3,4-Xylidine

Last updated
3,4-Xylidine
3,4-Xylidin.svg
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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C8H11N/c1-6-3-4-8(9)5-7(6)2/h3-5H,9H2,1-2H3 X mark.svgN
    Key: DOLQYFPDPKPQSS-UHFFFAOYSA-N X mark.svgN
  • 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).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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]

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<i>m</i>-Xylene Chemical compound

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<span class="mw-page-title-main">3,5-Xylidine</span> Chemical compound

3,5-Xylidine is the organic compound with the formula C6H3(CH3)2NH2. It is one of several isomeric xylidines. It is a colorless viscous liquid. It is used in the production of the dye Pigment Red 149.

<span class="mw-page-title-main">2,6-Xylidine</span> Chemical compound

2,6-Xylidine is an organic compound with the formula C6H3(CH3)2NH2. It is one of several isomeric xylidines. It is a colorless viscous liquid. Commercially significant derivatives are the anesthetics lidocaine, bupivacaine, mepivacaine, and etidocaine.

<span class="mw-page-title-main">2,5-Xylidine</span> Chemical compound

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<span class="mw-page-title-main">2,4-Xylidine</span> Chemical compound

2,4-Xylidine is an organic compound with the formula C6H3(CH3)2NH2. It is one of several isomeric xylidines. It is a colorless viscous liquid. Commercially significant derivatives include the veterinary drug cymiazole and the colorant Pigment Yellow 81.

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<i>o</i>-Anisidine Chemical compound

o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.

<i>m</i>-Anisidine Chemical compound

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<span class="mw-page-title-main">2,3-Xylidine</span> Chemical compound

2,3-Xylidine is the organic compound with the formula C6H3(CH3)2NH2. it is one of several isomeric xylidines. It is a colorless viscous liquid. The compound is used in the production of the drug mefenamic acid and the herbicide xylachlor.

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References

  1. 1 2 3 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.