T7394

Sigma-Aldrich

N,N,N′,N′-Tetramethyl-p-phenylenediamine

99%, powder

Synonym(s):
TMPD, Wurster’s reagent, TMPDA, TMPPD
Linear Formula:
C6H4[N(CH3)2]2
Molecular Weight:
164.25
Beilstein/REAXYS Number:
1564025
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

assay

99%

form

flakes
powder

color

off-white to brown

bp

260 °C (lit.)

mp

49-51 °C (lit.)

SMILES string

CN(C)c1ccc(cc1)N(C)C

InChI

1S/C10H16N2/c1-11(2)9-5-7-10(8-6-9)12(3)4/h5-8H,1-4H3

InChI key

CJAOGUFAAWZWNI-UHFFFAOYSA-N

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General description

N,N,N′,N′-Tetramethyl-p-phenylenediamine (TMPDA) is a redox reagent with low ionization potential widely used as an electron donor for photosystem I. It also acts as an electron acceptor in photosystem II.

Application

N,N,N′,N′-Tetramethyl-p-phenylenediamine (TMPDA) can be used:
  • In the flow injection analysis of benzoyl peroxide.
  • To study photoinduced electron transfer to halogenated solvents.

Packaging

5, 25 g in glass bottle

Caution

May darken in storage.

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

hazcat

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral

storage_class_code

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK Germany

WGK 1

Flash Point(F)

230.0 °F - closed cup

Flash Point(C)

110 °C - closed cup

Certificate of Analysis

Certificate of Origin

Ultrafast photoinduced electron transfer from N, N, N′ , N′ -tetramethyl-p-phenylenediamine and N, N, N′ , N′ -tetramethylbenzidine to dichloromethane
Boilet L, et al.
Journal of Photochemistry and Photobiology A: Chemistry, 163(3), 529-536 (2004)
Interaction of N, N, N′ ,N′ -tetramethyl-p-phenylenediamine with photosystem II as revealed by thermoluminescence: reduction of the higher oxidation states of the Mn cluster and displacement of plastoquinone from the QB niche
Gauthier A, et al.
Biochimica et Biophysica Acta, 1757(11), 1547-1556 (2006)
Flow injection analysis of benzoyl peroxide using N, N, N, N-tetramethyl-p-phenylenediamine (TMPDA) and surfactants
Pharr DY & Tomsyck JA
Analytical Letters, 42(5), 821-832 (2009)
Youngno Kim et al.
Scientific reports, 10(1), 16488-16488 (2020-10-07)
Stretchable materials are essential for next generation wearable and stretchable electronic devices. Intrinsically stretchable and highly conductive polymers (termed ISHCP) are designed with semi interpenetrating polymer networks (semi-IPN) that enable polymers to be simultaneously applied to transparent electrodes and electrochromic...
P P Bawol et al.
Physical chemistry chemical physics : PCCP, 20(33), 21447-21456 (2018-08-09)
The reversibility of current Li-O2 batteries suffers from high charging overpotentials. To address this problem, the use of redox mediators has been proposed, which are supposed to improve the sluggish reaction kinetics of the oxygen evolution reaction via a solution...

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