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52273-77-5

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52273-77-5 Usage

Description

2-(3-Aminophenyl)ethanol is an organic compound that features a phenyl group with an amino substituent at the 3-position and an ethanol chain attached to the 2-position. It is a versatile building block in organic synthesis and possesses a combination of functional groups that make it a valuable intermediate for various chemical reactions.

Uses

Used in Pharmaceutical Industry:
2-(3-Aminophenyl)ethanol is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its unique structure allows for the creation of a wide range of molecules with potential therapeutic applications.
Used in Chemical Synthesis:
2-(3-Aminophenyl)ethanol is used as a key building block in the synthesis of complex organic molecules, such as indolines and dihydrobenzofurans, through iron and copper-catalyzed iodination and cyclization reactions. These synthesized compounds can be further utilized in the development of new drugs, materials, and other specialty chemicals.
Used in Research and Development:
2-(3-Aminophenyl)ethanol serves as a valuable research tool in the field of organic chemistry, enabling scientists to explore new reaction pathways and develop innovative synthetic methods. Its unique structure and reactivity make it an attractive candidate for studying various chemical transformations and understanding the underlying mechanisms.

Check Digit Verification of cas no

The CAS Registry Mumber 52273-77-5 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,2,2,7 and 3 respectively; the second part has 2 digits, 7 and 7 respectively.
Calculate Digit Verification of CAS Registry Number 52273-77:
(7*5)+(6*2)+(5*2)+(4*7)+(3*3)+(2*7)+(1*7)=115
115 % 10 = 5
So 52273-77-5 is a valid CAS Registry Number.
InChI:InChI=1/C8H11NO/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6,10H,4-5,9H2

52273-77-5SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 16, 2017

Revision Date: Aug 16, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-(3-Aminophenyl)ethanol

1.2 Other means of identification

Product number -
Other names 3-aminophenylethyl alcohol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:52273-77-5 SDS

52273-77-5Synthetic route

2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
With palladium on carbon (10%) In tetrahydrofuran Cooling with ice; Inert atmosphere;100%
With hydrogen; palladium 10% on activated carbon In methanol under 2327.23 Torr;99%
With palladium 10% on activated carbon; hydrogen In ethanol at 20℃; for 1.5h;98%
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
In ethanol; water100%
(3-amino-phenyl)-acetic acid ethyl ester
52273-79-7

(3-amino-phenyl)-acetic acid ethyl ester

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride In 1,4-dioxane Ambient temperature;40%
3-amino phenylacetic acid
14338-36-4

3-amino phenylacetic acid

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
With lithium aluminium tetrahydride
2-(4-amino-3-nitrophenyl)ethanol
15896-61-4

2-(4-amino-3-nitrophenyl)ethanol

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NaNO2; aqueous HCl / anschliessendes Behandeln mit H3PO2
2: SnCl2; aqueous HCl
View Scheme
4-acetamido-3-nitrophenethyl acetate
92959-73-4

4-acetamido-3-nitrophenethyl acetate

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: aqueous HCl
2: NaNO2; aqueous HCl / anschliessendes Behandeln mit H3PO2
3: SnCl2; aqueous HCl
View Scheme
2-(3-nitrophenyl)ethanol
52022-77-2

2-(3-nitrophenyl)ethanol

pyrographite
7440-44-0

pyrographite

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
In ethanol
(3-nitrophenyl)acetonitrile
621-50-1

(3-nitrophenyl)acetonitrile

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: acetic acid; sulfuric acid / water / 110 °C
2: dimethylsulfide borane complex / tetrahydrofuran / Reflux
3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid; acetic acid / water / 110 °C
2: dimethylsulfide borane complex / tetrahydrofuran / Reflux
3: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
View Scheme
3-nitro-benzeneacetic acid
1877-73-2

3-nitro-benzeneacetic acid

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex / tetrahydrofuran / Reflux
2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: dimethylsulfide borane complex / tetrahydrofuran / Reflux
2: palladium 10% on activated carbon; hydrogen / ethanol / 20 °C
View Scheme
carbonochloridic acid 1-chloro-ethyl ester
50893-53-3

carbonochloridic acid 1-chloro-ethyl ester

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

chloroethyl carbamate

chloroethyl carbamate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water100%
5-chloro-1H-Indole-2-carboxylic acid
10517-21-2

5-chloro-1H-Indole-2-carboxylic acid

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

C17H15ClN2O2
1036750-34-1

C17H15ClN2O2

Conditions
ConditionsYield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 14h;97%
2,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine
1236130-76-9

2,5-dichloro-N-[2-(3-methoxyphenyl)ethyl]pyrimidin-4-amine

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

2-{3-[(5-chloro-4-{[2-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol
1236130-79-2

2-{3-[(5-chloro-4-{[2-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane at 100℃; for 16h;96%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline
183322-18-1

4-chloro-6,7-bis(2-methoxyethoxy)quinazoline

2-(3-((6,7-bis(2-methoxyethoxy)quinazolin-4-yl)amino)phenyl)ethan-1-ol

2-(3-((6,7-bis(2-methoxyethoxy)quinazolin-4-yl)amino)phenyl)ethan-1-ol

Conditions
ConditionsYield
With pyridine In isopropyl alcohol for 4h; Reflux; Inert atmosphere;96%
2,5-dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine
1236130-81-6

2,5-dichloro-N-[3-(3-methoxyphenyl)propyl]pyrimidin-4-amine

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

2-{3-[(5-chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol
1236130-89-4

2-{3-[(5-chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane at 100℃; for 16h;92%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

tert-butyl N-[3-(2-hydroxyethyl)phenyl]carbamate
180002-10-2

tert-butyl N-[3-(2-hydroxyethyl)phenyl]carbamate

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane; water at 20℃;79%
With sodium hydroxide In 1,4-dioxane; water at 20℃;79%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

phenylcarbonochloridothioate
1005-56-7

phenylcarbonochloridothioate

2-(3-((phenoxythioxomethyl)amino)phenyl)ethan-1-ol
366492-72-0

2-(3-((phenoxythioxomethyl)amino)phenyl)ethan-1-ol

Conditions
ConditionsYield
In tetrahydrofuran at 20℃; for 0.5h;77%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

ortho-nitrofluorobenzene
1493-27-2

ortho-nitrofluorobenzene

2-(3-((2-nitrophenyl)amino)phenyl)ethanol
1429642-71-6

2-(3-((2-nitrophenyl)amino)phenyl)ethanol

Conditions
ConditionsYield
With triethylamine at 110℃; for 15h; Sealed tube;77%
2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine
1236130-57-6

2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

2-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol
1236130-60-1

2-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol

Conditions
ConditionsYield
With toluene-4-sulfonic acid In 1,4-dioxane at 105℃; for 3h;74%
2,4-dimethyl-thiazole-5-carboxylic acid
53137-27-2

2,4-dimethyl-thiazole-5-carboxylic acid

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

N-[3-(2-hydroxyethyl)phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide
844904-20-7

N-[3-(2-hydroxyethyl)phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) for 14h;73%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

2-(3-iodophenyl)ethan-1-ol
127201-31-4

2-(3-iodophenyl)ethan-1-ol

Conditions
ConditionsYield
Stage #1: 2-(3-aminophenyl)ethan-1-ol With sulfuric acid; sodium nitrite In water at 0℃; for 0.5h;
Stage #2: With potassium iodide In water at 0 - 60℃; for 2.5h;
67%
9-chloro-3-methoxyacridine
16492-14-1

9-chloro-3-methoxyacridine

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

9-[3'-(β-hydroxyethyl)anilino]-3-methoxyacridine
135785-71-6

9-[3'-(β-hydroxyethyl)anilino]-3-methoxyacridine

Conditions
ConditionsYield
With methanesulfonic acid In methanol65%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

BrH*C8H10BrN
914605-41-7

BrH*C8H10BrN

Conditions
ConditionsYield
With hydrogen bromide In water at 90℃; for 18h;61%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

acrylic acid methyl ester
292638-85-8

acrylic acid methyl ester

methyl 2-chloro-3-[3-(2-hydroxyethyl)phenyl]propanoate
817642-95-8

methyl 2-chloro-3-[3-(2-hydroxyethyl)phenyl]propanoate

Conditions
ConditionsYield
Stage #1: 2-(3-aminophenyl)ethan-1-ol With hydrogenchloride; sodium nitrite In water; acetone at 0℃; for 1h;
Stage #2: acrylic acid methyl ester; copper(l) iodide In water; acetone at 20℃;
55%
2-chloro-9-cyclopentyl-5-methyl-5,7,8,9-tetrahydro-6H-pyrimido[4,5-b][1,4]diazepin-6-one
946825-98-5

2-chloro-9-cyclopentyl-5-methyl-5,7,8,9-tetrahydro-6H-pyrimido[4,5-b][1,4]diazepin-6-one

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

6-cyclopentyl-9-[[3-(2-hydroxyethyl)phenyl]amino]-2-methyl-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-3-one

6-cyclopentyl-9-[[3-(2-hydroxyethyl)phenyl]amino]-2-methyl-2,6,8,10-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-3-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In Methyl isobutyl carbinol at 140℃; for 2h;50%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

para-chlorobenzoic acid
74-11-3

para-chlorobenzoic acid

C15H14ClNO2

C15H14ClNO2

Conditions
ConditionsYield
Stage #1: para-chlorobenzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine In dichloromethane for 0.25h;
Stage #2: 2-(3-aminophenyl)ethan-1-ol In dichloromethane at 25℃; for 12h;
49.6%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Dibenzyl phosphite
17176-77-1

Dibenzyl phosphite

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

dibenzyl (3-(N-Boc-amino)phenethyl)phosphonate

dibenzyl (3-(N-Boc-amino)phenethyl)phosphonate

Conditions
ConditionsYield
Stage #1: di-tert-butyl dicarbonate; 2-(3-aminophenyl)ethan-1-ol In 1,4-dioxane at 20℃;
Stage #2: With triethylamine In dichloromethane for 0.166667h; Cooling with ice;
Stage #3: Dibenzyl phosphite Further stages;
43%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

acetic anhydride
108-24-7

acetic anhydride

1′-(3-acetamidophenyl)ethan-2′-ol

1′-(3-acetamidophenyl)ethan-2′-ol

Conditions
ConditionsYield
In dichloromethane at 20℃; for 24h; Inert atmosphere;42%
2-chloroethyl isothiocyanate
1943-83-5

2-chloroethyl isothiocyanate

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

1-(2-chloro-ethyl)-3-[3-(2-hydroxy-ethyl)-phenyl]-urea

1-(2-chloro-ethyl)-3-[3-(2-hydroxy-ethyl)-phenyl]-urea

Conditions
ConditionsYield
In dichloromethane at 20℃; for 20h;41%
2,3-Dichloro-1,4-naphthoquinone
117-80-6

2,3-Dichloro-1,4-naphthoquinone

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

2-chloro-3-((3-(2-hydroxyethyl)phenyl)amino)naphthalene-1,4-dione

2-chloro-3-((3-(2-hydroxyethyl)phenyl)amino)naphthalene-1,4-dione

Conditions
ConditionsYield
In ethanol at 20℃;31%
ethyl 4-oxocyclohexane-1-carboxylate
17159-79-4

ethyl 4-oxocyclohexane-1-carboxylate

2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

methyl trans-4-{[3-(2-hydroxyethyl)phenyl]amino}cyclohexanecarboxylate

methyl trans-4-{[3-(2-hydroxyethyl)phenyl]amino}cyclohexanecarboxylate

Conditions
ConditionsYield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃; for 4h;19%
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

N,N-dimethyl-formamide dimethyl acetal
4637-24-5

N,N-dimethyl-formamide dimethyl acetal

N'-[3-(2-Hydroxy-ethyl)-phenyl]-N,N-dimethyl-formamidine

N'-[3-(2-Hydroxy-ethyl)-phenyl]-N,N-dimethyl-formamidine

Conditions
ConditionsYield
In N,N-dimethyl-formamide for 20h; Ambient temperature;
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid 2-(3-isothiocyanato-phenyl)-ethyl ester

(E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid 2-(3-isothiocyanato-phenyl)-ethyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 77 percent / tetrahydrofuran / 0.5 h / 20 °C
2.1: pyridine / toluene / 20 °C
2.2: 40 percent / Et3N; HSiCl3 / benzene / 1 h / 20 °C
3.1: 93 percent / HF*pyridine / tetrahydrofuran / 4 h / 20 °C
View Scheme
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

2-(3-isothiocyanatophenyl)ethyl O,O-(3,4-bis(1,1,2,2-tetramethyl-1-silapropyl))caffeic acid ester

2-(3-isothiocyanatophenyl)ethyl O,O-(3,4-bis(1,1,2,2-tetramethyl-1-silapropyl))caffeic acid ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 77 percent / tetrahydrofuran / 0.5 h / 20 °C
2.1: pyridine / toluene / 20 °C
2.2: 40 percent / Et3N; HSiCl3 / benzene / 1 h / 20 °C
View Scheme
2-(3-aminophenyl)ethan-1-ol
52273-77-5

2-(3-aminophenyl)ethan-1-ol

[3-(2-Bromo-ethyl)-phenyl]-carbamic acid tert-butyl ester
1026069-85-1

[3-(2-Bromo-ethyl)-phenyl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
2: CBr4, PPh3
View Scheme

52273-77-5Relevant articles and documents

Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes

Fu, Lihua,Li, Dingzhong,Lu, Hao,Qiu, Renhua,Sun, Tulai,Xing, Chen,Yang, Tianbao

, (2022/01/11)

The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).

Synthesis of Functionalized Indolines and Dihydrobenzofurans by Iron and Copper Catalyzed Aryl C-N and C-O Bond Formation

Henry, Martyn C.,Senn, Hans Martin,Sutherland, Andrew

, p. 346 - 364 (2019/01/08)

A simple and effective one-pot, two-step intramolecular aryl C-N and C-O bond forming process for the preparation of a wide range of benzo-fused heterocyclic scaffolds using iron and copper catalysis is described. Activated aryl rings were subjected to a highly regioselective, iron(III) triflimide-catalyzed iodination, followed by a copper(I)-catalyzed intramolecular N-or O-arylation step leading to indolines, dihydrobenzofurans, and six-membered analogues. The general applicability and functional group tolerance of this method were exemplified by the total synthesis of the neolignan natural product, (+)-obtusafuran. DFT calculations using Fukui functions were also performed, providing a molecular orbital rationale for the highly regioselective arene iodination process.

QUINOLONE DERIVATIVES AS FIBROBLAST GROWTH FACTOR RECEPTOR INHIBITORS

-

Page/Page column 78, (2016/12/16)

Compounds of formula (I) that are Fibroblast Growth Factor Inhibitors (FGFR) and are therefore useful for the treatment of diseases treatable by inhibition of FGFR are disclosed. Also disclosed are pharmaceutical compositions containing such compounds and processes for preparing such compounds.

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