518060-42-9

Basic information

• Product Name: (R)-3-(1-AMINOETHYL)PHENOL
• Synonyms: 3[(1R)-1-AMINOETHYL] PHENOL;(R)-3-(1-AMINOETHYL)PHENOL;1-(R)-(3-METHOXYPHENOL)ETHYLAMINE;Phenol, 3-[(1R)-1-aminoethyl]- (9CI);Phenol, 3-[(1R)-1-aminoethyl]-;R-3-Hydroxy-α-methylbenzylamine
• CAS NO: 518060-42-9
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• Product Categories: ALCOHOL;API intermediates
• Mol File: 518060-42-9.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 266.3±15.0 °C(Predicted)
• Appearance: /
• Density: 1.096±0.06 g/cm3(Predicted)
• PKA: 9.86±0.10(Predicted)
• CAS DataBase Reference: (R)-3-(1-AMINOETHYL)PHENOL(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(1-AMINOETHYL)PHENOL(518060-42-9)
• EPA Substance Registry System: (R)-3-(1-AMINOETHYL)PHENOL(518060-42-9)

Safety Data

• Hazardous Substances Data: 518060-42-9(Hazardous Substances Data)

Usage

General Description

(R)-3-(1-Aminoethyl)phenol is a chemical compound with the molecular formula C8H11NO. It is a chiral compound, with a single chiral center, and exists as two enantiomers: (R)-3-(1-Aminoethyl)phenol and (S)-3-(1-Aminoethyl)phenol. The compound is a catecholamine derivative and can be used as a precursor in the synthesis of various pharmaceuticals and organic compounds. It has potential applications in the pharmaceutical and chemical industries due to its role as a building block for various synthetic processes. Additionally, it has been studied for its potential pharmacological properties and is of interest in the development of new drugs and therapeutic agents.

Synthetic route

3-((R)-1-((R)-1-phenylethylamino)ethyl)phenol (1372628-56-2) → (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In acetic acid at 20℃; under 3102.97 Torr; for 48h; Inert atmosphere; optical yield given as %ee; enantioselective reaction;	89.7%

(R)-1-(3-tert-butoxyphenyl)ethylamine → (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
Stage #1: (R)-1-(3-tert-butoxyphenyl)ethylamine With sulfuric acid; water at 85℃; for 3h; pH=1; Stage #2: With sodium hydroxide; water pH=9.1;	73%

(R)-[1-(3-methoxyphenyl)ethyl]carbamic acid tert-butyl ester (871728-33-5) → (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
With boron tribromide In dichloromethane at -78 - 20℃;

(R)-1-(3-methoxyphenyl)ethylamine (88196-70-7) → (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 5 h / 20 °C 2: BBr3 / CH2Cl2 / -78 - 20 °C View Scheme
Stage #1: (R)-1-(3-methoxyphenyl)ethylamine With boron tribromide In dichloromethane at -78℃; Stage #2: With methanol In dichloromethane at 20℃;
With boron tribromide In dichloromethane for 48h; Inert atmosphere; Cooling with ice;

3-Hydroxyacetophenone (121-71-1) → 3-hydroxy-(S)-α-phenethylamine (63720-38-7, 123982-81-0) + (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
With glucose dehydrogenase; D-Glucose; L-alanin; Arthrobacter sp. CNB05-01 ω-transaminase; nicotiamide adenine dinucleotide; lactate dehydrogenase at 30℃; for 24h; pH=7; aq. phosphate buffer; Enzymatic reaction;

C16H17NO → (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium tetrahydroborate / ethanol; ethyl acetate / 3 h / 0 °C / Inert atmosphere 2: palladium 10% on activated carbon; hydrogen / acetic acid / 48 h / 20 °C / 3102.97 Torr / Inert atmosphere View Scheme

3-Hydroxyacetophenone (121-71-1) → (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: titanium(IV) isopropylate / ethyl acetate / 3 h / Inert atmosphere 2: sodium tetrahydroborate / ethanol; ethyl acetate / 3 h / 0 °C / Inert atmosphere 3: palladium 10% on activated carbon; hydrogen / acetic acid / 48 h / 20 °C / 3102.97 Torr / Inert atmosphere View Scheme

C8H11NO*0.5C4H6O6 → 3-hydroxy-(S)-α-phenethylamine (63720-38-7, 123982-81-0) + (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
With sodium hydroxide In water Overall yield = 1.41 g;

C8H11NO*0.5C4H6O6 → 3-hydroxy-(S)-α-phenethylamine (63720-38-7, 123982-81-0) + (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9)

Conditions	Yield
With sodium hydroxide In water

di-tert-butyl dicarbonate (24424-99-5) + (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-[1-(3-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester (266369-69-1)

Conditions	Yield
With triethylamine In methanol at 0℃; for 6h; Inert atmosphere;	81.7%
With triethylamine In dichloromethane at 20℃; for 0.5h;	66%
With triethylamine In dichloromethane at 20℃; for 0.5h;
With triethylamine In dichloromethane for 1h;

2-(6-{5-chloro-2-[(oxan-4-yl)amino]pyrimidin-4-yl}-1-oxo-2,3-dihydro-1H-isoindol-2-yl)acetic acid + (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → 2-(6-{5-chloro-2-[(oxan-4-yl)amino]pyrimidin-4-yl}-1-oxo-2,3-dihydro-1H-isoindol-2-yl)-N-[(1R)-1-(3-hydroxyphenyl)ethyl]acetamide

Conditions	Yield
With triethylamine; HATU In N,N-dimethyl-formamide for 1h;	80%

6-chloro-1-cyclopentyl-1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-one + (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-1-cyclopentyl-6-((1-(3-hydroxyphenyl)ethyl)amino)-1Hpyrazolo[3,4-d]pyrimidin-4(5H)-one

Conditions	Yield
With triethylamine In isopropyl alcohol at 80℃; for 1h;	68%

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-[1-(3-morpholin-4-yl-phenyl)ethyl]-carbamic acid tert-butyl ester

Conditions	Yield
Multi-step reaction with 3 steps 1: Et3N / CH2Cl2 / 0.5 h / 20 °C 2: Et3N / CH2Cl2 / 0.5 h / 20 °C 3: tris(dibenzylideneacetone)dipalladium; 2-(di-tert-butylphosphino)-biphenyl; K3PO4 / 12 h / 80 °C View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-trifluoromethanesulfonic acid 3-(1-tert-butoxycarbonylamino-ethyl)-phenyl ester

Conditions	Yield
Multi-step reaction with 2 steps 1: Et3N / CH2Cl2 / 0.5 h / 20 °C 2: Et3N / CH2Cl2 / 0.5 h / 20 °C View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (E)-N-[(R)-1-(3-Morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide

Conditions	Yield
Multi-step reaction with 5 steps 1: Et3N / CH2Cl2 / 0.5 h / 20 °C 2: Et3N / CH2Cl2 / 0.5 h / 20 °C 3: tris(dibenzylideneacetone)dipalladium; 2-(di-tert-butylphosphino)-biphenyl; K3PO4 / 12 h / 80 °C 4: HCl / methanol; diethyl ether / 12 h / 20 °C 5: 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; DMAP; Et3N / CH2Cl2 / 12 h / 20 °C View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-1-(3-morpholin-4-yl-phenyl)ethylamine dihydrochloride

Conditions	Yield
Multi-step reaction with 4 steps 1: Et3N / CH2Cl2 / 0.5 h / 20 °C 2: Et3N / CH2Cl2 / 0.5 h / 20 °C 3: tris(dibenzylideneacetone)dipalladium; 2-(di-tert-butylphosphino)-biphenyl; K3PO4 / 12 h / 80 °C 4: HCl / methanol; diethyl ether / 12 h / 20 °C View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → 3-(2-chlorophenyl)-N-[(R)-1-(3-methoxyphenyl)ethyl]-2-propenamide (1006592-90-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / methanol / 6 h / 0 °C / Inert atmosphere 2: potassium carbonate / acetone / 0 °C / Inert atmosphere; Reflux 3: hydrogenchloride; water / methanol / 12 h / 20 °C / Inert atmosphere 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-1-(3-methoxyphenyl)ethanamine hydrochloride salt (1167414-89-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / methanol / 6 h / 0 °C / Inert atmosphere 2: potassium carbonate / acetone / 0 °C / Inert atmosphere; Reflux 3: hydrogenchloride; water / methanol / 12 h / 20 °C / Inert atmosphere View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → tecalcet

Conditions

Yield

Multi-step reaction with 6 steps 1: triethylamine / methanol / 6 h / 0 °C / Inert atmosphere 2: potassium carbonate / acetone / 0 °C / Inert atmosphere; Reflux 3: hydrogenchloride; water / methanol / 12 h / 20 °C / Inert atmosphere 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 5: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 2585.81 Torr / Inert atmosphere 6: diisobutylaluminium hydride / hexane; dichloromethane / 0 - 20 °C / Inert atmosphere View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-3-(2-chlorophenyl)-N-(1-(3'-methoxyphenyl)ethyl)propanamide (177172-48-4)

Conditions

Yield

Multi-step reaction with 5 steps 1: triethylamine / methanol / 6 h / 0 °C / Inert atmosphere 2: potassium carbonate / acetone / 0 °C / Inert atmosphere; Reflux 3: hydrogenchloride; water / methanol / 12 h / 20 °C / Inert atmosphere 4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere 5: palladium 10% on activated carbon; hydrogen / methanol / 3 h / 20 °C / 2585.81 Torr / Inert atmosphere View Scheme

C13H8F3IN2O (1297594-71-8) + (R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → C21H18F2IN3O2

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 50℃; regioselective reaction;

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → tert-butyl (R)-(1-(3-(methoxy-d3)phenyl)ethyl)carbamate

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 1 h 2: potassium carbonate / N,N-dimethyl-formamide / 22 h View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → (R)-1-(3-(methoxy-d3)phenyl)ethan-1-amine hydrochloride

Conditions	Yield
Multi-step reaction with 3 steps 1: triethylamine / dichloromethane / 1 h 2: potassium carbonate / N,N-dimethyl-formamide / 22 h 3: hydrogenchloride / 1,4-dioxane; water / 20 h View Scheme

(R)-1-(3-hydroxyphenyl)ethylamine (518060-42-9) → 4-nitrophenyl (R)-(1-(3-(methoxy-d3)phenyl)ethyl)carbamate

Conditions	Yield
Multi-step reaction with 4 steps 1: triethylamine / dichloromethane / 1 h 2: potassium carbonate / N,N-dimethyl-formamide / 22 h 3: hydrogenchloride / 1,4-dioxane; water / 20 h 4: pyridine / dichloromethane / 3 h / Inert atmosphere View Scheme

Upstream product

• 871728-33-5 (R)-[1-(3-methoxyphenyl)ethyl]carbamic acid tert-butyl ester 
• 917911-64-9 (R)-1-(3-tert-butoxyphenyl)ethylamine 
• 121-71-1 3-Hydroxyacetophenone 
• 88196-70-7 (R)-1-(3-methoxyphenyl)ethylamine 
• 1372628-56-2 3-((R)-1-((R)-1-phenylethylamino)ethyl)phenol 

Downstream Products

• 1006592-90-0 3-(2-chlorophenyl)-N-[(R)-1-(3-methoxyphenyl)ethyl]-2-propenamide 
• 1167414-89-2 (R)-1-(3-methoxyphenyl)ethanamine hydrochloride salt 
• 148717-49-1 tecalcet 
• 177172-48-4 (R)-3-(2-chlorophenyl)-N-(1-(3'-methoxyphenyl)ethyl)propanamide 
• 266369-69-1 (R)-[1-(3-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester 

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