o-Phenylenediamine

Chemical properties

White to off white solid

Chemical properties

o-Phenylenediamine is a white to brownish crystalline substance that turns red upon exposure to air.

The Uses of o-Phenylenediamine

o-Phenylenediamine is an amino substituted benzene used in the manufacture of dyes. Potential use in sensitive immunosensor for cancer biomarker.Environmental toxin on US EPA Toxic Release Inventory list (TRI) list.

The Uses of o-Phenylenediamine

It is actively involved in the preparation of pharmaceuticals by reacting substituted o-phenylenediamine with various diketones.

The Uses of o-Phenylenediamine

m-Phenylenediamine is used in the manu facture of a variety of dyes, in hair dyeformulations, as a rubber curing agent, inpetroleum additives, as a photographic developing agent, and as an analytical reagent.

The Uses of o-Phenylenediamine

o-Phenylenediamine is used as an intermediate in the manufacture of dyes, pigments, andfungicides. It is also used in hair dye formulation, as a photographic developing agent,and in organic synthesis.

What are the applications of Application

o-Phenylenediamine is used to detect horseradish peroxidase activity

Definition

ChEBI: A phenylenediamine in which the two amino groups are ortho to each other.

Synthesis Reference(s)

Organic Syntheses, Coll. Vol. 2, p. 501, 1943
Synthetic Communications, 25, p. 4025, 1995 DOI: 10.1080/00397919508011478

General Description

Colorless monoclinic crystals if pure; technical grade brownish-yellow crystals or a sandy brown solid. Used in manufacture of dyes, photography, organic synthesis.

Air & Water Reactions

Soluble in water [Hawley]. Melting point 219 F. Flash point 277 F. Toxic by skin absorption, inhalation or ingestion. Even as a solid will spot downwind area brown/purple (Roger Patrick, DuPont Engineer).

Reactivity Profile

o-Phenylenediamine a weak aromatic amine base neutralizes acids in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Darkens on exposure to air (Roger Patrick, DuPont Engineer).

Health Hazard

The toxic effects of m-phenylenediamineare similar to its ortho- and para-isomers.The toxic symptoms were tremor, excite ment, convulsions, and cyanosis, and col lapse at fatal dose. Other symptoms includeddecreased blood pressure and pulse rate.Chronic toxic effects resulting from the oralapplication of an aqueous solution of thiscompound were increase in liver and to alesser extent, kidney weights. No carcinogenicity was observed in test animals. Thecompound was excreted rapidly, unchanged.
LD50 value, oral (rats): 650 mg/kg.

Fire Hazard

Flash point data for o-Phenylenediamine are not available. o-Phenylenediamine is probably combustible.

Biochem/physiol Actions

o-Phenylenediamine (o-PD) is a potent substrate for spectrophotometric horseradish peroxidase (HRP)-mediated enzyme-linked immunosorbent assay (ELISA), which gives 2,3-diaminophenazine (DAP) as a product of o-PD oxidation.

Safety Profile

Confirmed carcinogen. Poison by ingestion and intraperitoneal routes. Moderately toxic by subcutaneous route. Mildly toxic by skin contact. Mutation data reported. A pesticide and pharmaceutical. When heated to decomposition it emits toxic fumes of NOx. See also other phenylenediamine entries and AMINES

Potential Exposure

Used as an intermediate in the making of dyes; pesticides, pharmaceuticals, and rubber chemicals; in making fungicides and other chemicals; in photographic and analytical procedures and processes

Carcinogenicity

o-PDA (dihydrochloride) induced hepatocellular carcinomas during an 18-month feeding study in male Charles River CD rats given diets containing 2000 or 4000 ppm of the chemical (female rats not used in this study). No significant carcinogenic effects were observed in male and female CD-1 mice given higher doses (6872 or 13,743 ppm) of the compound.

Shipping

UN1673 Phenylenediamines (o-, m-, p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.

Purification Methods

Crystallise the diamine from aqueous 1% sodium hydrosulfite (charcoal), wash it with ice-water and dry it in a vacuum desiccator, or sublime it in vacuo. It has been purified by recrystallisation from toluene and zone refined [Anson et al. J Am Chem Soc 108 6593 1986]. Purification by refluxing a CH2Cl2 solution containing charcoal is also carried out followed by evaporation and recrystallisation [Koola & Kochi J Org Chem 52 4545 1987], protect from light. The acetate has m 186o. [Beilstein 13 IV 38.]

Incompatibilities

Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, acid chlorides; acid anhydrides; chloroformates. Heat and light contribute to instability. Keep away from metals; 1,2-PHENYLENEDIAMINE a weak aromatic amine base neutralizes acids in exothermic reactions to form salts. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. Darkens on exposure to air (Roger Patrick, DuPont Engineer).

Waste Disposal

Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalytic or thermal device.