Tetramethylphenylenediamine

Structural formula
General
Surname	Tetramethylphenylenediamine (TMPD)
other names	Tetramethyl- p- phenylenediamine; N , N , N ', N ' -tetramethyl-1,4-phenylenediamine; Wurster reagent;
Molecular formula	C 10 H 16 N 2
Brief description	light pink solid
External identifiers / databases
EC number	202-831-6
ECHA InfoCard	100.002.574
PubChem	7490
ChemSpider	21106585
Wikidata	Q408762
properties
Molar mass	164.25 g mol −1
Physical state	firmly
Melting point	48-50 ° C
boiling point	260 ° C
pK s value	6.35
solubility	heavy in water (646 mg l −1 at 25 ° C)
safety instructions
GHS hazard labeling from Regulation (EC) No. 1272/2008 (CLP) , expanded if necessary Caution
H and P phrases	H: 332-312-302
	P: 280
Toxicological data	500 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 .

Tetramethylphenylenediamine ( TMPD ), more precisely N , N , N ', N ' -tetramethyl-1,4-phenylenediamine, is a derivative of p -phenylenediamine . It is an aromatic organic compound and forms colorless, light-sensitive, leafy crystals with a characteristic odor.

properties

Tetramethyl- p -phenylenediamine, like all derivatives of p -phenylenediamine, forms stable, colored semiquinonediimine radical cations (Wurster blue) when an electron is released . Colorless quinonediimine dications result from the further release of an electron .

use

TMPD is used as a redox indicator . In microbiology, TMPD (Kovacs reagent) is used to detect the enzyme cytochrome c oxidase in cells ( oxidase test ).

Other names

Wurster blue reagent, after Casimir Wurster (1854–1913). Wurster used it to detect wood pulp in paper analysis, as did dimethylphenylenediamine (Wurster's red).

Web links

Wursters Blau - Oxidation of tetramethyl-p-phenylenediamine ( Memento from June 19, 2012 in the Internet Archive )

Individual evidence

↑ ^a ^b ^c ^d ^e Entry on N, N, N ′, N′-tetramethyl-p-phenylenediamine in the GESTIS substance database of the IFA , accessed on February 18, 2017(JavaScript required) .
↑ ^a ^b ^c Entry on tetramethylphenylenediamine in the ChemIDplus database of the United States National Library of Medicine (NLM)
↑ Entry on N, N, N ′, N′-tetramethyl-p-phenylenediamine 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 .
^ U. Nickel: Reactions with Wurster's cations. In: Chemistry in Our Time . Volume 12, 1978, pp. 89-98, doi: 10.1002 / ciuz.19780120305 .

[GESTIS-1] Entry on N, N, N ′, N′-tetramethyl-p-phenylenediamine in the GESTIS substance database of the IFA , accessed on February 18, 2017(JavaScript required) .

[ChemIDplus-2] Entry on tetramethylphenylenediamine in the ChemIDplus database of the United States National Library of Medicine (NLM)

[CLP_100.002.574-3] Entry on N, N, N ′, N′-tetramethyl-p-phenylenediamine 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 .

[4] U. Nickel: Reactions with Wurster's cations. In: Chemistry in Our Time . Volume 12, 1978, pp. 89-98, doi: 10.1002 / ciuz.19780120305 .