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
CAS Number	108-45-2 Y
3D model (JSmol)	Interactive image
Beilstein Reference	471357
ChEBI	CHEBI:8092 N
ChEMBL	ChEMBL1595914
ChemSpider	13836283 N
ECHA InfoCard	100.003.259
EC Number	203-584-7
KEGG	C02454
PubChem CID	7935
RTECS number	SS7700000
UNII	OE624J2447 Y
UN number	1673
CompTox Dashboard (EPA)	DTXSID4021137
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 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)
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)[1]
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
NFPA 704 (fire diamond)	[2] 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 [77 °F], 100 kPa). N verify (what is YN ?) 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]