52273-77-5

Basic information

• Product Name: 2-(3-Aminophenyl)ethanol
• Synonyms: 2-(3-Aminophenyl)ethanol;3-Aminophenethyl alcohol;3-(2-Hydroxyethyl)aniline;Benzeneethanol, 3-aMino-
• CAS NO: 52273-77-5
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 1308068-626-2
• Mol File: 52273-77-5.mol
• Article Data: 23

Chemical Properties

• Melting Point: 51-53 ºC
• Boiling Point: 293 ºC
• Flash Point: 131 ºC
• Appearance: /
• Density: 1.124
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.597
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 14.91±0.10(Predicted)
• CAS DataBase Reference: 2-(3-Aminophenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3-Aminophenyl)ethanol(52273-77-5)
• EPA Substance Registry System: 2-(3-Aminophenyl)ethanol(52273-77-5)

Safety Data

• Hazardous Substances Data: 52273-77-5(Hazardous Substances Data)

Usage

Uses

2-(3-Aminophenyl)ethanol is a useful compound for the synthesis of indolines and dihydrobenzofurans via iron and copper-catalyzed iodination and cyclization.

InChI:InChI=1/C8H11NO/c9-8-3-1-2-7(6-8)4-5-10/h1-3,6,10H,4-5,9H2

Synthetic route

2-(3-nitrophenyl)ethanol (52022-77-2) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

Conditions	Yield
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%

Pd-C (125620-28-2) + 2-(3-nitrophenyl)ethanol (52022-77-2) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

Conditions	Yield
In ethanol; water	100%

(3-amino-phenyl)-acetic acid ethyl ester (52273-79-7) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

Conditions	Yield
With lithium aluminium tetrahydride In 1,4-dioxane Ambient temperature;	40%

3-amino phenylacetic acid (14338-36-4) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

Conditions	Yield
With lithium aluminium tetrahydride

2-(4-amino-3-nitrophenyl)ethanol (15896-61-4) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

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

Conditions	Yield
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) + pyrographite (7440-44-0) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

Conditions	Yield
In ethanol

(3-nitrophenyl)acetonitrile (621-50-1) → 2-(3-aminophenyl)ethan-1-ol (52273-77-5)

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

Conditions	Yield
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) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → chloroethyl carbamate

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water	100%

5-chloro-1H-Indole-2-carboxylic acid (10517-21-2) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → C17H15ClN2O2 (1036750-34-1)

Conditions	Yield
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-(3-aminophenyl)ethan-1-ol (52273-77-5) → 2-{3-[(5-chloro-4-{[2-(3-methoxyphenyl)ethyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol (1236130-79-2)

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane at 100℃; for 16h;	96%

2-(3-aminophenyl)ethan-1-ol (52273-77-5) + 4-chloro-6,7-bis(2-methoxyethoxy)quinazoline (183322-18-1) → 2-(3-((6,7-bis(2-methoxyethoxy)quinazolin-4-yl)amino)phenyl)ethan-1-ol

Conditions	Yield
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-(3-aminophenyl)ethan-1-ol (52273-77-5) → 2-{3-[(5-chloro-4-{[3-(3-methoxyphenyl)propyl]amino}pyrimidin-2-yl)amino]phenyl}ethanol (1236130-89-4)

Conditions	Yield
With toluene-4-sulfonic acid In 1,4-dioxane at 100℃; for 16h;	92%

di-tert-butyl dicarbonate (24424-99-5) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → tert-butyl N-[3-(2-hydroxyethyl)phenyl]carbamate (180002-10-2)

Conditions	Yield
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) + phenylcarbonochloridothioate (1005-56-7) → 2-(3-((phenoxythioxomethyl)amino)phenyl)ethan-1-ol (366492-72-0)

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h;	77%

2-(3-aminophenyl)ethan-1-ol (52273-77-5) + ortho-nitrofluorobenzene (1493-27-2) → 2-(3-((2-nitrophenyl)amino)phenyl)ethanol (1429642-71-6)

Conditions	Yield
With triethylamine at 110℃; for 15h; Sealed tube;	77%

2,5-dichloro-N-(3-methoxybenzyl)pyrimidin-4-amine (1236130-57-6) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → 2-[3-({5-Chloro-4-[(3-methoxybenzyl)amino]pyrimidin-2-yl}amino)phenyl]ethanol (1236130-60-1)

Conditions	Yield
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-(3-aminophenyl)ethan-1-ol (52273-77-5) → N-[3-(2-hydroxyethyl)phenyl]-2,4-dimethyl-1,3-thiazole-5-carboxamide (844904-20-7)

Conditions	Yield
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-iodophenyl)ethan-1-ol (127201-31-4)

Conditions	Yield
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) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → 9-[3'-(β-hydroxyethyl)anilino]-3-methoxyacridine (135785-71-6)

Conditions	Yield
With methanesulfonic acid In methanol	65%

2-(3-aminophenyl)ethan-1-ol (52273-77-5) → BrH*C8H10BrN (914605-41-7)

Conditions	Yield
With hydrogen bromide In water at 90℃; for 18h;	61%

2-(3-aminophenyl)ethan-1-ol (52273-77-5) + acrylic acid methyl ester (292638-85-8) → methyl 2-chloro-3-[3-(2-hydroxyethyl)phenyl]propanoate (817642-95-8)

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

2-(3-aminophenyl)ethan-1-ol (52273-77-5) + para-chlorobenzoic acid (74-11-3) → C15H14ClNO2

Conditions	Yield
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) + Dibenzyl phosphite (17176-77-1) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → dibenzyl (3-(N-Boc-amino)phenethyl)phosphonate

Conditions	Yield
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) + acetic anhydride (108-24-7) → 1′-(3-acetamidophenyl)ethan-2′-ol

Conditions	Yield
In dichloromethane at 20℃; for 24h; Inert atmosphere;	42%

2-chloroethyl isothiocyanate (1943-83-5) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → 1-(2-chloro-ethyl)-3-[3-(2-hydroxy-ethyl)-phenyl]-urea

Conditions	Yield
In dichloromethane at 20℃; for 20h;	41%

2,3-Dichloro-1,4-naphthoquinone (117-80-6) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → 2-chloro-3-((3-(2-hydroxyethyl)phenyl)amino)naphthalene-1,4-dione

Conditions	Yield
In ethanol at 20℃;	31%

ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) + 2-(3-aminophenyl)ethan-1-ol (52273-77-5) → methyl trans-4-{[3-(2-hydroxyethyl)phenyl]amino}cyclohexanecarboxylate

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃; for 4h;	19%

2-(3-aminophenyl)ethan-1-ol (52273-77-5) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → N'-[3-(2-Hydroxy-ethyl)-phenyl]-N,N-dimethyl-formamidine

Conditions	Yield
In N,N-dimethyl-formamide for 20h; Ambient temperature;

2-(3-aminophenyl)ethan-1-ol (52273-77-5) → (E)-3-(3,4-Dihydroxy-phenyl)-acrylic acid 2-(3-isothiocyanato-phenyl)-ethyl ester

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

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

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

Upstream product

• 52022-77-2 2-(3-nitrophenyl)ethanol 
• 1877-73-2 3-nitro-benzeneacetic acid 
• 621-50-1 (3-nitrophenyl)acetonitrile 
• 7440-44-0 pyrographite 
• 125620-28-2 Pd-C 
• 92959-73-4 4-acetamido-3-nitrophenethyl acetate 
• 15896-61-4 2-(4-amino-3-nitrophenyl)ethanol 
• 52273-79-7 (3-amino-phenyl)-acetic acid ethyl ester 
• 14338-36-4 3-amino phenylacetic acid 

Downstream Products

• 366492-72-0 2-(3-((phenoxythioxomethyl)amino)phenyl)ethan-1-ol 
• 180002-10-2 tert-butyl N-[3-(2-hydroxyethyl)phenyl]carbamate 
• 127201-31-4 2-(3-iodophenyl)ethan-1-ol 
• 183321-74-6 erlotinib 
• 1104503-41-4 C₁₅H₁₇N₃O₂ 
• 123306-34-3 1-(3-Acetylaminophenyl)ethylacetat 

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