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T7394

Sigma-Aldrich

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

99%, powder

Synonym(s):

TMPD, TMPDA, TMPPD, Wurster’s reagent

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About This Item

Linear Formula:
C6H4[N(CH3)2]2
Molecular Weight:
164.25
Beilstein/REAXYS Number:
1564025
EC Number:
202-831-6
MDL number:
MFCD00008309
UNSPSC Code:
12352100
PubChem Substance ID:
57654696
NACRES:
NA.22

Quality Level

200

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.

Caution

May darken in storage.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 1

flash_point_f

230.0 °F - closed cup

flash_point_c

110 °C - closed cup

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF4377V
WXBF2758V
WXBD9800V
WXBD6696V
WXBD4862V

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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)
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)
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
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
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