Structure via PubChem · Public domain (PubChem)
o-phenylenediamine
Sign in to save'''o-Phenylenediamine (OPD') is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. OPD is a white compound although samples appear darker owing to oxidation by air. It is isomeric with m-phenylenediamine and p''-phenylenediamine.
Chemical data
- Formula
- C6H8N2
- Molecular weight
- 108.14 g/mol
- IUPAC name
- benzene-1,2-diamine
- SMILES
- C1=CC=C(C(=C1)N)N
- InChIKey
- GEYOCULIXLDCMW-UHFFFAOYSA-N
- XLogP
- 0.1
- Polar surface area
- 52 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Subclass of
- phenylenediamine
- Has part
- carbon
- Mass
- 108.06874825599999
Show 7 more facts
- canonical SMILES
- Nc1ccccc1N
- chemical formula
- C₆H₈N₂
- melting point
- 102.5
- Commons category
- 1,2-Diaminobenzene
- subject has role
- carcinogen
- boiling point
- 257
- ionization energy
- 7.20
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Preparation
- Reactions and uses
- Safety
- References
'''o-Phenylenediamine (OPD') is an organic compound with the formula C6H4(NH2)2. This aromatic diamine is an important precursor to many heterocyclic compounds. OPD is a white compound although samples appear darker owing to oxidation by air. It is isomeric with m-phenylenediamine and p-phenylenediamine.
==Preparation== Commonly, 2-nitrochlorobenzene is treated with ammonia to generate 2-nitroaniline, whose nitro group is then reduced: ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl H2NC6H4NO2 + 3 H2 → H2NC6H4NH2 + 2 H2O
Excerpted from Wikipedia’s “o-phenylenediamine” article, available under the CC BY-SA 4.0 licence.