Product Name

  • Name

    3-Amino-2-methylphenol

  • EINECS 258-438-5
  • CAS No. 53222-92-7
  • Article Data16
  • CAS DataBase
  • Density 1.157g/cm3
  • Solubility
  • Melting Point 127-133 ºC
  • Formula C7H9 N O
  • Boiling Point 267.1°Cat760mmHg
  • Molecular Weight 123.155
  • Flash Point 115.4°C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes R36/37/38   
  • Molecular Structure Molecular Structure of 53222-92-7 (3-Amino-2-methylphenol)
  • Hazard Symbols
  • Synonyms o-Cresol,3-amino- (6CI); 2-Amino-6-hydroxytoluene; 2-Methyl-3-aminophenol;3-Amino-2-methylphenol; 3-Amino-o-cresol; 3-Hydroxy-2-methylaniline
  • PSA 46.25000
  • LogP 1.86400

Synthetic route

3-nitro-o-cresol
5460-31-1

3-nitro-o-cresol

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

Conditions
ConditionsYield
palladium on charcoal In ethanol100%
palladium on charcoal In ethanol100%
With palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 24h;99%
o-toluidine
95-53-4

o-toluidine

A

3-amino-4-methylphenol
2836-00-2

3-amino-4-methylphenol

B

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

Conditions
ConditionsYield
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

3-nitro-o-tolylamine

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

Conditions
ConditionsYield
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

2,6-dinitrotoluene

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

Conditions
ConditionsYield
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

amino-6 hydroxy-2 toluene

(S)-tert-butyl 3-((4-(2-fluoropyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate

(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

(S)-tert-butyl 3-((4-(2-(3-amino-2-methylphenoxy)pyridin-3-yl)pyrimidin-2-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With caesium carbonate In dimethyl sulfoxide at 120℃; for 1h; Sealed tube;100%
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

(S)-tert-butyl 2-((3-hydroxy-2-methylphenyl)carbamoyl)pyrrolidine-1-carboxylate

(S)-tert-butyl 2-((3-hydroxy-2-methylphenyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
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

5-bromo-1,3-xylene

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-[(3,5-dimethylphenyl)amino]-2-methylphenol
1198117-45-1

3-[(3,5-dimethylphenyl)amino]-2-methylphenol

Conditions
ConditionsYield
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

para-bromotoluene

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-[(4-methylphenyl)amino]-2-methylphenol
1198117-51-9

3-[(4-methylphenyl)amino]-2-methylphenol

Conditions
ConditionsYield
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

carbon monoxide

para-iodoanisole
696-62-8

para-iodoanisole

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

4-methoxybenzoic acid 3-amino-2-methylphenyl ester

4-methoxybenzoic acid 3-amino-2-methylphenyl ester

Conditions
ConditionsYield
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; potassium carbonate In acetonitrile at 100℃; under 10343.2 Torr; for 15h; chemoselective reaction;92%
...Expand
para-chlorotoluene
106-43-4

para-chlorotoluene

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-[(4-methylphenyl)amino]-2-methylphenol
1198117-51-9

3-[(4-methylphenyl)amino]-2-methylphenol

Conditions
ConditionsYield
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

amino-6 hydroxy-2 toluene

6,7-dimethoxy-4-chloroquinazoline
13790-39-1

6,7-dimethoxy-4-chloroquinazoline

3-((6,7-dimethoxyquinazolin-4-yl)amino)-2-methylphenol hydrochloride

3-((6,7-dimethoxyquinazolin-4-yl)amino)-2-methylphenol hydrochloride

Conditions
ConditionsYield
In isopropyl alcohol Heating;91%
1-bromo-4-methoxy-benzene
104-92-7

1-bromo-4-methoxy-benzene

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-[(4-methoxyphenyl)amino]-2-methylphenol
1198117-47-3

3-[(4-methoxyphenyl)amino]-2-methylphenol

Conditions
ConditionsYield
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

3,5-dimethylphenyl iodide

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-(3,5-dimethylphenoxy)-2-methylphenylamine
1198117-43-9

3-(3,5-dimethylphenoxy)-2-methylphenylamine

Conditions
ConditionsYield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;86%
styrene
100-42-5

styrene

carbon monoxide
201230-82-2

carbon monoxide

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

N-(3-hydroxy-2-methylphenyl)-2-phenylpropanamide

N-(3-hydroxy-2-methylphenyl)-2-phenylpropanamide

Conditions
ConditionsYield
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%
...Expand
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

tert-butyl (3-hydroxy-2-methylphenyl)carbamate

tert-butyl (3-hydroxy-2-methylphenyl)carbamate

Conditions
ConditionsYield
In dichloromethane at 70℃; for 12h; Inert atmosphere;83.1%
para-iodoanisole
696-62-8

para-iodoanisole

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-(4-methoxyphenoxy)-2-methyl-phenylamine
1198117-46-2

3-(4-methoxyphenoxy)-2-methyl-phenylamine

Conditions
ConditionsYield
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

amino-6 hydroxy-2 toluene

(2-methyl-3-aminophenoxy)acetonitrile

(2-methyl-3-aminophenoxy)acetonitrile

Conditions
ConditionsYield
With caesium carbonate In methylethylketone (MEK); cyanomethyl bromide79%
With caesium carbonate In methylethylketone (MEK); cyanomethyl bromide79%
4-tolyl iodide
624-31-7

4-tolyl iodide

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-(4-methylphenoxy)-2-methylphenylamine
1198117-49-5

3-(4-methylphenoxy)-2-methylphenylamine

Conditions
ConditionsYield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;78%
carbon monoxide
201230-82-2

carbon monoxide

para-iodoanisole
696-62-8

para-iodoanisole

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

A

4-methoxybenzoic acid 3-amino-2-methylphenyl ester

4-methoxybenzoic acid 3-amino-2-methylphenyl ester

B

C15H15NO3

C15H15NO3

Conditions
ConditionsYield
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%
...Expand
para-iodoanisole
696-62-8

para-iodoanisole

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-[(4-methoxyphenyl)amino]-2-methylphenol
1198117-47-3

3-[(4-methoxyphenyl)amino]-2-methylphenol

Conditions
ConditionsYield
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

ammonium hydroxide

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-amino-4-chloro-2-methyl-phenol

3-amino-4-chloro-2-methyl-phenol

Conditions
ConditionsYield
With N-chloro-succinimide In methanesulfonic acid; water70.5%
With N-chloro-succinimide In methanesulfonic acid; water70.5%
phenyl N-[4-(trifluoromethyl)-1,3-thiazol-2-yl]carbamate
625119-98-4

phenyl N-[4-(trifluoromethyl)-1,3-thiazol-2-yl]carbamate

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

N-(3-hydroxy-2-methylphenyl)-N'-[4-(trifluoromethyl)-1,3-thiazol-2-yl]urea

N-(3-hydroxy-2-methylphenyl)-N'-[4-(trifluoromethyl)-1,3-thiazol-2-yl]urea

Conditions
ConditionsYield
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

amino-6 hydroxy-2 toluene

acetic anhydride
108-24-7

acetic anhydride

N-(3-hydroxy-2-methylphenyl)acetamide
76064-17-0

N-(3-hydroxy-2-methylphenyl)acetamide

Conditions
ConditionsYield
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

N-(6-iodoimidazo[1,2-b]pyridazin-2-yl)cyclopropanecarboxamide

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

N-[6-(3-amino-2-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide
1005780-11-9

N-[6-(3-amino-2-methylphenoxy)imidazo[1,2-b]pyridazin-2-yl]cyclopropanecarboxamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide58%
With potassium carbonate In N,N-dimethyl-formamide at 180℃; Microwave irradiation;58%
amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-amino-4-chloro-2-methyl-phenol

3-amino-4-chloro-2-methyl-phenol

Conditions
ConditionsYield
With N-chloro-succinimide; methanesulfonic acid at 10 - 12℃;54.5%
Methyl isobutyl carbinol
108-11-2

Methyl isobutyl carbinol

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

2-methyl-3-[(4-methylpentan-2-yl)oxy]aniline

2-methyl-3-[(4-methylpentan-2-yl)oxy]aniline

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triethylamine; triphenylphosphine In tetrahydrofuran for 16h;54%
amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-iodo-2-methyl-phenol
116529-75-0

3-iodo-2-methyl-phenol

Conditions
ConditionsYield
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

trans-Crotonaldehyde

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

2,8-dimethylquinolin-7-ol
1412256-52-0

2,8-dimethylquinolin-7-ol

Conditions
ConditionsYield
With hydrogenchloride In water for 2h; Reflux;51%
amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

2-Methyl-3-carbethoxyaminophenol
129503-07-7

2-Methyl-3-carbethoxyaminophenol

Conditions
ConditionsYield
In diethyl ether for 2h; Ambient temperature;50%
(2S)-2-benzyl-oxirane-2-carboxylic acid
910539-51-4

(2S)-2-benzyl-oxirane-2-carboxylic acid

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

(2S)-2-benzyl-oxirane-2-carboxylic acid (3-hydroxy-2-methyl-phenyl)-amide
910539-80-9

(2S)-2-benzyl-oxirane-2-carboxylic acid (3-hydroxy-2-methyl-phenyl)-amide

Conditions
ConditionsYield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; diisopropylamine In dichloromethane at 20℃;46%
amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

4-chloro-3-nitro-2-pyridinamine
6980-08-1

4-chloro-3-nitro-2-pyridinamine

4-(3-amino-2-methylphenoxy)-3-nitropyridin-2-amine
956488-64-5

4-(3-amino-2-methylphenoxy)-3-nitropyridin-2-amine

Conditions
ConditionsYield
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

3,5-difluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline

amino-6 hydroxy-2 toluene
53222-92-7

amino-6 hydroxy-2 toluene

3-(3-amino-2-methylphenoxy)-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline
1295567-68-8

3-(3-amino-2-methylphenoxy)-5-fluoro-N-(2-fluoro-4-iodophenyl)-2-nitroaniline

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

3-Amino-2-methylphenol Chemical Properties

Molecular Structure:

Molecular Formula: C7H9NO
Molecular Weight: 123.1525
IUPAC Name: 3-Amino-2-methylphenol
Synonyms of 2-Amino-o-cresol (CAS NO.53222-92-7): EINECS 258-438-5 ; 3-Amino-o-cresol ; 2-Methyl-3-hydroxy aniline ; 2-Amino-o-cresol ; 2-Amino-6-hydroxytoluene ; 3-Amino-o-cresol,95%
CAS NO: 53222-92-7
Melting point: 129-130 °C 
Index of Refraction: 1.616
Molar Refractivity: 37.19 cm3
Molar Volume: 106.4 cm3
Surface Tension: 51.9 dyne/cm
Density: 1.157 g/cm3
Flash Point: 115.4 °C
Enthalpy of Vaporization: 52.55 kJ/mol
Boiling Point: 267.1 °C at 760 mmHg
Vapour Pressure: 0.00504 mmHg at 25°C

3-Amino-2-methylphenol Safety Profile

Hazard Codes of 2-Amino-o-cresol (CAS NO.53222-92-7): IrritantXi
Risk Statements: 36/37/38 
R36/37/38: Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S37/39: Wear suitable gloves and eye/face protection.
WGK Germany: 3

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