Dimethyl-4-phenylenediamine

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Dimethyl-4-phenylenediamine
Names
Preferred IUPAC name
N1,N1-Dimethylbenzene-1,4-diamine
Other names
p-Aminodimethylaniline; N,N-Dimethyl-p-phenylenediamine; 4-(Dimethylamino)aniline; p-Amino-N,N-dimethylaniline; p-(Dimethylamino)aniline; DMPPDA; Dimethyl-p-phenylenediamine; 4-Amino-N,N-dimethylaniline; p-Dimethylaminophenylamine; DMPD
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.002.552 Edit this at Wikidata
UNII
  • CN(C)C1=CC=C(C=C1)N
Properties
C8H12N2
Molar mass 136.198 g·mol−1
Appearance Reddish-violet crystals[1]
Melting point 53 °C (127 °F; 326 K)[1]
Boiling point 262 °C (504 °F; 535 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dimethyl-4-phenylenediamine is an amine. It has been used as an accelerator for the vulcanization of rubber.[2] It can be used in oxidase tests.

Synthesis

Dimethyl-4-phenylenediamine is made by the nitrosylation of dimethylaniline followed by reduction.

Applications

Dimethyl-4-phenylenediamine can be converted to methylene blue by reaction with dimethylaniline and sodium thiosulfate in several steps:[3]

It is used as accelerator for the vulcanization of rubber, being first converted to the corresponding mercaptobenzothiazole.

References

  1. ^ a b c Merck Index, 11th Edition, 3242
  2. ^ Geer, W. C.; Bedford, C. W. (January 24, 1925). "The History of Organic Accelerators in the Rubber Industry". Industrial and Engineering Chemistry. 17 (4): 393–396. doi:10.1021/ie50184a021.
  3. ^ Horst Berneth (2012). "Azine Dyes". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a03_213.pub3. ISBN 9783527303854.
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