| Identification | More | [Name]
3-Aminophenol | [CAS]
591-27-5 | [Synonyms]
3-AMINO-1-HYDROXYBENZENE
3-AMINOPHENOL
3-HYDROXYANILINE
5-AMINO-PHENOL
AMINOPHENOL-3
LABOTEST-BB LTBB000485
M-AMINOPHENOL
META AMINO PHENOL
M-HYDROXYANILINE
1-Amino-3-hydroxybenzene
1-amino-3-hydroxybenzene[qr]
3-amino-1-hydroxybenzene[qr]
3-amino-pheno
3-hydroxyaniline[qr]
3-Hydroxyanilinel AC
3-hydroxybenzenamine
Basf ursol eg
basfursoleg
C.I. 76545
C.I. Oxidation Base 7 | [EINECS(EC#)]
209-711-2 | [Molecular Formula]
C6H7NO | [MDL Number]
MFCD00007786 | [Molecular Weight]
109.13 | [MOL File]
591-27-5.mol |
| Chemical Properties | Back Directory | [Appearance]
o-Aminophenol appears as colorless needles or as white crystalline substance turning tan to brown on exposure to air. | [Melting point ]
120-124 °C (lit.) | [Boiling point ]
164 °C/11 mmHg (lit.) | [density ]
0.99 | [vapor pressure ]
0.019Pa at 20℃ | [refractive index ]
1.5444 (estimate) | [Fp ]
155 °C
| [storage temp. ]
2-8°C | [solubility ]
26g/l | [Colour Index ]
76545 | [form ]
Crystalline Powder | [pka]
4.37, 9.82(at 20℃) | [color ]
White to pinkish or light gray | [Odor]
odorless | [PH]
6.8 (10g/l, H2O, 20℃) | [Stability:]
Stable. Combustible. Incompatible with strong oxidizing agents, bases, mineral acids. May be light or air-sensitive. | [Water Solubility ]
35 g/L (20 ºC) | [Merck ]
14,460 | [BRN ]
636059 | [LogP]
0.183 at 20℃ | [Uses]
m-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. | [CAS DataBase Reference]
591-27-5(CAS DataBase Reference) | [NIST Chemistry Reference]
Phenol, 3-amino-(591-27-5) | [EPA Substance Registry System]
3-Aminophenol (591-27-5) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,N | [Risk Statements ]
R20/22:Harmful by inhalation and if swallowed .
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment . | [Safety Statements ]
S28:After contact with skin, wash immediately with plenty of ... (to be specified by the manufacturer) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet . | [RIDADR ]
UN 2512 6.1/PG 3
| [WGK Germany ]
2
| [RTECS ]
SJ4900000
| [TSCA ]
Yes | [HazardClass ]
6.1 | [PackingGroup ]
III | [HS Code ]
29222900 | [Safety Profile]
Poison 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,. | [Hazardous Substances Data]
591-27-5(Hazardous Substances Data) | [Toxicity]
LD50 i.p. in mice: 4.5 mg/20g (Koelzer, Giesen) |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
Sodium hydroxide-->Hydrochloric acid-->Sulfuric acid-->Potassium hydroxide-->FUMING SULFURIC ACID-->Sodium sulfite-->Water-->Nitrobenzene-->Metanilic acid-->Benzenesulfonic acid sodium salt-->METANILIC ACID SODIUM SALT | [Preparation Products]
Resorcinol-->10-(2-Benzothiazolyl)-2,3,6,7-tetrahydro-1,1,7,7-tetramethyl-1H,5H,11H-(1)benzopyropyrano(6,7-8-I,j)quinolizin-11-one-->4-Aminosalicylic acid-->GLY-7-AMINO-4-METHYLCOUMARIN-->ERYTHROSIN B-->Rhodamine 123-->7-Hydroxyquinoline-->3-Bromophenol-->Coumarin 314T-->Coumarin 120-->Nedocromil-->3-Ethoxyaniline-->Phenmedipham-->9-Formyl-8-hydroxy-1,1,7,7-tetramethyljulolidine-->RHODAMINE 110-->Mepronil-->Direct Black 168-->ETHYL (3-HYDROXYPHENYL)CARBAMATE-->Coumarin 151-->3-ISOPROPOXYANILINE-->fluorescent whitening agent SWN-->3-dimethylaminophenyl dimethylcarbamate-->3-Dimethylaminophenol-->Sodium 4-aminosalicylate |
| Hazard Information | Back Directory | [General Description]
White crystals or off-white flakes. | [Reactivity Profile]
M-AMINOPHENOL(591-27-5) may react with strong oxidizers and mineral acids or bases. | [Air & Water Reactions]
This compound may be sensitive to prolonged exposure to air and light. Slightly soluble in water. | [Hazard]
Toxic by ingestion.
| [Potential Exposure]
Workers 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 | [Fire Hazard]
Flash point data for this chemical are not available. M-AMINOPHENOL is probably combustible. | [First aid]
If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit. | [Shipping]
UN2512 Aminophenols (o-; m-; p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials | [Incompatibilities]
These 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. | [Chemical Properties]
Light grey crystal powder | [Chemical Properties]
o-Aminophenol appears as colorless needles or as white crystalline substance turning tan to brown on exposure to air. | [Waste Disposal]
Dissolve 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. | [Application]
3-Aminophenol has been used in the synthesis of disulfonated bis[4-(3-aminophenoxy)phenyl]sulfone (S-BAPS).
It can be used to synthesize:
Methyl 2-oxo-7-[(triphenylphosphoranylidene)amino]-2H-chromene-4-carboxylate by reacting with dimethyl acetylenedicarboxylate (DMAD) in the presence of triphenylphosphine.
3-Amino-2-cyclohexen-1-one via palladium-catalyzed hydrogenation. | [Definition]
ChEBI: 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 | [Flammability and Explosibility]
Nonflammable | [Synthesis]
3-Amino-2-cyclohexene-1-one (1.5 mol, 166.7 g), potassium acetate (6 mmol, 0.6 g), and 5% palladium on carbon (4.7 g, 65.5% water) were added to N, N-dimethylacetamide (475 g) solvent in one liter creased round bottom flask equipped with a nitrogen purge, thermometer, condenser, distillation head, overhead stirrer, and heating mantle. The solution was then heated to reflux for two hours at 173° C. with a continuous nitrogen purge. The palladium catalyst was filtered from the solution. Gas chromatography analysis indicated 130.9 g 3-aminophenol (1.2 mole, 80% yield based on 3-amino-2-cyclohexene-1-one).
| [Purification Methods]
Crystallise it from hot water or toluene. [Beilstein 13 IV 952.] |
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