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694975

Sigma-Aldrich

o-Phenylenediamine

sublimed, ≥99%

Synonym(s):
1,2-Diaminobenzene, OPD, 1,2-Phenylenediamine
Empirical Formula (Hill Notation):
C6H8N2
CAS Number:
Molecular Weight:
108.14
Beilstein:
606074
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

vapor density

3.7 (vs air)

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.

Packaging

1 g in glass bottle

Signal Word

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 Code

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

WGK

WGK 3

Flash Point(F)

276.8 °F - closed cup

Flash Point(C)

136 °C - closed cup

Certificate of Analysis

Enter Lot Number to search for Certificate of Analysis (COA).

Certificate of Origin

Enter Lot Number to search for Certificate of Origin (COO).

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)
Nitrogen-doped graphene nanoplatelets from simple solution edge-functionalization for n-type field-effect transistors.
Chang DW, et al.
Journal of the American Chemical Society, 135(24), 8981-8988 (2013)
Nitrogen-doped colloidal graphene quantum dots and their size-dependent electrocatalytic activity for the oxygen reduction reaction.
Li Q, et al.
Journal of the American Chemical Society, 134(46), 18932-18935 (2012)
Pyrazinacenes: Aza Analogues of Acenes.
Richards GJ, et al.
The Journal of Organic Chemistry, 74(23), 8914-8923 (2009)

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