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P23938

Sigma-Aldrich

o-Phenylenediamine

flaked, 99.5%

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:
24898319
NACRES:
NA.22

vapor density

3.7 (vs air)

Quality Level

200

vapor pressure

0.01 mmHg ( 25 °C)

Assay

99.5%

form

powder

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:
  • To prepare quinoxalines, benzimidazoles, and 1H-1,5-benzodiazepines by condensing with aryl aldehydes or ketones.
  • In the H2O mediated one-pot preparation of 1,2-disubstituted benzimidazoles by reacting with aldehydes in the presence of trimethylsilyl chloride.
  • In the copper-catalyzed synthesis of alkyne substituted quinoxalines by reacting with terminal alkynes.
  • In the preparation of 1,5-benzodiazepine derivatives by reacting with different ketones under neat reaction conditions via ytterbium trichloride catalyzed condensation reaction.

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

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Syntheses of Benzimidazoles, Quinoxalines and 3, 3-Dihydro-1H-1, 5-benzodiazepines Starting from o-Phenylenediamine
Yong Cui, et al.
Chin. J. Chem., 23(5), 589-595 (2005)
Efficient Synthesis of 1, 5-Benzodiazepine Derivatives by Ytterbium Trichloride-Catalyzed Condensation of o-Phenylenediamine and Ketones
Wu J, et al.
Synthetic Communications, 36(4), 457-464 (2006)
Water mediated chemoselective synthesis of 1, 2-disubstituted benzimidazoles using o-phenylenediamine and the extended synthesis of quinoxalines
Wan J, et al.
Green Chemistry, 11(10), 1633-1637 (2009)
Galber Rodrigues Araujo et al.
Arthritis research & therapy, 17, 168-168 (2015-06-24)
Rheumatoid arthritis (RA) is a chronic inflammatory autoimmune disease that affects around 1% of the human population worldwide. RA diagnosis can be difficult as there is no definitive test for its detection. Therefore, the aim of this study was to
Hai-Long Wang et al.
Acta tropica, 137, 58-66 (2014-05-13)
Nasal vaccination is an effective therapeutic regimen for preventing certain infectious diseases. The mucosal immune response is important for resistance to Toxoplasma gondii infection. In this study, we evaluated the immune responses elicited in BALB/c mice by nasal immunisation with
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