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53222-92-7

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53222-92-7 Usage

Uses

3-Amino-2-methylphenol is used in production of (Diimido)dicarboxylic Acid, Imide, Polyamic Acid, Polyamides, Polyesters, and Polyureas.

Check Digit Verification of cas no

The CAS Registry Mumber 53222-92-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,2,2 and 2 respectively; the second part has 2 digits, 9 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 53222-92:
(7*5)+(6*3)+(5*2)+(4*2)+(3*2)+(2*9)+(1*2)=97
97 % 10 = 7
So 53222-92-7 is a valid CAS Registry Number.
InChI:InChI=1/C7H11NO/c1-7(8)5-3-2-4-6(7)9/h2-6,9H,8H2,1H3

53222-92-7 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Alfa Aesar

  • (H66554)  3-Amino-2-methylphenol, 98%   

  • 53222-92-7

  • 1g

  • 267.0CNY

  • Detail
  • Alfa Aesar

  • (H66554)  3-Amino-2-methylphenol, 98%   

  • 53222-92-7

  • 5g

  • 1000.0CNY

  • Detail
  • Alfa Aesar

  • (H66554)  3-Amino-2-methylphenol, 98%   

  • 53222-92-7

  • 25g

  • 4008.0CNY

  • Detail

53222-92-7Synthetic 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%
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%
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%
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%

53222-92-7Relevant articles and documents

Highly efficient catalysts for the hydrogenation of nitro-substituted aromatics

Raja, Robert,Golovko, Vladimir B.,Thomas, John M.,Berenguer-Murcia, Angel,Zhou, Wuzong,Xie, Songhai,Johnson, Brian F. G.

, p. 2026 - 2028 (2005)

Nanoparticles of Co and NiPd, derived from colloidal precursors and supported on commercially available non-ordered mesoporous silica, are highly effective, cheap, recyclable and industrially viable catalysts for the hydrogenation of a range of nitro-substituted aromatics under mild conditions. The Royal Society of Chemistry 2005.

New potent biaryl sulfate-based hepatitis C virus inhibitors

You, Youngsu,Kim, Hee Sun,Bae, Il Hak,Lee, Seung Gi,Jee, Min Hyeok,Keum, Gyochang,Jang, Sung Key,Kim, B. Moon

, p. 87 - 100 (2016/09/23)

The discovery of a new series of potent hepatitis C virus (HCV) NS5A inhibitors containing biaryl sulfone or sulfate cores is reported. Structure-activity relationship (SAR) studies on inhibitors containing various substitution patterns of the sulfate or sulfone core structure established that m-,m′- substituted biaryl sulfate core-based inhibitors containing an amide moiety (compound 20) or an imidazole moiety (compound 24) showed extremely high potency. Compound 20 demonstrated double-digit pM potencies against both genotype 1b (GT-1b) and 2a (GT-2a). Compound 24 also exhibited double-digit pM potencies against GT-1b and sub nM potencies against GT-2a. Furthermore, compounds 20 and 24 exhibited no cardiotoxicity in an hERG ligand binding assay and showed acceptable plasma stability and no mutagenic potential in the Ames test. In addition, these compounds showed distinctive additive effects in combination treatment with the NS5B targeting drug sofosbuvir (Sovaldi). The results of this study showed that the compounds 20 and 24 could be effective HCV inhibitors.

Synthesis and biological evaluation of arylated novobiocin analogs as Hsp90 inhibitors

Kusuma, Bhaskar Reddy,Duerfeldt, Adam S.,Blagg, Brian S.J.

scheme or table, p. 7170 - 7174 (2012/01/15)

Novobiocin analogs lacking labile glycosidic ether have been designed, synthesized and evaluated for Hsp90 inhibitory activity. Replacement of the synthetically complex noviose sugar with simple aromatic side chains produced analogs that maintain moderate cytotoxic activity against MCF7 and SkBR3 breast cancer cell-lines. Rationale for the preparation of des-noviose novobiocin analogs in addition to their synthesis and biological evaluation are presented herein.

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