m-Phenylenediamine

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.

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
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 ☒N
    Key: WZCQRUWWHSTZEM-UHFFFAOYSA-N ☒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 °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)
  • 2.50 (doubly protonated form; 20 °C, H2O)
  • 5.11 (conjugate acid; 20 °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 diamond
3
1
0
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).
☒N verify (what is checkY☒N ?)
Infobox references

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]

References
  1. Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89. ISBN 978-1498754286.
  2. "m-Phenylenediamine MSDS". Thermo Fisher Scientific.
  3. "1,3-PHENYLENEDIAMINE | CAMEO Chemicals | NOAA". CAMEO Chemicals. Retrieved 27 November 2021.
  4. Smiley, Robert A. (2000), "Phenylene- and Toluenediamines", Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a19_405, ISBN 3527306730
  5. Clausen, Thomas; Schwan-Jonczyk, Annette; Lang, Günther; Schuh, Werner; Liebscher, Klaus Dieter; Springob, Christian; Franzke, Michael; Balzer, Wolfgang; Imhoff, Sonja; Maresch, Gerhard; Bimczok, Rudolf (2006), "Hair Preparations", Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a12_571.pub2, ISBN 3527306730
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