m-Phenylenediamine

Names

IUPAC name

1,3-diaminobenzene

Other names

MPD

Identifiers

CAS Number

108-45-2^Y

ChEBI

CHEBI:8092^N

ChemSpider

13836283^N

Jmol interactive 3D

Image

UNII

OE624J2447^Y

InChI

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

SMILES

c1cc(cc(c1)N)N

Properties

Chemical formula

C₆H₈N₂

Molar mass

108.1

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)

Solubility in water

42.9 g/100 ml (20 °C)

Hazards

R-phrases

R23/24/25 R36/37/38 R40 R42/43

S-phrases

S22 S26 S36 S37 S39 S45

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 [77 °F], 100 kPa).

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Infobox references

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. It is a colourless solid.

Production

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

Applications

m-Phenylenediamine is used in the preparation 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 (Bismarck Brown), Basic Orange 2, Direct Black 38, and Developed Black BH In hair-dying, m-phenylenediamine is a "coupling agent", used to produce blue colors.^[2]

References

↑ Smiley, Robert A. (2000), "Phenylene- and Toluenediamines", Ullmann's Encyclopedia of Industrial Chemistry, doi:10.1002/14356007.a19_405, ISBN 3527306730
↑ 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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