3-Aminophenol Property

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)

Flash point:

155 °C

storage temp. 

2-8°C

solubility 

26g/l

form 

Crystalline Powder

pka

4.37, 9.82(at 20℃)

Colour Index 

76545

color 

White to pinkish or light gray

PH

6.8 (10g/l, H2O, 20℃)

Odor

odorless

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.

LogP

0.183 at 20℃

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

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 Data

591-27-5(Hazardous Substances Data)

Toxicity

LD50 i.p. in mice: 4.5 mg/20g (Koelzer, Giesen)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H319Causes serious eye irritation

H411Toxic to aquatic life with long lasting effects

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P273Avoid release to the environment.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

3-Aminophenol Chemical Properties,Usage,Production

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.

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.

Uses

3-Aminophenol is an aromatic compound used in the preparation of inhibitors of mammalian carbonic anhydrase isoforms. Also used in the preparation of quinoline tethered fluorescent carbon dots for regulated anticancer discovery.

Uses

Dye intermediate, manufacture of p-aminosalicylic acid.

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

General Description

White crystals or off-white flakes.

Air & Water Reactions

3-Aminophenol may be sensitive to prolonged exposure to air and light. Slightly soluble in water.

Reactivity Profile

3-Aminophenol may react with strong oxidizers and mineral acids or bases.

Hazard

Toxic by ingestion.

Fire Hazard

Flash point data for 3-Aminophenol are not available. 3-Aminophenol is probably combustible.

Flammability and Explosibility

Non flammable

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,.

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).

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

Shipping

UN2512 Aminophenols (o-; m-; p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials

Purification Methods

Crystallise it from hot water or toluene. [Beilstein 13 IV 952.]

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.

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.