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Sigma-Aldrich

N,N-Dimethyl-p-phenylenediamine

97%

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Synonym(s):
4-(Dimethylamino)aniline, 4-Amino-N,N-dimethylaniline, N,N-Dimethyl-1,4-phenylenediamine, DMPPDA
Linear Formula:
(CH3)2NC6H4NH2
CAS Number:
99-98-9
Molecular Weight:
136.19
Beilstein/REAXYS Number:
508105
EC Number:
202-807-5
MDL number:
MFCD00007860
UNSPSC Code:
12352100
PubChem Substance ID:
24851626
NACRES:
NA.21

Quality Level

200

assay

97%

form

solid

bp

262 °C (lit.)

mp

34-36 °C (lit.)

SMILES string

CN(C)c1ccc(N)cc1

InChI

1S/C8H12N2/c1-10(2)8-5-3-7(9)4-6-8/h3-6H,9H2,1-2H3

InChI key

BZORFPDSXLZWJF-UHFFFAOYSA-N

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General description

N,N-Dimethyl-p-phenylenediamine (DPD, DMPD) is an aromatic amine mainly used as an intermediate to produce dyes. Its oxidation reaction with H2O2 in the presence of iron(III) catalyst has been used for the spectrophotometric detection of trace quantities of iron (III). Cyclovoltammetric studies have been conducted to evaluate the electrochemical oxidation of DMPD at various pH. DMPD on oxidation under basic conditions has been reported to undergo hydrolytic decomposition.

Application

N,N-Dimethyl-p-phenylenediamine may be used for the preparation of molecular compounds with tetracyano-p-quinodimethane (TCNQ). Polarized absorption spectra of these molecular compounds were investigated.

Pictograms

Skull and crossbones
GHS06

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Danger

Hazard Classifications

Acute Tox. 1 Dermal - Acute Tox. 2 Oral - Acute Tox. 3 Inhalation

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Spectrophotometric catalytic determination of an ultratrace amount of iron (III) in water based on the oxidation of N, N-dimethyl-p-phenylenediamine by hydrogen peroxide.
Hirayama K and Unohara N.
Analytical Chemistry, 60(23), 2573-2577 (1988)
Polarized Absorption Spectra of Single Crystals of Ion Radical Salts. I. Molecular Compounds of 7, 7, 8, 8-Tetracyano-p-quinodimethane with N, N, N', N'-Tetramethyl-p-phenylenediamine and N, N-Dimethyl-p-phenylenediamine.
Kuroda H, et al.
Bulletin of the Chemical Society of Japan, 41(12), 2855-2858 (1968)
Mechanism diversity in anodic oxidation of N, N-dimethyl-p-phenylenediamine by varying pH.
Maleki A and Nematollahi D.
Journal of Electroanalytical Chemistry, 704, 75-79 (2013)
An historical review of the use of dye precursors in the formulation of commercial oxidation hair dyes.
Corbett JF.
Dyes and Pigments, 41(1), 127-136 (1999)
Francisco J Morales et al.
Journal of agricultural and food chemistry, 50(16), 4657-4661 (2002-07-26)
The Maillard reaction has a dramatic impact on the overall acceptance and nutritional quality of most of the foods consumed daily in European countries. Melanoidins are polymeric structures formed in the last stage of the Maillard reaction with nearly unknown
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