Methyldibromo glutaronitrile

Methyldibromo glutaronitrile (MDBGN) is a widely used preservative.

Methyldibromo glutaronitrile
Structural formula of methyldibromo glutaronitrile
Names
IUPAC name
2-Bromo-2-(bromomethyl)-pentanedinitrile
Other names
1,2-Dibromo-2,4-dicyanobutane
1-Bromo-1-(bromomethyl)-1,3-propanedicarbonitrile
2-Bromo-2-(bromomethyl) glutaronitrile
2-Bromo-2-(bromomethyl)pentanedinitrile
Bromothalonil
Euxyl K400
Tektamer 38
Merquat 2200
Metacide 38
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.047.877
EC Number
  • 252-681-0
UNII
  • InChI=1S/C6H6Br2N2/c7-4-6(8,5-10)2-1-3-9/h1-2,4H2
    Key: DHVLDKHFGIVEIP-UHFFFAOYSA-N
  • InChI=1/C6H6Br2N2/c7-4-6(8,5-10)2-1-3-9/h1-2,4H2
    Key: DHVLDKHFGIVEIP-UHFFFAOYAK
  • C(CC(CBr)(C#N)Br)C#N
Properties
C6H6Br2N2
Molar mass 265.936 g·mol−1
Appearance White to yellow crystals
Melting point 51.2 to 52.5 °C (124.2 to 126.5 °F; 324.3 to 325.6 K)
Boiling point 212 °C (414 °F; 485 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

It is made by reacting bromine with 2-methyleneglutaronitrile below 30 °C. An allergy to the chemical can be discovered by performing a patch test.

History and allergy

In the mid-1980s, a maximum concentration of 0.1% in stay-on and rinse-off cosmetics was allowed.[1] It was discovered soon afterwards that it caused allergic contact dermatitis to people with eczema.[1]

It has been in use since the 1990s as a preservative in skin care products such as lotions, wet wipes, shampoo, and liquid soaps. Industrial applications include its use in preserving oils, glues, and medical gels.[2]

In 2005, the EU banned its use in stay-on products,[3] and in 2007 banned it in rinse-off products.[1]

In 2005–06, methyldibromoglutaronitrile/ phenoxyethanol was the ninth-most-prevalent allergen in patch tests (5.8%).[4]

References
  1. Ngan, Vanessa. "Allergy to methyldibromo glutaronitrile". DermNet NZ. Retrieved 21 September 2013.
  2. "Allergy to methyldibromo glutaronitrile". Dermnetnz.org. 2014-01-20. Retrieved 2014-04-09.
  3. Jeanne Duus Johansen; Peter J. Frosch; Jean-Pierre Lepoittevin (29 September 2010). Contact Dermatitis. Springer. p. 575. ISBN 978-3-642-03827-3. Retrieved 21 September 2013.
  4. Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS, Mathias CG, Deleo VA, Rietschel RL, Marks J. Patch-test results of the North American Contact Dermatitis Group 2005–2006. Dermatitis. 2009 May–Jun;20(3):149-60.
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