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m-Phenylenediamine

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m-Phenylenediamine
Names
Preferred IUPAC name Benzene-1,3-diamine
Other names 1,3-Diaminobenzene
MPD
MPDA
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 471357
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.259 Edit this at Wikidata
EC Number
  • 203-584-7
KEGG
PubChem CID
RTECS number
  • SS7700000
UNII
UN number 1673
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2Key: WZCQRUWWHSTZEM-UHFFFAOYSA-N
  • InChI=1/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2Key: WZCQRUWWHSTZEM-UHFFFAOYAM
SMILES
  • c1cc(cc(c1)N)N
Properties
Chemical formula C6H8N2
Molar mass 108.1 g·mol
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)
Solubility in water 42.9 g/100 ml (20 °C)
Acidity (pKa)
  • 2.50 (doubly protonated form; 20 °C, H2O)
  • 5.11 (conjugate acid; 20 °C, H2O)
Magnetic susceptibility (χ) -70.53·10 cm/mol
Hazards
GHS labelling:
Pictograms GHS06: ToxicGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Signal word Danger
Hazard statements H301, H311, H317, H319, H331, H341, H410
Precautionary statements 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)
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 °C (369 °F; 460 K)
Autoignition
temperature 		560 °C (1,040 °F; 833 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. Samples often come as colourless flakes and may darken in storage.

Production

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

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.

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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