3D Mol Similar

3-Aminophenol

: Iupac Name：3-aminophenol; CAS No.: 591-27-5; Molecular Weight：109.128; Modify Date.: 2022-11-05 05:09; Introduction: 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. View more+

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1. Names and Identifiers

: 1.1 Name; 3-Aminophenol; 1.2 Synonyms; (3-Hydroxyphenyl)amine 1-Amino-3-hydroxybenzene 1-amino-3-hydroxybenzene[qr] 3-AMINO-1-HYDROXYBENZENE 3-Hydroxyaniline 3-Hydroxybenzenamine C.I. 76545 C.I. Oxidation Base 7 Fouramine EG Fourrine 65 Fourrine EG Furro EG Futramine EG LABOTEST-BB LTBB000485 M-AMINOPHENOL META AMINO PHENOL m-Hydroxyaminobenzene M-HYDROXYANILINE m-Hydroxyphenylamine Nako TEG NSC 1546 Pelagol EG Phenol, 3-amino- Phenol, m-amino- Renal EG Rodol EG Tertral EG Ursol EG Zoba EG; View all

1.3 CAS No.: 591-27-5

1.4 CID: 11568

1.5 EINECS(EC#): 209-711-2

1.6 Molecular Formula: C6H7NO (isomer)

1.7 Inchi: InChI=1S/C6H7NO/c7-5-2-1-3-6(8)4-5/h1-4,8H,7H2

1.8 InChIkey: CWLKGDAVCFYWJK-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC(=C1)O)N

1.10 Isomers Smiles: C1=CC(=CC(=C1)O)N

2. Properties

2.1 Density: 1.21

2.1 Melting point: 121-124℃

2.1 Boiling point: 253 to 259° F (NTP, 1992)

2.1 Refractive index: 1.5444 (estimate)

2.1 Flash Point: 155℃

2.1 Precise Quality: 109.05300

2.1 PSA: 46.25000

2.1 logP: 1.55560

2.1 Solubility: 26g/l

2.2 AnalyticLaboratory Methods: NEW DETECTION REAGENT FOR IDENTIFICATION & SEMIQUANTITATIVE DETERMINATION OF AMINOPHENOLS IN POLLUTED WATER; USING THIN LAYER CHROMATOGRAPHY IS PRESENTED. /AMINOPHENOLS/

2.3 Appearance: white crystals

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: Light grey crystal powder

2.6 Color/Form: White prisms from toluene or water
White crystals

2.7 Decomposition: When heated to decomposition it emits toxic fumes of /nitrogen oxides/.

2.8 Odor: odorless

2.9 PH: 6.8 (10g/l, H2O, 20℃)

2.10 Physical: PHYSICAL DESCRIPTION: White crystals or off-white flakes. (NTP, 1992)

2.11 pKa: 4.37, 9.82(at 20℃)

2.12 Water Solubility: 35 g/L (20 oC)

2.13 Spectral Properties: IR: 8088 (Sadtler Research Laboratories IR Grating Collection)
UV: 3509 (Sadtler Research Laboratories Spectral Collection)
NMR: 10220 (Sadtler Research Laboratories Spectral Collection)
MASS: 46 (Aldermaston, Eight Peak Index of Mass Spectra, UK)
Intense mass spectral peaks: 80 m/z, 109 m/z

2.14 Stability: Stable. Combustible. Incompatible with strong oxidizing agents, bases, mineral acids. May be light or air-sensitive.

2.15 StorageTemp: Store in a cool, dry place. Keep container closed when not in use.

3. Use and Manufacturing

3.1 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.

3.2 General Description: White crystals or off-white flakes.

3.3 GHS Classification: Signal: Warning
GHS Hazard Statements
H302: Harmful if swallowed [Warning Acute toxicity, oral]
H332: Harmful if inhaled [Warning Acute toxicity, inhalation]
H411: Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes
P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, and P501

3.4 Methods of Manufacturing: ... 3-Aminophenol; cannot be obtained easily by reduction. It is made mainly by the reaction of 3-aminobenzenesulfonic acid; with sodium hydroxide; or by the reaction of resorcinol; with ammonia;. Substitution of the sulfonic acid group in 3-aminobenzenesulfonic acid; is accomplished by caustic soda; fusion (5 - 6 hr; 240 - 245 deg C). The product is purified by vacuum distillation. Alternatively, resorcinol; reacts with ammonia;, for example, in the presence of diammonium phosphate; and arsenic pentoxide; or ammonium sulfite; to form 3-aminophenol;. The compound also may be made by hydrolysis of 3-aminoaniline;

3.5 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

3.6 Purification Methods: Crystallise it from hot water or toluene. [Beilstein 13 IV 952.]

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

3.8 Usage: 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.; View all

3.9 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. 3-Aminophenol Preparation Products And Raw materials Raw materials

4. Safety and Handling

4.1 Hazard Codes: Xn

4.1 Risk Statements: R20/22;R51/53

4.1 Safety Statements: S28;S61

4.1 Packing Group: III

4.1 Octanol/Water Partition Coefficient: log Kow= 0.21 at pH 5.6

4.2 Fire Hazard: Flash point data for 3-Aminophenol are not available. 3-Aminophenol is probably combustible.

4.3 Other Preventative Measures: SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. /Aminophenols/
Personnel protection: Avoid breathing dusts, and fumes from burning material. Keep upwind. Avoid bodily contact with the material. Do not handle broken packages unless wearing appropriate personal protective equipment. /Aminophenols/; View all

4.4 Hazard Class: 6.1

4.4 DisposalMethods: SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

4.5 DOT Emergency Guidelines: /GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Aminophenols/
GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Aminophenols/
GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number. As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Aminophenols/
GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Aminophenols/
GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Evacuation: Fire: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. /Aminophenols/
GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire: Small fires: Dry chemical, CO2 or water spray. Large fires: Water spray, fog or regular foam. Move containers from fire area if you can do it without risk. Dike fire control water for later disposal; do not scatter the material. Use water spray; do not use straight streams. Fire involving tanks or car/trailer loads: Fight fire from maximum distance or use unmanned hose holders or monitor nozzles. Do not get water inside containers. Cool containers with flooding quantities of water until well after fire is out. Withdraw immediately in case of rising sound from venting safety devices or discoloration of tank. ALWAYS stay away from tanks engulfed in fire. For massive fire, use unmanned hose holders or monitor nozzles; if this is impossible, withdraw from area and let fire burn. /Aminophenols/
GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Spill or Leak: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Cover with plastic sheet to prevent spreading . Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. /Aminophenols/
GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ First Aid: Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim warm and quiet. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. /Aminophenols/; View all

4.6 RIDADR: UN 2512

4.6 Fire Fighting Procedures: If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources. /Aminophenols/

4.7 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,.

4.8 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.

4.9 WGK Germany: 2

4.9 RTECS: SJ4900000

4.9 Protective Equipment and Clothing: A skin and eye irritant.

4.10 Skin, Eye, and Respiratory Irritations: A skin and eye irritant.

4.11 Safety: Hazard Codes:Xn,N
Risk Statements: 20/22-51/53
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: 28-61
S28:After contact with skin, wash immediately with plenty of soap-suds.
S61:Avoid release to the environment. Refer to special instructions / safety data sheets.
RIDADR: UN 2512 6.1/PG 3
WGK Germany: 2
RTECS: SJ4900000
F: 8-19
HazardClass: 6.1
PackingGroup: III

4.12 Specification: 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.
Fire Hazard : Flash point data for 3-Aminophenol are not available. 3-Aminophenol is probably combustible.
Classification Code of 3-Aminophenol (CAS NO.591-27-5 ) : Mutation data;Reproductive Effect;Skin / Eye Irritant

4.13 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
bird - wild	LD50	oral	237mg/kg (237mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
mammal (species unspecified)	LD50	unreported	1245mg/kg (1245mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 48(9), Pg. 19, 1983.
mouse	LD50	intraperitoneal	150mg/kg (150mg/kg)		National Technical Information Service. Vol. AD691-490,
mouse	LD50	oral	401mg/kg (401mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL:EXCITEMENT LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(1), Pg. 49, 1988.
mouse	LD50	unreported	225mg/kg (225mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(3), Pg. 4, 1985.
quail	LD50	oral	750mg/kg (750mg/kg)		Archives of Environmental Contamination and Toxicology. Vol. 12, Pg. 355, 1983.
rat	LC50	inhalation	1162mg/m3 (1162mg/m3)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(1), Pg. 49, 1988.
rat	LD50	oral	924mg/kg (924mg/kg)	PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE BEHAVIORAL: EXCITEMENT LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES	Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 32(1), Pg. 49, 1988.
rat	LD50	unreported	1125mg/kg (1125mg/kg)		Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 50(3), Pg. 4, 1985.
rat	LDLo	intraperitoneal	1gm/kg (1000mg/kg)		Archives Internationales de Pharmacodynamie et de Therapie. Vol. 131, Pg. 151, 1961.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

Acute toxicity - Inhalation, Category 4

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed H332 Harmful if inhaled H411 Toxic to aquatic life with long lasting effects
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P273 Avoid release to the environment.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P391 Collect spillage.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : in DMSO-d6

1H NMR : 400 MHz in DMSO-d6

IR : KBr disc

Mass

Mass spectrum (electron ionization)

UV/Visible spectrum

7. Synthesis Route

591-27-5Total: 43 Synthesis Route

65-49-6 161 Suppliers

591-27-5 230 Suppliers

Literatures:
Chemical and Pharmaceutical Bulletin, , vol. 30, # 2 p. 734 - 738
Yield: null

65-49-6 161 Suppliers

124-38-9 151 Suppliers

591-27-5 230 Suppliers

Literatures:
Journal of Pharmaceutical Sciences, , vol. 74, # 12 p. 1274 - 1282
Yield: null

626-02-8 110 Suppliers

591-27-5 230 Suppliers

Literatures:
Catalysis Communications, , vol. 32, p. 28 - 31
Yield: ~95%

View all

8. Precursor and Product

precursor:

536-90-3

5336-26-5

121-47-1

701-82-6

5220-49-5

554-84-7

51642-25-2

19962-06-2

626-02-8

65-49-6

720-97-8

1484-26-0

108-42-9

30418-59-8

619-19-2

108-46-3

108-45-2

621-42-1

619-17-0

View all

product :

5055-72-1

6317-89-1

5220-49-5

712-34-5

91-65-6

3743-28-0

3394-05-6

626-02-8

621-42-1

2476-29-1

3874-39-3

4787-77-3

5336-26-5

554-84-7

873-62-1

80-30-8

51-81-0

588-16-9

372-20-3

578-67-6

580-20-1

591-20-8

3125-63-1

1122-82-3

2050-15-9

View all

9. Other Information

9.0 Usage: A chemical used in the preparation of inhibitors of mammalian carbonic anhydrase isoforms. It is also used in the preparation of quinoline tethered fluorescent carbon dots for regulated anticancer discovery. It is employed in the production of TB drugs, salicylic acid, amino stabilizer and developers. 3-Aminophenol has been used as a stabilizer of chlorine-containing thermoplastics, although its principal use is as an intermediate in the production of 4-amino-2-hydroxybenzoic acid this isomer is also employed as a hair colorant and as a coupler molecule in hair dyes.

10. Computational chemical data

Molecular Weight: 109.128g/mol
Molecular Formula: C₆H₇NO
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 109.052763847
Monoisotopic Mass: 109.052763847
Complexity: 74.9
Rotatable Bond Count: 0
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 2
Topological Polar Surface Area: 46.2
Heavy Atom Count: 8
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADcYBiIAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgAQCAAACAyBkAAwxoBAAgCAACRCQACCAAAgIgAIiAAGbIgIJiKCkZOAcABm0BkI2AeQUAEAAAAAAgAAAAAAAAAEAAAAAAAAAAAAAA==

11. Question & Answer

What is 3-Aminophenol and how is it used? Feb 12 2023
3-Aminophenol, also known as m-Aminophenol, is a white crystalline substance that is soluble in water, ethanol, and ether, but insoluble in benzene and gasoline. It is commonly used as a dye and pharm..
What are the properties and uses of 2-Aminophenol and 3-Aminophenol? Dec 16 2019
2-Aminophenol is also known as ortho-aminophenol. CAS number: 95-55-6 Chemical formula: C6H7NO Appearance: White or light gray crystalline powder. Main uses: It is used in the production of dyes, pha..

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3-Aminophenol