''m''-Phenylenediamine, also called 1,3-diaminobenzene, is an

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon-hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. The ...

with the

formula In science, a formula is a concise way of expressing information symbolically, as in a mathematical formula or a ''chemical formula''. The informal use of the term ''formula'' in science refers to the general construct of a relationship betwee ...

C₆H₄(NH₂)₂. It is an isomer of ''o''-phenylenediamine and ''p''-phenylenediamine. This

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

diamine A diamine is an amine with exactly two amino groups. Diamines are used as monomers to prepare polyamides, polyimides, and polyureas. The term ''diamine'' refers mostly to primary diamines, as those are the most reactive. In terms of quantities p ...

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 di

nitration In organic chemistry, nitration is a general class of chemical processes for the introduction of a nitro group into an organic compound. The term also is applied incorrectly to the different process of forming nitrate esters between alcohols and ...

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

Applications

''m''-Phenylenediamine is used in the preparation of various

polymer A polymer (; Greek '' poly-'', "many" + ''-mer'', "part") is a substance or material consisting of very large molecules called macromolecules, composed of many repeating subunits. Due to their broad spectrum of properties, both synthetic a ...

s including

aramid Aramid fibers, short for aromatic polyamide, are a class of heat-resistant and strong synthetic fibers. They are used in aerospace and military applications, for ballistic-rated body armor fabric and ballistic composites, in marine cordage, ma ...

fibers,

epoxy resin Epoxy is the family of basic components or cured end products of epoxy resins. Epoxy resins, also known as polyepoxides, are a class of reactive prepolymers and polymers which contain epoxide groups. The epoxide functional group is also coll ...

s, wire enamel coatings and polyurea

elastomer An elastomer is a polymer with viscoelasticity (i.e. both viscosity and elasticity) and with weak intermolecular forces, generally low Young's modulus and high failure strain compared with other materials. The term, a portmanteau of ''elastic p ...

s. 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.

References

{{DEFAULTSORT:Phenylenediamine, m- Diamines Anilines