2-bromo-2- (bromomethyl) pentanedinitrile

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Structural formula
Structural formula of 2-bromo-2- (bromomethyl)
Simplified structural formula without stereochemistry
General
Surname 2-bromo-2- (bromomethyl) pentanedinitrile
other names
  • 2-bromo-2- (bromomethyl) pentanedinitrile
  • 1,2-dibromo-2,4-dicyanobutane
  • 2-bromo-2- (bromomethyl) glutardonitrile
  • Methyldibromoglutaronitrile
  • (±) -2-Bromo-2- (bromomethyl) pentanedinitrile
  • (±) -1,2-dibromo-2,4-dicyanobutane
  • (±) -2-Bromo-2- (bromomethyl) glutardonitrile
  • (±) -Methyldibromoglutaronitrile
  • ( RS ) -2-Bromo-2- (bromomethyl) pentanedinitrile
  • ( RS ) -1,2-dibromo-2,4-dicyanobutane
  • ( RS ) -2-bromo-2- (bromomethyl) glutardonitrile
  • ( RS ) -Methyldibromoglutaronitrile
  • MDBGN
Molecular formula C 6 H 6 Br 2 N 2
Brief description

white-yellow, crystalline powder, pungent odor

External identifiers / databases
CAS number 35691-65-7
EC number 252-681-0
ECHA InfoCard 100,047,877
PubChem 61948
ChemSpider 55806
Wikidata Q1972088
properties
Molar mass 265.93 g mol −1
Physical state

firmly

density

1.1 g cm −3

Melting point

51-55 ° C

boiling point

212 ° C

solubility
  • poorly soluble in water (3.8 g l −1 )
  • easily soluble in organic solvents
safety instructions
GHS labeling of hazardous substances
05 - Corrosive 07 - Warning 09 - Dangerous for the environment

danger

H and P phrases H: 302-315-317-318-400
P: 280-305 + 351 + 338-310
Toxicological data
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2-Bromo-2- (bromomethyl) pentanedinitrile (or methyldibromoglutaronitrile , English methyldibromo glutaronitrile ) is a 1: 1 mixture ( racemate ) of two enantiomeric chemical compounds from the group of the nitriles and the organic bromine compounds . Methyldibromoglutaronitrile is a biocide and was mostly used together with phenoxyethanol (MDBGN / PE, Euxyl K 400 ) as a preservative in cosmetics .

The compound has a broad, balanced spectrum of activity that includes bacteria , fungi and yeast .

Extraction and presentation

Methyldibromoglutaronitrile can be prepared by reacting 2-methyleneglutaronitrile with bromine in an alcoholic solvent.

regulation

Methyldibromoglutaronitrile was launched in the USA in 1980 and in Europe in 1985 and was suspected of being a contact allergen early on . In 1983 a sensitization was described for the first time . With the increasing use of the compound, the sensitization rates increased in the following years.

In 2005, it was used in stay-on products (which remain on the skin for a long time after application, such as make-up) and in 2007 in rinse-off products (which are used again after application such as shampoos) are prohibited.

Individual evidence

  1. ↑ a b c d Entry on 2-bromo-2- (bromomethyl) glutaronitrile. In: Römpp Online . Georg Thieme Verlag, accessed on November 2, 2015.
  2. ↑ a b c d e f g Entry on 2-bromo-2- (bromomethyl) pentandinitrile in the GESTIS substance database of the IFA , accessed on January 23, 2020(JavaScript required) .
  3. ↑ Data sheet methyldibromoglutaronitrile from Sigma-Aldrich , accessed on January 23, 2020 ( PDF ).
  4. ↑ a b Jeanne Duus Johansen et al .: Decreasing trends in methyldibromo glutaronitrile contact allergy - following regulatory intervention . In: Contact Dermatitis . tape 59 , no. 1 , July 1, 2008, p. 48–51 , doi : 10.1111 / j.1600-0536.2008.01364.x ( PDF ).
  5. ↑ Patent US6548692 : Method for preparing 2-bromo-2-bromomethyl-glutaronitrile. Filed April 25, 2002 , published April 15, 2003 , Applicant: ISP, Inventor: Satish C. Nigam, Cletis Stiffler. ‌
  6. ↑ Peter Wallner: Environmental medicine expertise on the substance methyldibromoglutaronitrile