53222-92-7

Basic information

• Product Name: 3-Amino-2-methylphenol
• Synonyms: 3-HYDROXY-2-METHYLANILINE;3-AMINO-O-CRESOL;3-AMINO-2-METHYLPHENOL;2-METHYL-3-HYDROXY ANILINE;2-amino-o-cresol;2-Amino-6-hydroxytoluene;3-Amino-o-cresol,95%;3-Amino-2-methylphenol,3-Amino-o-cresol
• CAS NO: 53222-92-7
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• EINECS: 258-438-5
• Mol File: 53222-92-7.mol
• Article Data: 12

Chemical Properties

• Melting Point: 129-130 °C(lit.)
• Boiling Point: 229.26°C (rough estimate)
• Flash Point: 115.4°C
• Appearance: /Solid
• Density: 1.0877 (rough estimate)
• Vapor Pressure: 0.0217mmHg at 25°C
• Refractive Index: 1.5380 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: soluble in Methanol
• PKA: 10.36±0.10(Predicted)
• CAS DataBase Reference: 3-Amino-2-methylphenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Amino-2-methylphenol(53222-92-7)
• EPA Substance Registry System: 3-Amino-2-methylphenol(53222-92-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 53222-92-7(Hazardous Substances Data)

Usage

Description

3-Amino-2-methylphenol, also known as methylcatechol, is an organic compound with the molecular formula C7H9NO. It is a derivative of phenol, featuring an amino group and a methyl group attached to the benzene ring. 3-Amino-2-methylphenol is known for its chemical reactivity and is a key intermediate in the synthesis of various polymers and other chemical products.

Uses

Used in Chemical Synthesis:
3-Amino-2-methylphenol is used as a key intermediate in the production of various chemical compounds and polymers. Its versatile structure allows for the creation of a wide range of materials with different properties and applications.
Used in Polymer Industry:
3-Amino-2-methylphenol is used as a monomer for the synthesis of (Diimido)dicarboxylic Acid, which is a crucial component in the production of high-performance polymers such as Imide, Polyamic Acid, Polyamides, Polyesters, and Polyureas. These polymers find applications in various industries, including automotive, electronics, textiles, and packaging, due to their excellent mechanical, thermal, and chemical properties.
Used in Pharmaceutical Industry:
3-Amino-2-methylphenol can also be used as a building block for the synthesis of various pharmaceutical compounds, taking advantage of its reactive amino and phenolic groups. This allows for the development of new drugs with potential therapeutic applications.
Used in Dye and Pigment Industry:
Due to its chemical structure, 3-Amino-2-methylphenol can be used in the production of dyes and pigments, contributing to the colorants used in various applications such as printing, painting, and textiles.

InChI:InChI=1/C7H11NO/c1-7(8)5-3-2-4-6(7)9/h2-6,9H,8H2,1H3

Synthetic route

3-nitro-o-cresol (5460-31-1) → amino-6 hydroxy-2 toluene (53222-92-7)

Conditions	Yield
palladium on charcoal In ethanol	100%
palladium on charcoal In ethanol	100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;	99%

o-toluidine (95-53-4) → 3-amino-4-methylphenol (2836-00-2) + amino-6 hydroxy-2 toluene (53222-92-7)

Conditions	Yield
With dihydrogen peroxide; antimony pentafluoride In hydrogen fluoride at -20℃; for 0.25h; Mechanism; Product distribution;	A 21% B 42%
With dihydrogen peroxide; antimony pentafluoride In hydrogen fluoride at -20℃; for 0.25h;	A 21% B 42%

3-nitro-o-tolylamine (603-83-8) → amino-6 hydroxy-2 toluene (53222-92-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: Diazotization 2: tin; tin dichloride; hydrochloric acid / auf dem Wasserbade View Scheme
Multi-step reaction with 2 steps 1: concentrated sulfuric acid; water; sodium nitrite / Diazotization 2: sodium disulfite View Scheme

2,6-dinitrotoluene (606-20-2) → amino-6 hydroxy-2 toluene (53222-92-7)

Conditions	Yield
Multi-step reaction with 3 steps 1: alcohol; hydrogen sulfide; ammoniacal 2: concentrated sulfuric acid; water; sodium nitrite / Diazotization 3: sodium disulfite View Scheme

amino-6 hydroxy-2 toluene (53222-92-7) + (S)-tert-butyl 3-((4-(2-fluoropyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate → (S)-tert-butyl 3-((4-(2-(3-amino-2-methylphenoxy)pyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 1h; Sealed tube;	100%

1-(tert-butoxycarbonyl)-L-proline (15761-39-4) + amino-6 hydroxy-2 toluene (53222-92-7) → (S)-tert-butyl 2-((3-hydroxy-2-methylphenyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h;	99%
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 5h;

5-bromo-1,3-xylene (556-96-7) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-[(3,5-dimethylphenyl)amino]-2-methylphenol (1198117-45-1)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1h; Inert atmosphere;	94%

para-bromotoluene (106-38-7) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-[(4-methylphenyl)amino]-2-methylphenol (1198117-51-9)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1h; Inert atmosphere;	92%

carbon monoxide (201230-82-2) + para-iodoanisole (696-62-8) + amino-6 hydroxy-2 toluene (53222-92-7) → 4-methoxybenzoic acid 3-amino-2-methylphenyl ester

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate In acetonitrile at 100℃; under 10343.2 Torr; for 15h; chemoselective reaction;	92%

para-chlorotoluene (106-43-4) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-[(4-methylphenyl)amino]-2-methylphenol (1198117-51-9)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1.16667h; Inert atmosphere;	91%

amino-6 hydroxy-2 toluene (53222-92-7) + 6,7-dimethoxy-4-chloroquinazoline (13790-39-1) → 3-((6,7-dimethoxyquinazolin-4-yl)amino)-2-methylphenol hydrochloride

Conditions	Yield
In isopropyl alcohol Heating;	91%

1-bromo-4-methoxy-benzene (104-92-7) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-[(4-methoxyphenyl)amino]-2-methylphenol (1198117-47-3)

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2',4',6'-triisopropyl-1,1'-biphenyl][2-(2-aminoethyl)phenyl]palladium(ll); sodium t-butanolate In 1,4-dioxane at 90℃; for 1h; Inert atmosphere;	86%

3,5-dimethylphenyl iodide (22445-41-6) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-(3,5-dimethylphenoxy)-2-methylphenylamine (1198117-43-9)

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;	86%

styrene (100-42-5) + carbon monoxide (201230-82-2) + amino-6 hydroxy-2 toluene (53222-92-7) → N-(3-hydroxy-2-methylphenyl)-2-phenylpropanamide

Conditions	Yield
With 5-chloro-2-hydroxybenzoic acid; 1,3,5,7-tetramethyl-2,4,8-trioxa-6-phenyl-6-phosphaadamantane; boric acid; palladium dichloride In butanone at 120℃; under 15001.5 Torr; for 24h; Autoclave; regioselective reaction;	86%

di-tert-butyl dicarbonate (24424-99-5) + amino-6 hydroxy-2 toluene (53222-92-7) → tert-butyl (3-hydroxy-2-methylphenyl)carbamate

Conditions	Yield
In dichloromethane at 70℃; for 12h; Inert atmosphere;	83.1%

para-iodoanisole (696-62-8) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-(4-methoxyphenoxy)-2-methyl-phenylamine (1198117-46-2)

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;	80%

amino-6 hydroxy-2 toluene (53222-92-7) → (2-methyl-3-aminophenoxy)acetonitrile

Conditions	Yield
With caesium carbonate In methylethylketone (MEK); cyanomethyl bromide	79%
With caesium carbonate In methylethylketone (MEK); cyanomethyl bromide	79%

4-tolyl iodide (624-31-7) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-(4-methylphenoxy)-2-methylphenylamine (1198117-49-5)

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;	78%

carbon monoxide (201230-82-2) + para-iodoanisole (696-62-8) + amino-6 hydroxy-2 toluene (53222-92-7) → 4-methoxybenzoic acid 3-amino-2-methylphenyl ester + C15H15NO3

Conditions	Yield
With palladium diacetate; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis-(diisobutylphosphino)propane In acetonitrile at 100℃; under 10343.2 Torr; for 15h; chemoselective reaction;	A 6% B 75%

para-iodoanisole (696-62-8) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-[(4-methoxyphenyl)amino]-2-methylphenol (1198117-47-3)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium tert-butylate In 1,4-dioxane at 120℃;	71%

ammonium hydroxide (1336-21-6) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-amino-4-chloro-2-methyl-phenol

Conditions	Yield
With N-chloro-succinimide In methanesulfonic acid; water	70.5%
With N-chloro-succinimide In methanesulfonic acid; water	70.5%

phenyl N-[4-(trifluoromethyl)-1,3-thiazol-2-yl]carbamate (625119-98-4) + amino-6 hydroxy-2 toluene (53222-92-7) → N-(3-hydroxy-2-methylphenyl)-N'-[4-(trifluoromethyl)-1,3-thiazol-2-yl]urea

Conditions	Yield
Stage #1: phenyl N-[4-(trifluoromethyl)-1,3-thiazol-2-yl]carbamate; amino-6 hydroxy-2 toluene Stage #2: In methanol at 35 - 40℃; for 0.333333h; Stage #3: With ammonia In methanol; water	67%

amino-6 hydroxy-2 toluene (53222-92-7) + acetic anhydride (108-24-7) → N-(3-hydroxy-2-methylphenyl)acetamide (76064-17-0)

Conditions	Yield
In water at 20℃; Sonication; Heating;	62%
In water at 20 - 50℃; Sonication;	62%
With sodium hydroxide; acetic acid

N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide (1005787-88-1) + amino-6 hydroxy-2 toluene (53222-92-7) → N-[6-(3-amino-2-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide (1005780-11-9)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide	58%
With potassium carbonate In N,N-dimethyl-formamide at 180℃; Microwave irradiation;	58%

amino-6 hydroxy-2 toluene (53222-92-7) → 3-amino-4-chloro-2-methyl-phenol

Conditions	Yield
With N-chloro-succinimide; methanesulfonic acid at 10 - 12℃;	54.5%

Methyl isobutyl carbinol (108-11-2) + amino-6 hydroxy-2 toluene (53222-92-7) → 2-methyl-3-[(4-methylpentan-2-yl)oxy]aniline

Conditions	Yield
With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine In tetrahydrofuran for 16h;	54%

amino-6 hydroxy-2 toluene (53222-92-7) → 3-iodo-2-methyl-phenol (116529-75-0)

Conditions	Yield
Stage #1: amino-6 hydroxy-2 toluene With tetrafluoroboric acid-diethyl ether complex; isopentyl nitrite In tetrahydrofuran at -10 - 0℃; for 0.5h; Stage #2: With sodium iodide In acetone at 20℃; for 12h;	52%

trans-Crotonaldehyde (123-73-9) + amino-6 hydroxy-2 toluene (53222-92-7) → 2,8-dimethylquinolin-7-ol (1412256-52-0)

Conditions	Yield
With hydrogenchloride In water for 2h; Reflux;	51%

amino-6 hydroxy-2 toluene (53222-92-7) + chloroformic acid ethyl ester (541-41-3) → 2-Methyl-3-carbethoxyaminophenol (129503-07-7)

Conditions	Yield
In diethyl ether for 2h; Ambient temperature;	50%

(2S)-2-benzyl-oxirane-2-carboxylic acid (910539-51-4) + amino-6 hydroxy-2 toluene (53222-92-7) → (2S)-2-benzyl-oxirane-2-carboxylic acid (3-hydroxy-2-methyl-phenyl)-amide (910539-80-9)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; diisopropylamine In dichloromethane at 20℃;	46%

amino-6 hydroxy-2 toluene (53222-92-7) + 4-chloro-3-nitro-2-pyridinamine (6980-08-1) → 4-(3-amino-2-methylphenoxy)-3-nitropyridin-2-amine (956488-64-5)

Conditions	Yield
Stage #1: amino-6 hydroxy-2 toluene With potassium tert-butylate In N,N-dimethyl-formamide at 20℃; for 1h; Inert atmosphere; Stage #2: 4-chloro-3-nitro-2-pyridinamine In N,N-dimethyl-formamide at 80℃; for 20h; Inert atmosphere; Further stages;	28%

3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (765962-75-2) + amino-6 hydroxy-2 toluene (53222-92-7) → 3-(3-amino-2-methylphenoxy)-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline (1295567-68-8)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 16h;	26%

Upstream product

• 5460-31-1 3-nitro-o-cresol 
• 606-20-2 2,6-dinitrotoluene 
• 603-83-8 3-nitro-o-tolylamine 
• 95-53-4 o-toluidine 

Downstream Products

• 125709-97-9 4,8-dimethyl-3H-phenoxazin-3-one 
• 125709-91-3 2-hydroxy-5-methyl-N-(2'-hydroxy-5'-methylphenyl)benzoquinone monoimine 
• 125709-92-4 N-(2'-hydroxy-5'-methylphenyl)-2,8-dimethyl-3H-phenoxazin-3-onimine 
• 125732-06-1 2,9-dimethyl-5a,6-dihydro-5a-methyltriphendioxazine 
• 1108169-70-5 8-chloro-2-{[(3-hydroxy-2-methylphenyl)amino]methyl}[1]benzothieno[3,2-d]pyrimidin-4(3H)-one 
• 116529-75-0 3-iodo-2-methyl-phenol 
• 1400704-09-7 (S)-2-({2-[3-(3-hydroxy-2-methyl-phenyl)prop-2-ynylamino]-4,6-dimethyl-pyrimidine-5-carbonyl}amino)-3-[(thiophene-2-carbonyl)amino]propionic acid methyl ester 
• 1400704-10-0 (S)-2-({2-[3-(3-hydroxy-2-methyl-phenyl)propylamino]-4,6-dimethyl-pyrimidine-5-carbonyl}amino)-3-[(thiophene-2-carbonyl)amino]propionic acid methyl ester 
• 52601-70-4 8-methyl-1,2,3,4-tetrahydroquinoline 

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