m-Phenylenediamine

m-Phenylenediamine
Names
	Preferred IUPAC name Benzene-1,3-diamine
	Other names 1,3-Diaminobenzene; MPD
Identifiers
CAS Number	108-45-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	471357
ChEBI	CHEBI:8092 ;
ChEMBL	ChEMBL1595914;
ChemSpider	13836283 ;
ECHA InfoCard	100.003.259
EC Number	203-584-7;
KEGG	C02454;
PubChem CID	7935;
RTECS number	SS7700000;
UNII	OE624J2447 ;
UN number	1673
CompTox Dashboard (EPA)	DTXSID4021137 ;
	InChI InChI=1S/C6H8N2/c7-5-2-1-3-6(8)4-5/h1-4H,7-8H2 Key: WZCQRUWWHSTZEM-UHFFFAOYSA-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)
Acidity (pKa)	2.50 (doubly protonated form; 20 °C, H2O); 5.11 (conjugate acid; 20 °C, H2O);
Magnetic susceptibility (χ)	-70.53·10−6 cm3/mol
Hazards
GHS pictograms
GHS Signal word	Danger
GHS hazard statements	H301, H311, H317, H319, H331, H341, H400, H410
GHS precautionary statements	P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+310, P302+352, P304+340, P305+351+338, P308+313, P311, P312, P321, P322, P330, P333+313, P337+313, P361, P363, P391
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 [77 °F], 100 kPa).

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.^[2]

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.^[3]

References

^ Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89. ISBN 978-1498754286.
^ 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

[CRC97-1] Haynes, William M., ed. (2016). CRC Handbook of Chemistry and Physics (97th ed.). CRC Press. p. 5–89. ISBN 978-1498754286.

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

[3] 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

[1]

[2]

[3]