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

Methyldibromo glutaronitrile (MDBGN) is a widely used preservative.

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. 1 2 3 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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