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694975

Sigma-Aldrich

o-Phenylenediamine

sublimed, ≥99%

Synonym(s):

1,2-Diaminobenzene, 1,2-Phenylenediamine, OPD

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About This Item

Empirical Formula (Hill Notation):
C6H8N2
CAS Number:
95-54-5
Molecular Weight:
108.14
Beilstein/REAXYS Number:
606074
EC Number:
202-430-6
MDL number:
MFCD00007721
UNSPSC Code:
12352100
PubChem Substance ID:
329761704
NACRES:
NA.22

vapor density

3.7 (vs air)

Quality Level

100

vapor pressure

0.01 mmHg ( 25 °C)

assay

≥99%

form

sublimed

bp

256-258 °C

mp

100-102 °C

SMILES string

Nc1ccccc1N

InChI

1S/C6H8N2/c7-5-3-1-2-4-6(5)8/h1-4H,7-8H2

InChI key

GEYOCULIXLDCMW-UHFFFAOYSA-N

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Application

o-Phenylenediamine can be used in the synthesis of:
  • Various benzimidazole derivatives that are structural units of several bioactive drug substances and pigments.
  • N-doped colloidal graphene quantum dots (QDs), which can electrochemically catalyze the oxygen reduction reactions.
  • N-doped graphene nanoplatelets from simple solution edge-functionalization for n-type field-effect transistors.
  • N-heteroacenes (azaacenes) that are good candidates as active materials for organic thin film transistors.

signalword

Danger

Hazard Classifications

Acute Tox. 3 Oral - Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Aquatic Acute 1 - Aquatic Chronic 1 - Carc. 2 - Eye Irrit. 2 - Muta. 2 - Skin Sens. 1

Storage Class

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

wgk_germany

WGK 3

flash_point_f

276.8 °F - closed cup

flash_point_c

136 °C - closed cup

Certificates of Analysis (COA)

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Mild and highly efficient method for the synthesis of 2-arylbenzimidazoles and 2-arylbenzothiazoles.
Bahrami K, et al.
The Journal of Organic Chemistry, 73(17), 6835-6837 (2008)
Extension of N?Heteroacenes through a Four?Membered Ring.
Yang S, et al.
Chemistry?A European Journal , 22(19), 6637-6642 (2016)
Versatile 2, 7-substituted pyrene synthons for the synthesis of pyrene-fused azaacenes.
More S, et al.
Organic Letters, 14(16), 4170-4173 (2012)
Pyrazinacenes: Aza Analogues of Acenes.
Richards GJ, et al.
The Journal of Organic Chemistry, 74(23), 8914-8923 (2009)
Omar Dagdag et al.
Scientific reports, 9(1), 11715-11715 (2019-08-14)
Present study is designed for the synthesis, characterization and corrosion inhibition behavior of two diamine aromatic epoxy pre-polymers (DAEPs) namely, N1,N1,N2,N2-tetrakis (oxiran-2-ylmethyl) benzene-1,2-diamine (DAEP1) and 4-methyl-N1,N1,N2,N2-tetrakis (oxiran-2-ylmethyl) benzene-1,2-diamine (DAEP2) for carbon steel corrosion in acidic medium. Synthesized DAEPs were characterized
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