m-Phenylenediamine, also called 1,3-diaminobenzene, is an organic compound with the formula C6H4(NH2)2. It is an isomer of o-phenylenediamine and p-phenylenediamine. This aromatic diamine is a colourless solid that appears as needles, but turns red or purple on exposure to air due to formation of oxidation products.[3] Samples often come as colourless flakes and may darken in storage.
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Names | |||
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Preferred IUPAC name
Benzene-1,3-diamine | |||
Other names
1,3-Diaminobenzene
MPD MPDA | |||
Identifiers | |||
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3D model (JSmol)
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471357 | |||
ChEBI |
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ChEMBL |
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ChemSpider |
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ECHA InfoCard | 100.003.259 | ||
EC Number |
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KEGG |
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PubChem CID
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RTECS number |
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UNII |
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UN number | 1673 | ||
CompTox Dashboard (EPA)
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Properties | |||
C6H8N2 | |||
Molar mass | 108.1 g·mol−1 | ||
Appearance | White solid | ||
Melting point | 64 to 66 °C (147 to 151 °F; 337 to 339 K) | ||
Boiling point | 282 to 284 °C (540 to 543 °F; 555 to 557 K) | ||
42.9 g/100 ml (20 °C) | |||
Acidity (pKa) |
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-70.53·10−6 cm3/mol | |||
Hazards | |||
GHS labelling: | |||
Danger | |||
H301, H311, H317, H319, H331, H341, H410 | |||
P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P302+P352, P304+P340, P305+P351+P338, P308+P313, P311, P312, P321, P322, P330, P333+P313, P337+P313, P361, P363, P391, P403+P233, P405, P501 | |||
NFPA 704 (fire diamond) | |||
Flash point | 187 °C (369 °F; 460 K) | ||
560 °C (1,040 °F; 833 K) | |||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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m-Phenylenediamine is produced by hydrogenation of 1,3-dinitrobenzene. The dinitrobenzene is prepared by dinitration of benzene.[4]
m-Phenylenediamine is used in the preparation of various polymers including aramid fibers, epoxy resins, wire enamel coatings and polyurea elastomers. Other uses for m-phenylenediamine include as an accelerator for adhesive resins, and as a component of dyes for leather and textiles. Basic Brown 1, Basic Orange 2, Direct Black 38, and Developed Black BH. In hair-dying, m-phenylenediamine is a "coupling agent", used to produce blue colors.[5]