Methyldibromo glutaronitrile

Methyldibromo glutaronitrile (MDBGN) is a widely used preservative.

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
CAS Number	35691-65-7 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:62823
ChemSpider	55806
ECHA InfoCard	100.047.877
EC Number	252-681-0
PubChem CID	61948
UNII	YX089CPS05 Y
CompTox Dashboard (EPA)	DTXSID3024944
InChI 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
SMILES C(CC(CBr)(C#N)Br)C#N
Properties
Chemical formula	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.

External links

• Patient information sheet