Dimethylphenylenediamine

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Structural formula
Structure of dimethylphenylenediamine
General
Surname Dimethylphenylenediamine (DMPD)
other names
  • Dimethyl- p- phenylenediamine
  • N , N -dimethyl-1,4-phenylenediamine
Molecular formula C 8 H 12 N 2
Brief description

brown to black solid

External identifiers / databases
CAS number 99-98-9
EC number 202-807-5
ECHA InfoCard 100.002.552
PubChem 7472
ChemSpider 13884246
Wikidata Q409957
properties
Molar mass 136.20 g mol −1
Physical state

firmly

density

1.09 g cm −3

Melting point

35 ° C

boiling point

262 ° C

pK s value

6.59

solubility
  • poor in water (11 g l −1 at 20 ° C)
  • Easily soluble in alcohol, ether and benzene
safety instructions
GHS hazard labeling from  Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary
06 - Toxic or very toxic

danger

H and P phrases H: 300-311-331
P: 261-280-301 + 310 + 330-302 + 352-304 + 340-271
Toxicological data

30 mg kg −1 ( LD 50 ,  mouse ,  oral )

As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dimethylphenylenediamine ( DMPD ), more precisely N , N -dimethyl-1,4-phenylenediamine, is a chemical compound . It is a derivative of p -phenylenediamine .

Extraction and presentation

Dimethylphenylenediamine can be obtained by catalytic reduction of p -nitrodimethylaniline .

properties

Dimethyl- p -phenylenediamine, like all derivatives of p -phenylenediamine, forms stable, colored semiquinonediimine radical cations (Wurster red) when an electron is released . Further release of an electron and a proton produces colorless quinonediimine cations.

Oxidation of dimethylphenylenediamine

The free base is also very reactive to oxidation by atmospheric oxygen. This creates deep brown to black high molecular weight compounds. The salts are less sensitive.

use

Dimethylphenylenediamine is used as a redox indicator and detection reagent ( oxidase test ) and as an intermediate for pigment dyes.

Other names

  • Wurster red after Casimir Wurster , who used it in paper analysis to detect wood pulp.

See also

Individual evidence

  1. ↑ a b c d e f g Entry on N, N-dimethyl-p-phenylenediamine in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
  2. ↑ a b Entry on N, N-dimethyl-p-benzenediamine in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on July 31, 2018 or earlier.
  3. ↑ a b c Toxicological assessment of N, N-dimethyl-p-phenylenediamine (PDF) at the professional association for raw materials and chemical industry (BG RCI), accessed on August 22, 2012.
  4. ↑ Entry on 4-amino-N, N-dimethylaniline in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), accessed on February 1, 2016. Manufacturers or distributors can expand the harmonized classification and labeling .
  5. ↑ U. Nickel: Reactions with Wurster's cations , in: Chemistry in our time 12, 1978, pp. 89-98; doi : 10.1002 / ciuz.19780120305 .