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3-Aminophenol Basic information
3-Aminophenol Chemical Properties
  • Melting point:121 °C
  • Boiling point:164 °C11 mm Hg(lit.)
  • Density 0.99
  • refractive index 1.5444 (estimate)
  • Flash point:155 °C
  • storage temp. 2-8°C
  • solubility 26g/l
  • form Crystalline Powder
  • Colour Index 76545
  • pka4.37, 9.82(at 20℃)
  • color White to pinkish or light gray
  • Odorodorless
  • PH6.8 (10g/l, H2O, 20℃)
  • Water Solubility 35 g/L (20 ºC)
  • Merck 14,460
  • BRN 636059
  • Stability:Stable. Combustible. Incompatible with strong oxidizing agents, bases, mineral acids. May be light or air-sensitive.
  • CAS DataBase Reference591-27-5(CAS DataBase Reference)
  • NIST Chemistry ReferencePhenol, 3-amino-(591-27-5)
  • EPA Substance Registry System3-Aminophenol (591-27-5)
Safety Information
  • Hazard Codes Xn,N
  • Risk Statements 20/22-51/53
  • Safety Statements 28-61-28A
  • RIDADR UN 2512 6.1/PG 3
  • WGK Germany 2
  • RTECS SJ4900000
  • TSCA Yes
  • HazardClass 6.1
  • PackingGroup III
  • HS Code 29222900
  • Hazardous Substances Data591-27-5(Hazardous Substances Data)
  • ToxicityLD50 i.p. in mice: 4.5 mg/20g (Koelzer, Giesen)
3-Aminophenol Usage And Synthesis
  • Chemical PropertiesLight grey crystal powder
  • Chemical Propertieso-Aminophenol appears as colorless needles or as white crystalline substance turning tan to brown on exposure to air.
  • Usesm-Aminophenol (MAP) is an important starting material for dyes, including a variety of leuco (or latent) dyes used in imaging technology, optical bleaches and fluorescent agents, drugs, agricultural chemicals; and high-performance polymers. Although the synthesis of m-aminophenol(s) by the reaction of resorcinol with ammonia or (di)alkylarnines has been known for about 100 years,the preferred manufacturing process had been for many years a route involving the sulfonation of nitrobenzene to m-nitrobenzenesulfonic acid, the reduction of the nitro group to give m-aminobenzenesulfonic acid, followed by the caustic fusion of sodium m-aminobenzenesulfonate to yield sodium m-aminophenolate. The m-aminophenol was isolated/purified by neutralization, filtration, and recrystallization; the overall yield of m-aminophenol from nitrobenzene was estimated by SRI International to be 58%. (Doubtless, process improvements were made by the producers using this process.) The nitrobenzene/sulfonationlreductionlcaustic fusion route is still being used commercially, notably by ACNA in Italy, the largest producer of MAP, as well as a few smaller manufacturers. Sumitomo Chemical Co. used this process as well into the early 1980s and had licensed their knowhow to Hindustani Organic Chemicals, Ltd. of India which started up a plant on this basis with a capacity for MAP of 1.5 mill. lb /yr in 1970.The output of the Indian plant was said to be devoted to making sodium p-aminosalycilate (PAS), a tuberculostatic agent.
  • Usescoupler for hair dyes; dye intermediate; in the manufacturing of 4-aminosalicylic acid
  • UsesDye intermediate, manufacture of p-aminosalicylic acid.
  • DefinitionChEBI: An aminophenol that is one of three amino derivatives of phenol which has the single amino substituent located meta to the phenolic -OH group.
  • Synthesis Reference(s)Tetrahedron Letters, 25, p. 1479, 1984 DOI: 10.1016/S0040-4039(01)80191-X
  • General DescriptionWhite crystals or off-white flakes.
  • Air & Water Reactions3-Aminophenol may be sensitive to prolonged exposure to air and light. Slightly soluble in water.
  • Reactivity Profile3-Aminophenol may react with strong oxidizers and mineral acids or bases.
  • HazardToxic by ingestion.
  • Fire HazardFlash point data for 3-Aminophenol are not available. 3-Aminophenol is probably combustible.
  • Safety ProfilePoison by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. A skin and eye irritant. When heated to decomposition it emits toxic fumes of NOx,.
  • Potential ExposureWorkers may be exposed to oAminophenol during its use as a chemical intermediate; in the manufacture of azo and sulfur dyes; and in the photographic industry. There is potential for consumer exposure to o-Aminophenol because of its use in dyeing hair, fur, and leather. The compound is a constituent of 75 registered cosmetic products suggesting the potential for widespread consumer exposure. p-Aminophenol is used mainly as a dye, dye intermediate and as a photographic developer; and in small quantities in analgesic drug preparation. Consumer exposure to p-aminophenol may occur from use as a hairdye or as a component in cosmetic preparations. mAminophenol is used mainly as a dye intermediate
  • ShippingUN2512 Aminophenols (o-; m-; p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials
  • Purification MethodsCrystallise it from hot water or toluene. [Beilstein 13 IV 952.]
  • IncompatibilitiesThese phenol/cresol materials can react with oxidizers; reaction may be violent. Incompatible with strong reducing substances such as alkali metals, hydrides, nitrides, and sulfides. Flammable gas (H2) may be generated, and the heat of the reaction may cause the gas to ignite and explode. Heat may be generated by the acidbase reaction with bases; such heating may initiate polymerization of the organic compound. Reacts with boranes, alkalies, aliphatic amines, amides, nitric acid, sulfuric acid. Phenols are sulfonated very readily (e.g., by concentrated sulfuric acid at room temperature). These reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid and can explode when heated. Many phenols form metal salts that may be detonated by mild shock.
  • Waste DisposalDissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed.
3-Aminophenol Preparation Products And Raw materials
3-Aminophenol(591-27-5)Related Product Information
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