Chemistry:M-Phenylenediamine

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
EC Number	203-584-7
KEGG	C02454
PubChem CID	7935
RTECS number	SS7700000
UNII	OE624J2447 Y
UN number	1673
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)
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, 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
NFPA 704 (fire diamond)	1 3 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

Tracking categories (test):

• PairSizeSet

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.