Methyldibromo glutaronitrile

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 ;
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 ;
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

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

^ ^a ^b ^c Ngan, Vanessa. "Allergy to methyldibromo glutaronitrile". DermNet NZ. Retrieved 21 September 2013.
^ "Allergy to methyldibromo glutaronitrile". Dermnetnz.org. 2014-01-20. Retrieved 2014-04-09.
^ 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.
^ 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

[NZ-1] Ngan, Vanessa. "Allergy to methyldibromo glutaronitrile". DermNet NZ. Retrieved 21 September 2013.

[dermnetnz1-2] "Allergy to methyldibromo glutaronitrile". Dermnetnz.org. 2014-01-20. Retrieved 2014-04-09.

[JohansenFrosch2010-3] 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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