N,N-Dimethylphenylenediamine

Chemical compound From Wikipedia, the free encyclopedia

N,N-Dimethylphenylenediamine (dimethyl-4-phenylenediamine) is an organic compound with the formula H2NC6H4N(CH3)2. It is one of the phenylenediamines, a class of compounds that have long attracted attention for their redox properties. This diamine is, for example, easily oxidized to a deep red radical cation, [H2NC6H4N(CH3)2]+ which is called Wurster's Red.[2] The related Wurster's Blue cation has four N-methyl groups (CH3)2NC6H4N(CH3)+2

Structure of Wurster's Red bromide with bond distances in picometers
Quick facts Names, Identifiers ...
N,N-Dimethylphenylenediamine
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)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.552 Edit this at Wikidata
EC Number
  • 202-807-5
KEGG
UNII
UN number 2811 (DIMETHYL-P-PHENYLENEDIAMINE)
  • InChI=1S/C8H12N2/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,9H2,1-2H3
    Key: BZORFPDSXLZWJF-UHFFFAOYSA-N
  • CN(C)C1=CC=C(C=C1)N
Properties
C8H12N2
Molar mass 136.198 g·mol−1
Appearance colorless solid
Density 1.036 g/cm³
Melting point 53 °C (127 °F; 326 K)[1]
Boiling point 262 °C (504 °F; 535 K)[1]
Hazards
GHS labelling:
GHS06: Toxic
Danger
H301, H311, H331
P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

Dimethyl-4-phenylenediamine is prepared by the nitration of dimethylaniline followed by reduction of the resulting 4-nitrodimethylaniline. A variety of methods have been examined.[3]

Applications

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

It reacts with carbon disulfide to give the corresponding mercaptobenzothiazole:

(CH3)2NC6H4NH2 + CS2 + S → (CH3)2NC6H3NCSH)S + H2S

History

Casmir Wurster discovered tetramethylphenylenediamine and its easy oxidation.[5] Subsequent work revealed the variety of redox properties of the phenylenediamines.[6]

References

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