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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:
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)

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.

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

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
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)
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)
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)
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