7568-93-6

Basic information

• Product Name: 2-AMINO-1-PHENYLETHANOL
• Synonyms: DL-PhenylethanolaMine;beta-Hydroxyphenethylamine, 2-Amino-1-phenylethan-1-ol;β-Hydroxyphenylethyl;alpha-(Aminomethyl)benzyl Alcohol Phenylethanolamine;231-469-1;Benzenemethanol, a-(aminomethyl)-;alpha-(Aminomethyl)benzylalcohol,tech;(±)-1-Phenylethanolamine
• CAS NO: 7568-93-6
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 231-469-1
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 7568-93-6.mol
• Article Data: 56

Chemical Properties

• Melting Point: 56-58 °C(lit.)
• Boiling Point: 160 °C17 mm Hg(lit.)
• Flash Point: 125.3oC
• Appearance: Clear yellow/Viscous Liquid
• Density: 1.0630 (rough estimate)
• Vapor Pressure: 0.00148mmHg at 25°C
• Refractive Index: 1.558-1.56
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 12.04±0.35(Predicted)
• Water Solubility: 43.79g/L(20 oC)
• Stability: Stable. Incompatible with oxidizing agents, acids, acid chlorides, acid anhydrides.
• Merck: 14,7287
• BRN: 971222
• CAS DataBase Reference: 2-AMINO-1-PHENYLETHANOL(CAS DataBase Reference)
• NIST Chemistry Reference: 2-AMINO-1-PHENYLETHANOL(7568-93-6)
• EPA Substance Registry System: 2-AMINO-1-PHENYLETHANOL(7568-93-6)

Safety Data

• Hazard Codes: Xi,C
• Statements: 36/37/38
• Safety Statements: 26-36
• RIDADR: 3259
• WGK Germany: 3
• RTECS: DN5500000
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 7568-93-6(Hazardous Substances Data)

Usage

Chemical Properties

white solid

Uses

2-Amino-1-phenylethanol is an intermediate in the manufacturing of pressor amines. The sulfate salt is used as topical vasoconstrictor.

Definition

ChEBI: The simplest member of the class of phenylethanolamines that is 2-aminoethanol bearing a phenyl substituent at the 1-position. The parent of the phenylethanolamine class.

InChI:InChI=1/C8H11NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H,6,9H2/p+1/t8-/m0/s1

Synthetic route

2-azido-1-phenylethan-1-ol (124718-87-2) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With Zn(BH4)2(Ph3P)2 In tetrahydrofuran Reduction; Heating;	100%
With (1,4-diazabicyclo{2.2.2}-octane)zinc(II) tetrahydoborate In tetrahydrofuran for 0.34h; Heating;	95%
With sodium tetrahydroborate; zirconium(IV) chloride In tetrahydrofuran at 0 - 35℃; for 0.333333h; Reduction;	90%

2-diphenylmethylenamino-1-phenylethanol (51411-44-0) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With hydrogenchloride	100%

5-phenyloxazolidin-2-one (7693-77-8, 54705-41-8, 60426-44-0) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With N-(2-Aminoethyl)aminomethyl polystyrene In tetrahydrofuran at 60℃;	99%

2-(2-hydroxy-2-phenyl-ethyl)-isoindole-1,3-dione (35645-98-8) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With hydrazine hydrate In water at 60℃; for 3h;	97%
With sodium hydroxide
With hydrazine hydrate In ethanol for 4h; Heating; Yield given;

(+/-)-1-[1-(tert-butylperoxy)-2-nitroethyl]benzene (37733-99-6) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With palladium on activated charcoal; hydrogen In methanol at 20℃; Inert atmosphere;	90%
With palladium on activated charcoal; hydrogen In methanol at 20℃; under 760.051 Torr; for 5h;

N-<(trimethylsilyl)methyl>benzaldimine (57402-97-8) + benzaldehyde (100-52-7) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran; N,N-dimethyl-formamide for 48h; Ambient temperature;	88%

2-phenylaziridine (1499-00-9) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With (phthalocyaninato)iron(II); O-pivaloylhydroxylamine trifluoromethanesulfonate salt In water; acetonitrile at 25℃; for 16h; Inert atmosphere; regioselective reaction;	88%
With water In dimethyl sulfoxide at 20℃; for 6h; pH=7.4;
Multi-step reaction with 2 steps 1: tetrahydrofuran / 0.5 h / 120 °C / Microwave irradiation; Sealed tube 2: hydrogenchloride; water / 10 h / 100 °C / Sealed tube View Scheme

2-aminoacetophenone hydrochloride (5468-37-1) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With sodium tetrahydroborate In methanol at 0℃; for 0.5h;	85%

styrene oxide (96-09-3) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
Stage #1: styrene oxide With sodium hexamethyldisilazane In tetrahydrofuran at 0 - 25℃; for 20h; Stage #2: With water In tetrahydrofuran at 25℃; for 5h; regioselective reaction;	81%
With ammonia In methanol; water at 4℃; for 360h;	66.5%
With ammonia In methanol

styrene (292638-84-7) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With (phthalocyaninato)iron(II); O-pivaloylhydroxylamine trifluoromethanesulfonate salt In water; acetonitrile at 25℃; for 16h; Reagent/catalyst; Temperature; Inert atmosphere; regioselective reaction;	74%
With lithium aluminium tetrahydride; sodium azide; oxygen; rhodamine B 1.) MeOH/H2O, irradiation, 30 deg C; 2.) Et2O2, cooling; Multistep reaction;
Multi-step reaction with 2 steps 1: diluted bromo potassium bromide / 90 °C 2: ammonia View Scheme

C25H21N3O3Si (88626-81-7) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With lithium aluminium tetrahydride	70%

(RS)-mandelonitrile (532-28-5, 613-88-7) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran a) 0 deg C, 6 h, b) RT, overnight, c) reflux, 4 h;	64%
With sodium amalgam
With lithium aluminium tetrahydride In diethyl ether Heating;

(E)-4,4-dimethyl-2-(5-phenyloxazolidin-2-ylidene)cyclopentan-1-one → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
Stage #1: (E)-4,4-dimethyl-2-(5-phenyloxazolidin-2-ylidene)cyclopentan-1-one With hydrogenchloride; water at 100℃; for 10h; Sealed tube; Stage #2: With sodium hydroxide In water Mechanism; Temperature;	56%

phenyl(trimethylsiloxy)acetonitrile (25438-37-3) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With B2H6-THF	55%
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃;

N-(2-hydroxy-2-phenylethyl)acetamide (3306-05-6) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With hydrogenchloride at 80℃; for 5h;	48%

trimethylsilyl cyanide (7677-24-9) + benzaldehyde (100-52-7) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
Stage #1: trimethylsilyl cyanide; benzaldehyde With potassium cyanide; 18-crown-6 ether In dichloromethane at 25℃; for 14h; Stage #2: With lithium aluminium tetrahydride In diethyl ether at 25℃; for 5h;	37%

N-(2-hydroxy-2-phenylethyl)-2,2,2-trifluoroacetylamide (91994-60-4) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With water; potassium carbonate In methanol for 2h; Reflux;	29%
With potassium carbonate In methanol; water for 2h; Heating;	25%

2,2,2-trifluoro-N-(2-oxo-2-phenylethyl)acetamide (91994-49-9) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With sodium tetrahydroborate In ethanol for 12h;	25%
Multi-step reaction with 2 steps 1: 86 percent / H2 / Pd-C / ethanol / 12 h / 2275.5 Torr 2: 25 percent / K2CO3 / methanol; H2O / 2 h / Heating View Scheme

benzoyl cyanide (613-90-1) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With lithium aluminium tetrahydride
With palladium; acetic acid Hydrogenation;

styrene oxide (96-09-3) → 2,6-diphenyl-morpholine + 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With ammonium hydroxide isomer(ic) II;

styrene oxide (96-09-3) → Phenylglycinol (20989-17-7, 56613-80-0, 71006-16-1, 7568-92-5, 188586-38-1) + 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With ethanol; ammonia

N-hydroxy-2-oxo-2-phenylethanimidoyl chloride (4937-87-5) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With palladium on activated charcoal; platinum on activated charcoal; ethanol under 7355.08 - 14710.2 Torr; Hydrogenation;
With lithium aluminium tetrahydride

2-diazo-acetophenone (3282-32-4) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With lithium aluminium tetrahydride
With lithium aluminium tetrahydride In diethyl ether

N-(2-hydroxy-2-phenylethyl)-2,5-pyrrolidinedione (68239-22-5) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With sodium hydroxide
With hydrogenchloride

oxo-phenyl-acetaldehyde oxime (532-54-7) → 2-Aminoacetophenone (613-89-8) + 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With hydrogenchloride; sodium amalgam; ethanol

oxo-phenyl-acetaldehyde oxime (532-54-7) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With hydrogenchloride; sodium amalgam; ethanol
With lithium aluminium tetrahydride In diethyl ether

2-Bromo-1-phenylethanol (2425-28-7) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With ammonia
Multi-step reaction with 2 steps 1: NH3*H2O 2: NH3*H2O / ethanol / 20 °C View Scheme

2-nitro-1-phenylethan-1-ol (141377-54-0, 145920-96-3, 149495-00-1, 15990-45-1) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With sodium amalgam; acetic acid
With aluminium amalgam; acetic acid
With sodium amalgam; ethanol

(RS)-mandelamide (4410-31-5, 24008-62-6, 24008-63-7, 4358-86-5) → 2-Amino-1-phenylethanol (7568-93-6)

Conditions	Yield
With lithium aluminium tetrahydride

di-tert-butyl dicarbonate (24424-99-5) + 2-Amino-1-phenylethanol (7568-93-6) → tert-butyl N-(2-hydroxy-2-phenylethyl)carbamate (67341-07-5)

Conditions	Yield
With triethylamine In dichloromethane at 20℃;	100%
In tetrahydrofuran at 0 - 20℃; for 0.5h;	100%
In tetrahydrofuran at 0 - 20℃; for 0.5h;	100%

2-bromobenzoic acid chloride (7154-66-7) + 2-Amino-1-phenylethanol (7568-93-6) → 2-bromo-N-(2-hydroxy-2-phenylethyl)-benzamide (380427-62-3)

Conditions	Yield
With triethylamine In dichloromethane for 2h;	100%

(R)-6-oxo-1,2-dithio-5-azacyclododecane-4-carboxylic acid (945031-70-9) + 2-Amino-1-phenylethanol (7568-93-6) → (R)-N-(2-hydroxy-2-phenylethyl)-6-oxo-1,2-dithia-5-azacyclododecane-4-carboxamide

Conditions	Yield
Stage #1: (R)-6-oxo-1,2-dithio-5-azacyclododecane-4-carboxylic acid With N-ethyl-N,N-diisopropylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 0.5h; Stage #2: 2-Amino-1-phenylethanol In tetrahydrofuran at 20℃; for 18h; Further stages.;	100%

Isopropenyl acetate (108-22-5) + 2-Amino-1-phenylethanol (7568-93-6) → N-(2-hydroxy-2-phenylethyl)acetamide (3306-05-6)

Conditions	Yield
In neat (no solvent) at 20℃; for 24h; Green chemistry;	100%
at 60℃; for 3h;
at 20℃; for 24h;	0.179 g

methyl trifluoromethanesulfonate (333-27-7) + 2-Amino-1-phenylethanol (7568-93-6) → 1-(2-hydroxy-2-phenylethyl)-3-methyl-1H-imidazol-3-ium trifluoromethanesulfonate (1448544-00-0)

Conditions	Yield
In acetonitrile at 0 - 20℃; for 0.166667h; Inert atmosphere;	100%

acetic anhydride (108-24-7) + 2-Amino-1-phenylethanol (7568-93-6) → 2-acetamido-1-phenylethyl acetate (55044-72-9)

Conditions	Yield
With dmap; triethylamine In dichloromethane	99%
With dmap; triethylamine In dichloromethane for 4h; Ambient temperature;	75%
With pyridine

4-nitrobenzaldehdye (555-16-8) + 2-Amino-1-phenylethanol (7568-93-6) → 2-[(4-nitrobenzylidene)amino]-1-phenylethan-1-ol (93733-50-7)

Conditions	Yield
In methanol at 20℃; for 0.0833333h;	99%
With magnesium sulfate In dichloromethane for 2h; Ambient temperature;

benzaldehyde (100-52-7) + 2-Amino-1-phenylethanol (7568-93-6) → 2-(benzylideneamino)-1-phenylethan-1-ol (25558-12-7)

Conditions	Yield
In methanol at 20℃; for 0.0833333h;	99%
With magnesium sulfate In dichloromethane for 2h; Ambient temperature;
With magnesium sulfate In dichloromethane Ambient temperature;

4-fluorophenyl isothiocyanate (1544-68-9) + 2-Amino-1-phenylethanol (7568-93-6) → N-(4-fluorophenyl)-N'-(2-hydroxy-2-phenylethyl)thiourea (121541-06-8)

Conditions	Yield
In toluene Ambient temperature;	99%

ethyl acetoacetate (141-97-9) + 2-Amino-1-phenylethanol (7568-93-6) → (E)-3-(2-Hydroxy-2-phenyl-ethylamino)-but-2-enoic acid ethyl ester

Conditions	Yield
With 4 A molecular sieve In tetrahydrofuran for 168h; Ambient temperature;	99%
With 4 A molecular sieve In tetrahydrofuran at 20℃; for 168h;	99%

5-chloro-1H-indole-3-carboxaldehyde (827-01-0) + 2-Amino-1-phenylethanol (7568-93-6) → C17H15ClN2O

Conditions	Yield
In toluene for 16h; Heating / reflux;	99%

acetic anhydride (108-24-7) + benzyl chloroformate (501-53-1) + 2-Amino-1-phenylethanol (7568-93-6) → (RS)-2-(((benzyloxy)carbonyl)amino)-1-phenylethyl acetate

Conditions	Yield
Stage #1: benzyl chloroformate; 2-Amino-1-phenylethanol With sodium hydroxide In dichloromethane; water; toluene at 0 - 20℃; for 16h; Stage #2: acetic anhydride With dmap; triethylamine In dichloromethane	99%

4-chlorobenzaldehyde (104-88-1) + 2-Amino-1-phenylethanol (7568-93-6) → 2-{[(4-chlorophenyl)methylidene]amino}-1-phenylethan-1-ol

Conditions	Yield
In methanol at 20℃; for 0.0833333h; Solvent;	99%

2-methoxycinnamaldehyde (1504-74-1) + 2-Amino-1-phenylethanol (7568-93-6) → 2-{[3-(2-methoxyphenyl)prop-2-en-1-ylidene]amino}-1-phenylethan-1-ol

Conditions	Yield
In methanol at 20℃; for 0.0833333h;	99%

2,6-dichloro-pyridine-3-carbaldehyde (55304-73-9) + 2-Amino-1-phenylethanol (7568-93-6) → 2-((2,6-dichloropyridin-3-yl)methylamino)-1-phenylethanol (1255701-31-5)

Conditions	Yield
Stage #1: 2,6-dichloro-pyridine-3-carbaldehyde; 2-Amino-1-phenylethanol In methanol at 20℃; for 2h; Stage #2: With sodium cyanoborohydride In methanol for 0.5h;	98.2%

benzoyl cyanide (613-90-1) + 2-Amino-1-phenylethanol (7568-93-6) → 2-(benzoylamino)-1-phenylethanol (34119-82-9)

Conditions	Yield
In dichloromethane for 15h; Ambient temperature;	98%

formaldehyd (50-00-0) + Glyoxal (131543-46-9) + 2-Amino-1-phenylethanol (7568-93-6) → 1-phenyl-2-(1-imidazolyl)ethanol (24155-47-3, 27656-18-4)

Conditions	Yield
With ammonium chloride In methanol at 80℃;	98%

2-cyano-1-phenylacetylene (935-02-4) + 2-Amino-1-phenylethanol (7568-93-6) → (E)-3-(2-Hydroxy-2-phenyl-ethylamino)-3-phenyl-acrylonitrile

Conditions	Yield
	97%

4-methoxy-benzaldehyde (123-11-5) + 2-Amino-1-phenylethanol (7568-93-6) → 2-phenyl-N-(4'-methoxybenzylidene)ethanolamine (101067-50-9)

Conditions	Yield
Heating;	97%

p-toluenesulfonyl chloride (98-59-9) + 2-Amino-1-phenylethanol (7568-93-6) → (R)-N-(2-hydroxy-2-phenylethyl)-4-methylbenzenesulfonamide (149286-01-1)

Conditions	Yield
With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 3h; stereoselective reaction;	97%

oxalic acid diethyl ester (95-92-1) + 2-Amino-1-phenylethanol (7568-93-6) → N,N'-bis-(2-hydroxy-2-phenyl-ethyl)-oxalamide

Conditions	Yield
In toluene at 20℃; for 24h; Solvent;	96%

2-((4-chlorobenzyl)oxy)-1-naphthaldehyde + 2-Amino-1-phenylethanol (7568-93-6) → 2-(((2-((4-chlorobenzyl)oxy)naphthalen-1-yl)methyl)amino)-1-phenylethan-1-ol

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; for 2.5h;	96%

5-chloro-N-(1-cyclopropyl-2,2,2-trifluoroethyl)-7-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide + 2-Amino-1-phenylethanol (7568-93-6) → N-(1-cyclopropyl-2,2,2-trifluoroethyl)-5-(2-hydroxy-2-phenylethylamino)-7-methylpyrazolo[1,5-a]pyrimidine-3-carboxamide

Conditions	Yield
With triethylamine In acetonitrile at 80℃; for 2h;	96%

carbon monoxide (201230-82-2) + 2-Amino-1-phenylethanol (7568-93-6) → N-(2-hydroxy-2-phenylethyl)formamide (58644-57-8)

Conditions	Yield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine In toluene at 100℃; under 22502.3 Torr; for 20h; Autoclave;	96%

p-toluenesulfonyl chloride (98-59-9) + 2-Amino-1-phenylethanol (7568-93-6) → 2-(N-tosylamino)-1-phenyl-1-ethanol (149286-01-1, 149342-45-0, 35550-09-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 25℃; for 16h;	95%
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere;	94%
With triethylamine In dichloromethane at 0 - 20℃; for 18h;	78%

Upstream product

• 613-90-1 benzoyl cyanide 
• 96-09-3 styrene oxide 
• 4937-87-5 N-hydroxy-2-oxo-2-phenylethanimidoyl chloride 
• 24506-17-0 3-hydroxy-3-phenylpropionamide 
• 75-52-5 nitromethane 
• 100-52-7 benzaldehyde 
• 614-21-1 2-nitroacetophenone 
• 64-04-0 phenethylamine 
• 57402-97-8 N-<(trimethylsilyl)methyl>benzaldimine 
• 91994-49-9 2,2,2-trifluoro-N-(2-oxo-2-phenylethyl)acetamide 
• 88626-81-7 C₂₅H₂₁N₃O₃Si 
• 91994-60-4 N-(2-hydroxy-2-phenylethyl)-2,2,2-trifluoroacetylamide 
• 69-96-5 dl-threo-phenylserine 
• 51411-44-0 2-diphenylmethylenamino-1-phenylethanol 

Downstream Products

• 79365-85-8 bis-(β-hydroxy-phenethyl)-amine 
• 110057-85-7 tris-(β-hydroxy-phenethyl)-amine 
• 22020-69-5 oxytriphine 
• 59801-46-6 2-(1,1-dioxo-1λ⁶-thiomorpholin-4-yl)-1-phenyl-ethanol 
• 24703-90-0 5-methyl-5'-phenyl-2λ⁵-spiro[benzo[1,3,2]dioxaphosphole-2,2'-[1,3,2]oxazaphospholidine] 
• 3306-05-6 N-(2-hydroxy-2-phenylethyl)acetamide 
• 55111-96-1 2-[5-(2-diethylamino-ethylidene)-4,5-dihydro-thiazol-2-ylamino]-1-phenyl-ethanol 
• 60159-71-9 2,10a-diphenyl-2,3,10,10a-tetrahydro-oxazolo[3,2-b]isoquinolin-5-one 
• 47556-93-4 3-Methyl-but-2-enoic acid {3-[3-(2-hydroxy-2-phenyl-ethylamino)-propionyl]-phenyl}-amide 
• 55848-61-8 2-phenyl-2-(trimethylsiloxy)ethylamine 
• 2207-50-3 2-amino-5-phenyl-2-oxazoline 
• 53828-49-2 2-phenyl-[1,4]oxazepane-5,7-dione 
• 56202-94-9 1-phenyl-2-(1-methyl-2-phenylacetamidoethyl)aminoethanol 
• 51321-93-8 5-acetyl-2-phenyl-3,4-dihydro-2H-benzo[1,4]oxazine-6,7-dione 

Relevant articles and documents

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