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193992

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:
508105
EC Number:
202-807-5
MDL number:
MFCD00007860
PubChem Substance ID:
24851626
NACRES:
NA.21

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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This Item
407275P23954241393
N,N-Dimethyl-p-phenylenediamine 97%

Sigma-Aldrich

193992

N,N-Dimethyl-p-phenylenediamine

N,N-Dimethylaniline purified by redistillation, ≥99.5%

Sigma-Aldrich

407275

N,N-Dimethylaniline

m-Phenylenediamine flakes, 99%

Sigma-Aldrich

P23954

m-Phenylenediamine

N-Phenyl-p-phenylenediamine 98%

Sigma-Aldrich

241393

N-Phenyl-p-phenylenediamine

form

solid

form

liquid

form

flakes

form

liquid

bp

262 °C (lit.)

bp

193-194 °C (lit.)

bp

282-284 °C

bp

-

mp

34-36 °C (lit.)

mp

1.5-2.5 °C (lit.)

mp

64-66 °C

mp

68-72 °C (lit.)

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

Signal Word

Danger

Hazard Statements

H300 + H310 - H331

Hazard Classifications

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

Storage Class Code

6.1A - Combustible, acute toxic Cat. 1 and 2 / very toxic hazardous materials

WGK

WGK 3

Flash Point(F)

195.8 °F - closed cup

Flash Point(C)

91 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Sigma-Aldrich

07672

N,N-Diethyl-p-phenylenediamine sulfate salt

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)
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)
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)
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)
Erin L Willis et al.
PloS one, 6(7), e21159-e21159 (2011-07-19)
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