January 8, 2020(JavaScript required) .
3. ↑ Data sheet 2-Bromo-2-nitro-1,3-propanediol, 98% from Sigma-Aldrich , accessed on October 21, 2013 ( PDF ).
4. ↑ Entry on Bronopol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on August 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
5. ↑ Mustapha Kireche, Jean-Luc Peiffer, Diane Antonios, Isabelle Fabre, Elena Giménez-Arnau, Marc Pallardy, Jean-Pierre Lepoittevin, Jean-Claude Ourlin: Evidence for Chemical and Cellular Reactivities of the Formaldehyde Releaser Bronopol, Independent of Formaldehyde Release . In: Chemical Research in Toxicology . tape 24 , no. 12 , December 19, 2011, p. 2115-2128 , doi : 10.1021 / tx2002542 ( PDF ).
6. ↑ ^{a b c d e f g} W. Paulus: Microbicides for the Protection of Materials: A Handbook. Springer Science & Business Media, 2012. ISBN 9789401121187 . Pp. 70-72.
7. ↑ Sheldon B. Markofsky: Nitro Compounds, Aliphatic , p. 6 in Ullmann's Encyclopedia of Industrial Chemistry, 2012, Wiley-VCH, Weinheim, doi : 10.1002 / 14356007.a17_401.pub2 .
8. ↑ Data sheet ( Memento of the original from October 21, 2013 in the Internet Archive ) Info: The archive link was inserted automatically and has not yet been checked. Please check the original and archive link according to the instructions and then remove this notice. (PDF; 68 kB) from Schülke & Mayr .  
9. ↑ SD Gangolli, Royal Society of Chemistry (Great Britain): The Dictionary of Substances and Their Effects (DOSE): Volume 01 A-B . Royal Society of Chemistry, 1999, ISBN 0-85404-808-1 , pp. 723 ( limited preview in Google Book search).
10. ↑ SCCS: Opinion on Nitrosamines and Secondary Amines in Cosmetic Products , p. 18.