N,N-Dimethylphenylenediamine

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

CAS NumberY

3D model (JSmol)

ChemSpiderY

EC Number202-807-5

PubChem CID

UNIIN

UN number2811 (DIMETHYL-P-PHENYLENEDIAMINE)

CompTox Dashboard (EPA)

InChI InChI=1S/C8H12N2/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,9H2,1-2H3Key: BZORFPDSXLZWJF-UHFFFAOYSA-N

SMILES CN(C)C1=CC=C(C=C1)N

Properties

Chemical formulaC8H12N2

Molar mass136.198 g·mol−1

Appearancecolorless solid

Density1.036 g/cm³

Melting point53 °C (127 °F; 326 K)

Boiling point262 °C (504 °F; 535 K)

Hazards

GHS labelling:

Pictograms

Signal wordDanger

Hazard statementsH301, H311, H331

Precautionary statementsP261, 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). N verify (what is YN ?) Infobox references

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. 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

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.

Applications

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

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. Subsequent work revealed the variety of redox properties of the phenylenediamines.