M-Phenylenediamine

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick facts Names, Identifiers ...
m-Phenylenediamine
Names
Preferred IUPAC name
Benzene-1,3-diamine
Other names
1,3-Diaminobenzene
MPD
MPDA
Identifiers
3D model (JSmol)
471357
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.259 Edit this at Wikidata
EC Number
  • 203-584-7
KEGG
RTECS number
  • SS7700000
UNII
UN number 1673
  • InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2 â˜’N
    Key: WZCQRUWWHSTZEM-UHFFFAOYSA-N â˜’N
  • InChI=1/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2
    Key: WZCQRUWWHSTZEM-UHFFFAOYAM
  • c1cc(cc(c1)N)N
Properties
C6H8N2
Molar mass 108.1 g·mol−1
Appearance White solid
Melting point 64 to 66 Â°C (147 to 151 Â°F; 337 to 339 K)
Boiling point 282 to 284 Â°C (540 to 543 Â°F; 555 to 557 K)
42.9 g/100 ml (20 °C)
Acidity (pKa)
  • 2.50 (doubly protonated form; 20 Â°C, H2O)
  • 5.11 (conjugate acid; 20 Â°C, H2O)[1]
−70.53·10−6 cm3/mol
Hazards
GHS labelling:
GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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)
[2]
NFPA 704 four-colored diamondHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
3
1
0
Flash point 187 Â°C (369 Â°F; 460 K)
560 Â°C (1,040 Â°F; 833 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
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Production

m-Phenylenediamine is produced by hydrogenation of 1,3-dinitrobenzene. The dinitrobenzene is prepared by dinitration of benzene.[4]

Applications

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] It has a role to play in the synthesis of a compound that is called Salermide.

References

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