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5339-85-5

Basic Information
CAS No.: 5339-85-5
Name: Benzeneethanol, 2-amino-
Molecular Structure:
Molecular Structure of 5339-85-5 (Benzeneethanol, 2-amino-)
Formula: C8H11NO
Molecular Weight: 137.18
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;
EINECS: 226-275-9
Density: 1.124 g/cm3
Melting Point: 89oC
Boiling Point: 306.661 °C at 760 mmHg
Flash Point: 127.913 °C
Solubility: soluble in cold water
Appearance: viscous liquid
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 26-37/39
Transport Information:
PSA: 46.25000
LogP: 1.38480
Synthetic route
15121-84-3

2-nitro-benzeneethanol

5339-85-5

2-aminophenethyl alcohol

Conditions
ConditionsYield
100%
100%
100%
833-44-3

2-(2-nitrophenyl)ethyl nitrate

5339-85-5

2-aminophenethyl alcohol

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

formaldehyd

88-72-2

1-methyl-2-nitrobenzene

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;
15121-84-3

2-nitro-benzeneethanol

zinc dust

zinc dust

calcium chloride

calcium chloride

5339-85-5

2-aminophenethyl alcohol

201230-82-2

carbon monoxide

15121-84-3

2-nitro-benzeneethanol

A

5339-85-5

2-aminophenethyl alcohol

B

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.
88-72-2

1-methyl-2-nitrobenzene

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
103-45-7

acetic acid phenethyl ester

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
3740-52-1

2-(2-nitrophenyl)acetic acid

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
59-48-3

2-oxoindole

A

496-15-1

1-indoline

B

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
30095-98-8

methyl (2-nitrophenyl)acetate

A

120-72-9

indole

B

59-48-3

2-oxoindole

C

5339-85-5

2-aminophenethyl alcohol

D

35613-44-6

2-aminophenylacetic acid methyl ester

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

2-aminophenethyl alcohol

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%
5339-85-5

2-aminophenethyl alcohol

931105-21-4

2-tert-butyldiphenylsilyloxyethylaniline

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

5-bromovaleroyl chloride

5339-85-5

2-aminophenethyl alcohol

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%
5339-85-5

2-aminophenethyl alcohol

541-41-3

chloroformic acid ethyl ester

2-ethyl ethyl carbonate

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

triethylsilyl chloride

5339-85-5

2-aminophenethyl alcohol

163531-18-8

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

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

2-aminophenethyl alcohol

155164-66-2

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

364607-96-5

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

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

2-aminophenethyl alcohol

76-05-1

trifluoroacetic acid

90732-28-8

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

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

2-aminophenethyl alcohol

616-38-6

carbonic acid dimethyl 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%
5339-85-5

2-aminophenethyl alcohol

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℃;
5339-85-5

2-aminophenethyl alcohol

155164-63-9

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

69258-86-2

2-(2-acetylaminophenyl)ethyl alcohol

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

2-aminophenethyl alcohol

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

Conditions
ConditionsYield
94%
381-73-7

Difluoroacetic acid

5339-85-5

2-aminophenethyl alcohol

N-difluoroacetylindoline

Conditions
ConditionsYield
With tetrachloromethane; triethylamine; triphenylphosphine Heating;94%
10517-21-2

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

5339-85-5

2-aminophenethyl alcohol

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%
5339-85-5

2-aminophenethyl alcohol

104-87-0

4-methyl-benzaldehyde

24667-94-5

2-(4-methylphenyl)quinoline

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

2-aminophenethyl alcohol

90-02-8

salicylaldehyde

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

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

2-aminophenethyl alcohol

155164-68-4

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

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

Conditions
ConditionsYield
In tetrahydrofuran at 18℃; for 7h;93%
857070-65-6

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

5339-85-5

2-aminophenethyl alcohol

C30H38N6O3

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

2-isocyanobenzaldehyde

5339-85-5

2-aminophenethyl alcohol

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%
5339-85-5

2-aminophenethyl alcohol

100-51-6

benzyl alcohol

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%
5339-85-5

2-aminophenethyl alcohol

124-63-0

methanesulfonyl chloride

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

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

di-tert-butyl dicarbonate

5339-85-5

2-aminophenethyl alcohol

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℃;
29684-56-8

Burgess Reagent

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

Conditions
ConditionsYield
In tetrahydrofuran for 2h; Heating;90%
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

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

2-aminophenethyl alcohol

100-52-7

benzaldehyde

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
5339-85-5

2-aminophenethyl alcohol

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%
612-25-9

2-Nitrobenzyl alcohol

5339-85-5

2-aminophenethyl alcohol

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%
5339-85-5

2-aminophenethyl alcohol

74-88-4

methyl iodide

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%
5339-85-5

2-aminophenethyl alcohol

620-23-5

m-tolyl aldehyde

24641-30-3

2-(m-tolyl)quinoline

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

2-aminophenethyl alcohol

65-85-0

benzoic acid

61589-14-8

N-benzoylindoline

Conditions
ConditionsYield
With tetrachloromethane; triethylamine; triphenylphosphine Heating;83%
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  • 2-Aminophenethanol

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    5339-85-5

    2-Aminophenethanol

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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