Product Name

  • Name

    2-Aminophenethanol

  • EINECS 226-275-9
  • CAS No. 5339-85-5
  • Article Data19
  • CAS DataBase
  • Density 1.124 g/cm3
  • Solubility soluble in cold water
  • Melting Point 89oC
  • Formula C8H11NO
  • Boiling Point 306.661 °C at 760 mmHg
  • Molecular Weight 137.181
  • Flash Point 127.913 °C
  • Transport Information
  • Appearance viscous liquid
  • Safety 26-37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 5339-85-5 (2-Aminophenethanol)
  • Hazard Symbols IrritantXi
  • Synonyms Phenethylalcohol, o-amino- (6CI,7CI,8CI);2-(2-Aminophenyl)ethanol;2-(2-Aminophenyl)ethyl alcohol;2-(2-Hydroxyethyl)aniline;2-(o-Aminophenyl)ethanol;2-Aminophenethyl alcohol;2-Aminophenylethyl alcohol;NSC 3572;[2-(2-Hydroxyethyl)phenyl]amine;o-Aminophenethyl alcohol;
  • PSA 46.25000
  • LogP 1.38480

Synthetic route

2-nitro-benzeneethanol
15121-84-3

2-nitro-benzeneethanol

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
100%
100%
100%
2-(2-nitrophenyl)ethyl nitrate
833-44-3

2-(2-nitrophenyl)ethyl nitrate

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
With hydrogen; palladium/alumina
formaldehyd
50-00-0

formaldehyd

1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
With N-benzyl-trimethylammonium hydroxide; calcium chloride; zinc 1.) Me2SO, 95 deg C, 1 h, 2.) H2O, reflux; Multistep reaction;
2-nitro-benzeneethanol
15121-84-3

2-nitro-benzeneethanol

water
7732-18-5

water

zinc dust

zinc dust

calcium chloride

calcium chloride

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

...Expand
carbon monoxide
201230-82-2

carbon monoxide

2-nitro-benzeneethanol
15121-84-3

2-nitro-benzeneethanol

A

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

B

4,5-dihydro-3,1-benzoxazepin-2(1H)-one

4,5-dihydro-3,1-benzoxazepin-2(1H)-one

Conditions
ConditionsYield
With 1-Methylpyrrolidine; selenium In tetrahydrofuran at 150℃; under 22800 Torr; for 5h;A n/a
B 66 % Chromat.
...Expand
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 37 percent / sodium phenoxide / dimethylsulfoxide / 1 h / 60 - 67 °C
2: 78 percent / calcium chloride; zinc powder / H2O / 0.5 h / Heating
View Scheme
Multi-step reaction with 2 steps
1: sodium hydroxide / 1.5 h / pH 7.4 / Large scale reaction
2: hydrogen / paraffin oil / 1.5 h / 110 °C / 15001.5 Torr
View Scheme
Multi-step reaction with 2 steps
1: sodium phenoxide / dimethyl sulfoxide / 1 h / 60 - 67 °C
2: zinc; calcium chloride / water / 0.5 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: potassium hydroxide / water; dimethyl sulfoxide / 1 h / 0 - 20 °C / Inert atmosphere
2: hydrogen; palladium 10% on activated carbon / methanol / 20.5 h / 20 °C / 760.05 Torr / Inert atmosphere
View Scheme
acetic acid phenethyl ester
103-45-7

acetic acid phenethyl ester

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid anhydride; nitric acid / 35 - 40 °C / Kochen des Reaktionsprodukts mit methanol. HCl
2: zinc; aqueous calcium chloride
View Scheme
2-(2-nitrophenyl)acetic acid
3740-52-1

2-(2-nitrophenyl)acetic acid

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: borane-THF
2: zinc; calcium chloride; water
View Scheme
Multi-step reaction with 2 steps
1: lithium aluminium tetrahydride / methanol
2: 10% Pd/C; hydrogen / ethanol
View Scheme
2-oxoindole
59-48-3

2-oxoindole

A

1-indoline
496-15-1

1-indoline

B

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
With tris(2,4-pentanedionato)ruthenium(III); ytterbium(III) trifluoromethanesulfonate nonohydrate; hydrogen; [2-((diphenylphospino)methyl)-2-methyl-1,3-propanediyl]bis[diphenylphosphine] In tetrahydrofuran at 150℃; under 37503.8 Torr; for 15h; Autoclave;A 61 %Chromat.
B n/a
methyl (2-nitrophenyl)acetate
30095-98-8

methyl (2-nitrophenyl)acetate

A

indole
120-72-9

indole

B

2-oxoindole
59-48-3

2-oxoindole

C

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

D

2-aminophenylacetic acid methyl ester
35613-44-6

2-aminophenylacetic acid methyl ester

Conditions
ConditionsYield
With sodium tetrahydroborate In tetrahydrofuran; water at 20℃; for 12h; Sonication; chemoselective reaction;
...Expand
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

indole
120-72-9

indole

Conditions
ConditionsYield
100%
100%
With C21H28I3IrN6Pd; potassium hydroxide In toluene at 110℃; for 2h; Reagent/catalyst; Inert atmosphere; Schlenk technique;99%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2-tert-butyldiphenylsilyloxyethylaniline
931105-21-4

2-tert-butyldiphenylsilyloxyethylaniline

Conditions
ConditionsYield
With sodium hydride In tetrahydrofuran at 0℃; for 17h;100%
5-bromovaleroyl chloride
4509-90-4

5-bromovaleroyl chloride

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

5-bromo-N-[2-(2-hydroxyethyl)phenyl]pentanamide
1430091-95-4

5-bromo-N-[2-(2-hydroxyethyl)phenyl]pentanamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at -5 - 0℃;100%
With triethylamine In dichloromethane at -5 - 0℃;100%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

2-ethyl ethyl carbonate

2-ethyl ethyl carbonate

Conditions
ConditionsYield
With potassium carbonate In acetone for 2h; Heating;97%
triethylsilyl chloride
994-30-9

triethylsilyl chloride

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

O-triethylsilyl-2-(o-aminophenyl)ethanol
163531-18-8

O-triethylsilyl-2-(o-aminophenyl)ethanol

Conditions
ConditionsYield
With triethylamine97%
With triethylamine In dichloromethane at -20℃; for 1h;97%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2-benzoyl-4,5-dichloropyridazin-3(2H)-one
155164-66-2

2-benzoyl-4,5-dichloropyridazin-3(2H)-one

benzoic acid-[2-(2-hydroxy-ethyl)-anilide]
364607-96-5

benzoic acid-[2-(2-hydroxy-ethyl)-anilide]

Conditions
ConditionsYield
In tetrahydrofuran at 18℃; for 18h;97%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

trifluoroacetic acid
76-05-1

trifluoroacetic acid

2,2,2-trifluoro-1-(indolin-1-yl)ethan-1-one
90732-28-8

2,2,2-trifluoro-1-(indolin-1-yl)ethan-1-one

Conditions
ConditionsYield
With tetrachloromethane; triethylamine; triphenylphosphine Heating;97%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

carbonic acid dimethyl ester
616-38-6

carbonic acid dimethyl ester

2,3-dihydroindole-1-carboxylic acid methyl ester
89875-37-6

2,3-dihydroindole-1-carboxylic acid methyl ester

Conditions
ConditionsYield
With 1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine at 90℃; for 21h; Reagent/catalyst; Time;97%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

1-indoline
496-15-1

1-indoline

Conditions
ConditionsYield
Stage #1: 2-aminophenethyl alcohol With thionyl chloride In 1,2-dimethoxyethane at 20℃;
Stage #2: In 1,2-dimethoxyethane; water at 60℃; Further stages.;		94%
With sodium hydroxide; benzenesulfonyl chloride
With zinc(II) chloride at 200℃;
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2-acetyl-4,5-dichloropyridazin-3(2H)-one
155164-63-9

2-acetyl-4,5-dichloropyridazin-3(2H)-one

2-(2-acetylaminophenyl)ethyl alcohol
69258-86-2

2-(2-acetylaminophenyl)ethyl alcohol

Conditions
ConditionsYield
In tetrahydrofuran at 17℃; for 0.2h;94%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2,3-Dioxo-pent-4-enoic acid tert-butyl ester
117917-40-5

2,3-Dioxo-pent-4-enoic acid tert-butyl ester

3-oxo-2,3,5,6-tetrahydro-1H-4-oxa-10b-aza-benzo[e]azulene-3a-carboxylic acid tert-butyl ester

3-oxo-2,3,5,6-tetrahydro-1H-4-oxa-10b-aza-benzo[e]azulene-3a-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
94%
Difluoroacetic acid
381-73-7

Difluoroacetic acid

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

N-difluoroacetylindoline

N-difluoroacetylindoline

Conditions
ConditionsYield
With tetrachloromethane; triethylamine; triphenylphosphine Heating;94%
5-chloro-1H-Indole-2-carboxylic acid
10517-21-2

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

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

C17H15ClN2O2
1036750-32-9

C17H15ClN2O2

Conditions
ConditionsYield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 14h;94%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

4-methyl-benzaldehyde
104-87-0

4-methyl-benzaldehyde

2-(4-methylphenyl)quinoline
24667-94-5

2-(4-methylphenyl)quinoline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; silver trifluoromethanesulfonate In toluene at 120℃; for 12h; Green chemistry;94%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

salicylaldehyde
90-02-8

salicylaldehyde

2-<<(2-hydroxyphenyl)methylene>imino>benzeneethanol

2-<<(2-hydroxyphenyl)methylene>imino>benzeneethanol

Conditions
ConditionsYield
In benzene for 0.5h; Heating;93%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

4,5-Dichloro-2-(4-methoxy-benzoyl)-2H-pyridazin-3-one
155164-68-4

4,5-Dichloro-2-(4-methoxy-benzoyl)-2H-pyridazin-3-one

N-[2-(2-hydroxy-ethyl)-phenyl]-4-methoxy-benzamide

N-[2-(2-hydroxy-ethyl)-phenyl]-4-methoxy-benzamide

Conditions
ConditionsYield
In tetrahydrofuran at 18℃; for 7h;93%
3-(3-hydroxy-6-methylpyridin-2-ylmethyl)-2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazole-5-carbaldehyde
857070-65-6

3-(3-hydroxy-6-methylpyridin-2-ylmethyl)-2-(3-morpholin-4-ylpropylamino)-3H-benzoimidazole-5-carbaldehyde

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

C30H38N6O3

C30H38N6O3

Conditions
ConditionsYield
With acetic acid In methanol at 20℃; for 16h;93%
2-isocyanobenzaldehyde
1101183-58-7

2-isocyanobenzaldehyde

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2,3-dihydro-14bH-benzo[4,5][1,3]oxazepino[3,2-c]quinazoline

2,3-dihydro-14bH-benzo[4,5][1,3]oxazepino[3,2-c]quinazoline

Conditions
ConditionsYield
With pyridinium p-toluenesulfonate In dimethyl sulfoxide at 25℃; Molecular sieve;93%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

benzyl alcohol
100-51-6

benzyl alcohol

indole
120-72-9

indole

Conditions
ConditionsYield
With [RuCl2(2-diphenylphosphinoethylamine)2]; potassium tert-butylate; zinc(II) trifluoroacetate In 1,4-dioxane for 18h; Reagent/catalyst; Reflux;91%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

N-(2-(2-hydroxyethyl)phenyl)methanesulfonamide

N-(2-(2-hydroxyethyl)phenyl)methanesulfonamide

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 25℃;91%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2-(2-((tert-butoxycarbonyl)amino)phenyl)ethanol
193806-49-4

2-(2-((tert-butoxycarbonyl)amino)phenyl)ethanol

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water for 4h; Ambient temperature;90%
With sodium hydrogencarbonate In 1,4-dioxane72%
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;
Burgess Reagent
29684-56-8

Burgess Reagent

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

6,6-dioxo-5,6,8,9-tetrahydro-6λ6-thia-5,7-diaza-benzocycloheptene-7-carboxylic acid methyl ester

6,6-dioxo-5,6,8,9-tetrahydro-6λ6-thia-5,7-diaza-benzocycloheptene-7-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating;90%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

6,6-dioxo-5,6,8,9-tetrahydro-6λ6-thia-5,7-diaza-benzocycloheptene-7-carboxylic acid methyl ester

6,6-dioxo-5,6,8,9-tetrahydro-6λ6-thia-5,7-diaza-benzocycloheptene-7-carboxylic acid methyl ester

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating / reflux;90%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

benzaldehyde
100-52-7

benzaldehyde

2-Phenylquinoline
612-96-4

2-Phenylquinoline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; silver trifluoromethanesulfonate In toluene at 120℃; for 12h; Green chemistry;89%
Multi-step reaction with 2 steps
1: 0.08 h / 100 °C
2: silver trifluoromethanesulfonate; trifluorormethanesulfonic acid; oxygen / toluene / 12 h / 120 °C
View Scheme
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

2-vinylaniline
3867-18-3

2-vinylaniline

Conditions
ConditionsYield
With potassium hydroxide88%
With potassium hydroxide at 180℃; under 0.25 Torr; for 4h;78%
With potassium hydroxide at 180℃; under 0.05 Torr; for 4h;75%
2-Nitrobenzyl alcohol
612-25-9

2-Nitrobenzyl alcohol

2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

5,6-dihydrobenzo[4,5][1,3]oxazepino[3,2-b]indazole

5,6-dihydrobenzo[4,5][1,3]oxazepino[3,2-b]indazole

Conditions
ConditionsYield
With sulfuric acid In isopropyl alcohol at 25℃; for 4h; UV-irradiation;87%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

methyl iodide
74-88-4

methyl iodide

2-(2-dimethylaminophenyl)ethyl alcohol
5339-27-5

2-(2-dimethylaminophenyl)ethyl alcohol

Conditions
ConditionsYield
Stage #1: 2-aminophenethyl alcohol With potassium carbonate In acetonitrile at 20℃; for 0.666667h;
Stage #2: methyl iodide In acetonitrile for 3h; Reflux;		86.3%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

m-tolyl aldehyde
620-23-5

m-tolyl aldehyde

2-(m-tolyl)quinoline
24641-30-3

2-(m-tolyl)quinoline

Conditions
ConditionsYield
With trifluorormethanesulfonic acid; silver trifluoromethanesulfonate In toluene at 120℃; for 12h; Green chemistry;84%
2-aminophenethyl alcohol
5339-85-5

2-aminophenethyl alcohol

benzoic acid
65-85-0

benzoic acid

N-benzoylindoline
61589-14-8

N-benzoylindoline

Conditions
ConditionsYield
With tetrachloromethane; triethylamine; triphenylphosphine Heating;83%

2-Aminophenethanol Specification

The 2-Aminophenethanol, with the CAS registry number 5339-85-5, is also known as o-Aminophenethyl alcohol. It belongs to the product categories of Naphthyridine,Quinoline; Amino Alcohols; Organic Building Blocks; Oxygen Compounds. Its EINECS number is 226-275-9. This chemical's molecular formula is C8H11NO and molecular weight is 137.18. What's more, its systematic name is 2-(2-Aminophenyl)ethanol. This chemical should be sealed and stored in a dry place. Moreover, it should be protected from light and oxidants. It is used in organic synthesis.

Physical properties of 2-Aminophenethanol are: (1)ACD/LogP: 0.17; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 0.14; (4)ACD/LogD (pH 7.4): 0.17; (5)ACD/BCF (pH 5.5): 1.00; (6)ACD/BCF (pH 7.4): 1.00; (7)ACD/KOC (pH 5.5): 27.67; (8)ACD/KOC (pH 7.4): 29.45; (9)#H bond acceptors: 2; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 4; (12)Polar Surface Area: 46.25 Å2; (13)Index of Refraction: 1.597; (14)Molar Refractivity: 41.573 cm3; (15)Molar Volume: 122.037 cm3; (16)Polarizability: 16.481×10-24cm3; (17)Surface Tension: 51.19 dyne/cm; (18)Density: 1.124 g/cm3; (19)Flash Point: 127.913 °C; (20)Enthalpy of Vaporization: 57.778 kJ/mol; (21)Boiling Point: 306.661 °C at 760 mmHg; (22)Vapour Pressure: 0 mmHg at 25°C.

Uses of 2-Aminophenethanol: it can be used to produce 2-(2-triethylsilanyloxy-ethyl)-phenylamine at the temperature of -20 °C. It will need reagent Et3N and solvent CH2Cl2 with the reaction time of 1 hour. The yield is about 97%.

2-Aminophenethanol can be used to produce 2-(2-triethylsilanyloxy-ethyl)-phenylamine at the temperature of -20 °C

When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. In case of contact with eyes, you should rinse immediately with plenty of water and seek medical advice. When using it, you need to wear suitable protective gloves and eye/face protection.

You can still convert the following datas into molecular structure:
(1)SMILES: OCCc1ccccc1N
(2)Std. InChI: InChI=1S/C8H11NO/c9-8-4-2-1-3-7(8)5-6-10/h1-4,10H,5-6,9H2
(3)Std. InChIKey: ILDXSRFKXABMHH-UHFFFAOYSA-N 

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