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 labelling:
Pictograms
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
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). verify (what is ?) 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.^[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

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

[Ullmann-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

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