3,4-Xylidine

3,4-Xylidine
Names
Preferred IUPAC name
3,4-Dimethylaniline
Other names
3,4-Dimethylphenylamine
3,4-Dimethylbenzenamine
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.002.217 Edit this at Wikidata
UNII
  • InChI=1S/C8H11N/c1-6-3-4-8(9)5-7(6)2/h3-5H,9H2,1-2H3 ☒N
    Key: DOLQYFPDPKPQSS-UHFFFAOYSA-N ☒N
  • Cc1ccc(N)cc1C
Properties
C8H11N
Molar mass 121.183 g·mol−1
Melting point 51.0 °C (123.8 °F; 324.1 K)
Boiling point 226.0 °C (438.8 °F; 499.1 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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3,4-Xylidine is an organic compound with the formula C6H3(CH3)2NH2. It is one of several isomeric xylidines. It is a colorless solid. It is a precursor for the production of riboflavin (vitamin B2).[1]

The compound is prepared by two routes: hydrogenation of (2-chloromethyl)-4-nitrotoluene and reaction of the bromoxylene with ammonia.[1]

Safety

Like other xylidines, 3,4-xylidine has modest toxicity with an LD50 of 812 mg/kg when administered orally to rats.[1]

In 2003, more than twenty US Army troops were allegedly exposed to 3,4-xylidine during the occupation of Iraq, leading to a number of health complaints.[2]

References

  1. ^ a b c M. Meyer (2012). "Xylidines". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a28_455. ISBN 978-3527306732.
  2. ^ "12 Years Later, a Mystery of Chemical Exposure in Iraq Clears Slightly". New York Times. May 14, 2015.