o-Phenylenediamine
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| O-Phenylenediamine[1] | |
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| IUPAC name | Benzene-1,2-diamine |
| Other names | o-Phenylenediamine 1,2-Diaminobenzene |
| Identifiers | |
| CAS number | [95-54-5] |
| SMILES | Nc1ccccc1N |
| Properties | |
| Molecular formula | C6H8N2 |
| Molar mass | 108.1 g/mol |
| Density | 1.031 g/cm3 |
| Melting point |
102-104 °C, 375-377 K, 216-219 °F |
| Boiling point |
252 °C, 525 K, 486 °F |
| Hazards | |
| NFPA 704 |
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| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references |
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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.[2]
[edit] References
- ^ DuPont Specialty Intermediates: o-Phenylenediamine (OPD)
- ^ 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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