O-Phenylenediamine

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IUPACName = Benzene-1,2-diamine
OtherNames = "o"-Phenylenediamine
1,2-Diaminobenzene
Reference = [http://www.dupont.com/specintermediates/opd.html DuPont Specialty Intermediates: o-Phenylenediamine (OPD) ] ]
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CASNo = 95-54-5
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SMILES = Nc1ccccc1N
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Formula = C₆H₈N₂
MolarMass = 108.1 g/mol
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Density = 1.031 g/cm³
MeltingPtCL = 102
MeltingPtCH = 104
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ExternalMSDS = [http://msds.chem.ox.ac.uk/PH/o-phenylenediamine.html Oxford MSDS]
EUClass = Toxic (T); Dangerous for the environment (N)
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"o"-Phenylenediamine is a chemical compound with the formula C₆H₄(NH₂)₂. This aromatic diamine is an important precursor to many heterocycles. It is isomeric with "m"-phenylenediamine and "p"-phenylenediamine.

"o"-Phenylenediamine condenses with ketones and aldehydes to give rise to Schiff bases. This reaction allows the synthesis of substituted benzimidazoles. Also, quinoxaline dione may be prepared by condensation of "o"-phenylenediamine with dimethyl oxalate.

In coordination chemistry, phenylenediamine is an important ligand precursor. Schiff base derivatives, such as those derived from salicylaldehyde, are excellent chelating ligands. Oxidation of its metal-phenylenediamine complexes affords the diimine derivatives, which are intensely coloured and often exist in multiple stable oxidation states. [Warren, L. F. "Synthesis of [M'-N₄] and [M'-N₆] Complexes Based on "o"-Benzoquinone Diimine with Cobalt, Iron, and Ruthenium" Inorganic Chemistry 1977, volume 16, pages 2814-2819.]

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