104-10-9

Basic information

• Product Name: 2-(4-Aminophenyl)ethanol
• Synonyms: B-(P-AMINOPHENYL)ETHANOL;2-(P-AMINOPHENYL)ETHANOL;2-(4-AMINOPHENYL)ETHANOL;2-(4-AMINOPHENYL)ETHYL ALCOHOL;4-AMINOPHENETHYL ALCOHOL;4-AMINOPHENYLETHYL ALCOHOL;AKOS BBS-00006893;P-AMINOPHENETHYL ALCOHOL
• CAS NO: 104-10-9
• Molecular Formula: C₈H₁₁NO
• Molecular Weight: 137.18
• EINECS: 203-174-8
• Product Categories: Benzhydrols, Benzyl & Special Alcohols;Amines;Miscellaneous;Amino Alcohols;Organic Building Blocks;Oxygen Compounds
• Mol File: 104-10-9.mol
• Article Data: 39

Chemical Properties

• Melting Point: 107-110 °C(lit.)
• Boiling Point: 255 °C
• Flash Point: 127.7 °C
• Appearance: Light brown to brown/Crystals
• Density: 1.0630 (rough estimate)
• Vapor Pressure: 0.00115mmHg at 25°C
• Refractive Index: 1.5470 (estimate)
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• Solubility: Soluble in methanol.
• PKA: 15.05±0.10(Predicted)
• BRN: 907205
• CAS DataBase Reference: 2-(4-Aminophenyl)ethanol(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Aminophenyl)ethanol(104-10-9)
• EPA Substance Registry System: 2-(4-Aminophenyl)ethanol(104-10-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-24/25
• WGK Germany: 3
• F: 10-23
• TSCA: T
• HazardClass: IRRITANT
• Hazardous Substances Data: 104-10-9(Hazardous Substances Data)

Usage

Description

2-(4-Aminophenyl)ethanol, also known as 4-Aminophenethyl alcohol, is an organic compound with the chemical formula C8H11NO. It is characterized by its light brown to brown crystalline appearance. This versatile molecule is known for its various applications in different industries, particularly in the synthesis of polymers, organic compounds, and the functionalization of materials.

Uses

Used in Polymer Synthesis:
2-(4-Aminophenyl)ethanol is used as a nonsymmetric monomer for the preparation of ordered poly(amide-ester) structures. These polymers can be arranged in either head-to-head (H-H) or tail-to-tail (T-T) configurations, which can influence the properties and performance of the resulting materials.
Used in Chemical Synthesis:
In the chemical synthesis industry, 2-(4-Aminophenyl)ethanol serves as a key component in the synthesis of 4-aminostyrene, an important organic compound with various applications in the production of dyes, pharmaceuticals, and other specialty chemicals.
Used in Material Functionalization:
2-(4-Aminophenyl)ethanol is also utilized in the functionalization of graphene nanoplatelets. This process involves the attachment of specific functional groups to the surface of graphene, which can enhance its properties and make it suitable for a wide range of applications, such as in electronics, energy storage, and composite materials.

Synthesis Reference(s)

Journal of the American Chemical Society, 72, p. 1361, 1950 DOI: 10.1021/ja01159a077

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

Synthetic route

2-(4-nitrophenyl)ethanol (100-27-6) → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With hydrogenchloride; hydrazine hydrate; sodium hydroxide In methanol; water at 68℃; pH=7; Reagent/catalyst; pH-value;	99.7%
With hydrogenchloride; indium In tetrahydrofuran at 20℃; for 1.5h;	98%
With cerium(IV) oxide; hydrogen; manganese(II) oxide; zinc(II) oxide In ethanol at 80℃; under 760.051 Torr;	98.3%

methyl (4-(2-hydroxyethyl)phenyl)carbamate → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With 3-azapentane-1,5-diamine at 130℃; for 12h; Sealed tube;	99%

β-(2,4-dinitrophenyl)ethyl nitrate (1081-79-4) → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With 5%-palladium/activated carbon; hydrogen In isopropyl alcohol at 40℃; for 3h; Temperature; Time;	95.7%
With hydrazine hydrate In methanol Heating;	83%
With hydrogen; palladium/alumina In methanol
With hydrogen; nickel at 18 - 25℃; under 3800 - 22800 Torr; Catalytic hydrogenation;

(4-azidophenyl)-2-ethanol → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With formic acid; tris(2,2'-bipyridyl)ruthenium dichloride; diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; N-ethyl-N,N-diisopropylamine In dichloromethane at 25℃; Irradiation; chemoselective reaction;	90%

methyl {4-[2-(triisopropylsilyloxy)ethyl]phenyl}carbamate → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With hydrazine hydrate; potassium hydroxide In ethylene glycol at 200℃; for 1.5h; Sealed tube;	84%

{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With indium; ammonium chloride In ethanol for 1.5h; Heating;	78%

ethyl (4-amino-3,5-dibromophenyl)acetate (5438-70-0) → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;	78%

2-phenylethanol (60-12-8) → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With CH5NO3S*CHF3O3S; iron(II) sulfate In water; acetonitrile at 20℃; for 16h;	65%
Multi-step reaction with 2 steps 1: nitric acid / water / -10 - 0 °C 2: hydrogen; 5%-palladium/activated carbon / isopropyl alcohol / 3 h / 40 °C View Scheme

{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-phenyl}-carbamic acid 2,2,2-trichloro-ethyl ester → 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)aniline (173901-21-8) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With acetic acid; zinc for 24h;	A 61% B n/a

p-Nitrophenyloxirane (6388-74-5) → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With aluminum oxide; sodium tetrahydroborate; palladium dichloride In hexane; water at 60℃; for 3h;	54%

ETHYL 4-NITROPHENYLACETATE (5445-26-1) → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere;	36%

acetic acid phenethyl ester (103-45-7) → 2-(4'-aminophenyl)ethyl alcohol (104-10-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) H2SO4, HNO3; 2.) HCl / 1.) acetic anhydride, -15 deg C, 105 min; 2.) methanol, reflux, 3.5 h 2: 16.2 g / H2 / PtO2 / aq. ethanol View Scheme
Multi-step reaction with 2 steps 1: nitric acid / -15 °C / Verseifung des entstandenen Acetats mit methylalkoholischer Salzsaeure 2: zinc; calcium chloride View Scheme

acetic anhydride (108-24-7) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-(4-Acetamidophenyl)ethyl acetate (75178-16-4)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 14h; Inert atmosphere;	100%
With triethylamine	94%
With dmap

2-(4'-aminophenyl)ethyl alcohol (104-10-9) + 4-(6-methyl-3-oxo-4-(3-(trifluoromethyl)phenyl)-3,6-dihydrodipyrazolo[3,4-b:3',4'-d]pyridin-2(1H)-yl)benzoic acid (635324-87-7) → N-[4-(2-hydroxyethyl)phenyl]-4-(6-methyl-3-oxo-4-[3-(trifluoromethyl)phenyl]-3,6-dihydrodipyrazolo[3,4-b:3,4-d]pyridin-2(1H)-yl)benzamide

Conditions	Yield
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 16h;	100%

di-tert-butyl dicarbonate (24424-99-5) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → tert-butyl N-[4-(2-hydroxyethyl)phenyl]carbamate (104060-23-3)

Conditions	Yield
In tetrahydrofuran at 0 - 20℃; for 16h;	100%
In ethyl acetate at 20℃; for 48h;	99%
In ethyl acetate at 20℃; for 24h;	99%

2-bromo-1-phenyl-1-propanone (2114-00-3) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-{[4-(2-hydroxyethyl)phenyl]amino}-1-phenyl-1-propanone (616893-32-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 72h;	100%

triethyl borate (150-46-9) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → B(OCH2CH2C6H4NH2)3 (76644-60-5)

Conditions	Yield
In benzene byproducts: ethanol; molar ratio B(OEt)3:alcohol=1:3, refluxing; distn. (reduced pressure); elem. anal.;	100%

hexakis[μ-(2-propanolato)]hexakis(2-propanolato)tetraaluminum (25443-56-5) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → Al(3+)*OCH(CH3)2(1-)*2OCH2CH2C6H4NH2(1-)=Al(OCH(CH3)2)(OCH2CH2C6H4NH2)2

Conditions	Yield
In benzene to aluminium isopropoxide added p-aminophenyl alcohol (molar ratio 1:2), followed by benzene, contents shaken and refluxed for 18 h; excess benzene removed by pump at room temp.; elem. anal.;	100%

acetylacetone (123-54-6) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-[4-(3,5-dimethyl-1H-pyrazol-1-yl)phenyl]ethanol

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)ethyl alcohol With hydrogenchloride; sodium nitrate; tin(ll) chloride In water at -10 - 20℃; for 2.5h; Stage #2: acetylacetone In water at 100℃; for 5h;	100%

1-(3-hydroxypropyl)-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile (98458-25-4) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-hydroxy-3-[4-(2-hydroxyethyl)-phenylazo]-1-(3-hydroxypropyl)-4-methyl-2-oxo-1,6-dihydropyridine-5-carbonitrile (1357264-73-3)

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)ethyl alcohol With hydrogenchloride; sodium nitrite In water for 0.5h; Cooling with ice; Stage #2: 1-(3-hydroxypropyl)-6-hydroxy-4-methyl-2-oxo-1,2-dihydropyridine-3-carbonitrile With aminosulfonic acid In water pH=2 - 2.5;	100%

2-(4'-aminophenyl)ethyl alcohol (104-10-9) → (4-azidophenyl)-2-ethanol

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)ethyl alcohol With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Stage #2: With sodium azide In water at 0℃; for 1.5h;	100%
Stage #1: 2-(4'-aminophenyl)ethyl alcohol With hydrogenchloride; sodium nitrite In water at 0℃; for 0.5h; Inert atmosphere; Stage #2: With sodium azide In water at 0℃; for 1h; Inert atmosphere;

2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 3,5-dibromo-4-aminophenethyl alcohol (184769-87-7)

Conditions	Yield
With bromine In acetic acid at 25℃; for 0.5h; Bromination;	99%
With bromine; acetic acid at 25℃; for 0.5h; Bromination;	99%
With tetra-N-butylammonium tribromide; calcium carbonate In methanol; dichloromethane at 20℃; for 2.5h;	90%
With bromine In tetrahydrofuran at 0℃; for 0.0833333h; Yield given;
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 4h;

ethyl bromoacetate (105-36-2) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → ethyl N-ethyloxycarbonylmethyl-N-[4-(2-hydroxyethyl)phenyl]aminoacetate (344285-87-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20 - 70℃; for 1h;	99%

salicylaldehyde (90-02-8) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 4-(salicylideneamino)phenethyl alcohol (424836-20-4)

Conditions	Yield
In ethanol	99%

2,2,2-trifluoroethyl benzoate (1579-72-2) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 4-aminophenethyl benzoate (858855-90-0)

Conditions	Yield
With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] In toluene at 120℃; for 2h; Inert atmosphere; Schlenk technique; chemoselective reaction;	99%
With [1,3-bis(2,4,6-trimethylphenyl)imidazol]-2-ylidene In tetrahydrofuran at 20℃; for 24h; Reagent/catalyst; chemoselective reaction;	98%

Nitrosobenzene (586-96-9) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → p-(phenylazo)phenethyl alcohol

Conditions	Yield
With acetic acid In dichloromethane	99%

2-chlorothiazole (3034-52-4) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → C11H12N2OS

Conditions	Yield
With C50H61Cl2N3Pd; potassium tert-butylate In 1,4-dioxane at 100℃; for 2h;	99%

BARBITURIC ACID (67-52-7) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → C12H12N4O4

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)ethyl alcohol With hydrogenchloride; sodium nitrite In methanol; water at 0℃; for 1h; Stage #2: BARBITURIC ACID With sodium carbonate In methanol; water at 10℃; for 3h;	98.4%

carbon disulfide (75-15-0) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) + methyl iodide (74-88-4) → [4-(2-hydroxy-ethyl)-phenyl]-dithiocarbamic acid methyl ester

Conditions	Yield
With tetra-(n-butyl)ammonium iodide; caesium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 0.25h;	98%

2-(4'-aminophenyl)ethyl alcohol (104-10-9) + Diethyl carbonate (105-58-8) → carbonic acid 2-(4-amino-phenyl)-ethyl ester ethyl ester

Conditions	Yield
With MgLa mixed oxide at 125℃; for 2.5h;	98%

2-(4'-aminophenyl)ethyl alcohol (104-10-9) + Diethyl carbonate (105-58-8) → ethyl 2-(4-amino)phenethyl carbonate

Conditions	Yield
aluminum oxide; cesium fluoride at 129.85℃; for 0.333333h;	98%

2,6-dichloro-4-methylnicotinonitrile (875-35-4) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2,6-bis[4-(2-hydroxyethyl)phenylamino]-3-cyano-4-methylpyridine (631899-53-1)

Conditions	Yield
Stage #1: 2,6-dichloro-4-methylnicotinonitrile; 2-(4'-aminophenyl)ethyl alcohol With sodium carbonate at 120 - 195℃; for 18h; Stage #2: With hydrogenchloride In water	98%

3-(4-dimethylamino-phenyl)-propenal (20432-35-3, 6203-18-5) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 4-[(2E)-3-(4-dimethylaminophenyl)allylideneamino]phenethyl alcohol

Conditions	Yield
In methanol for 1.5h; Reflux;	98%

edaravone (89-25-8) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 4-[4'-(2'-hydroxyethyl)phenylazo]-3-methyl-2-pyrazolin-5-one

Conditions	Yield
Stage #1: 2-(4'-aminophenyl)ethyl alcohol With hydrogenchloride; sodium nitrite In water at 0 - 3℃; for 2h; Stage #2: 3-methyl-1-phenylpyrazolin-5-(4H)-one With sodium hydroxide In water at 0 - 5℃; for 1h;	97.9%

hexakis[μ-(2-propanolato)]hexakis(2-propanolato)tetraaluminum (25443-56-5) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → Al(3+)*2OCH(CH3)2(1-)*OCH2CH2C6H4NH2(1-)=Al(OCH(CH3)2)2(OCH2CH2C6H4NH2)

Conditions	Yield
In benzene to aluminium isopropoxide added p-aminophenyl alcohol (molar ratio 1:1), followed by benzene, contents shaken and refluxed for 18 h; excess benzene removed by pump at room temp.; elem. anal.;	97%

2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-(4-amino-3-bromophenyl)ethan-1-ol (169883-33-4)

Conditions	Yield
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0 - 20℃; for 2h; Inert atmosphere;	96%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 1.5h;	95%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 0℃; for 1h; Inert atmosphere;	91%

2-Chloro-4,6-diamino-1,3,5-triazine (3397-62-4) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-[4-(4,6-diamino-[1,3,5]triazin-2-ylamino)-phenyl]-ethanol (291755-52-7)

Conditions	Yield
With sodium hydroxide Condensation; Heating;	96%
With sodium hydroxide for 3.5h; Heating;

ethyl trifluoroacetate, (383-63-1) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 2-[4-(trifluoroacetylamino)phenyl]ethanol (115166-92-2)

Conditions	Yield
With dmap In tetrahydrofuran for 24h; Heating;	96%

tert-butyldimethylsilyl chloride (18162-48-6) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → 4-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)aniline (173901-21-8)

Conditions	Yield
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h;	96%
Stage #1: 2-(4'-aminophenyl)ethyl alcohol With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyldimethylsilyl chloride In N,N-dimethyl-formamide for 3h;	95%
With dmap; triethylamine In dichloromethane at 20℃; for 12h;	95%

5-chloro-1H-Indole-2-carboxylic acid (10517-21-2) + 2-(4'-aminophenyl)ethyl alcohol (104-10-9) → C17H15ClN2O2 (1036750-28-3)

Conditions	Yield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 20℃; for 14h;	96%

Upstream product

• 100-27-6 2-(4-nitrophenyl)ethanol 
• 60-12-8 2-phenylethanol 
• 6388-74-5 p-Nitrophenyloxirane 
• 5438-70-0 ethyl (4-amino-3,5-dibromophenyl)acetate 
• 5445-26-1 ETHYL 4-NITROPHENYLACETATE 
• 103-45-7 acetic acid phenethyl ester 
• 1081-79-4 β-(2,4-dinitrophenyl)ethyl nitrate 

Downstream Products

• 2133-15-5 Schwefelsaeure-mono-<2-(4-amino-phenyl)-aethylester> 
• 845253-39-6 carbonic acid prop-2-ynyl ester 2-(4-prop-2-ynyloxycarbonylamino-phenyl)-ethyl ester 
• 227467-87-0 ethyl N-[2,6-dibromo-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]aminoacetate 
• 227467-74-5 ethyl N-[2,6-dichloro-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]aminoacetate 
• 227467-80-3 ethyl N-[2,6-dichloro-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxy-phenyl)-1-methylethyl]amino]ethyl]phenyl]-N-methylaminoacetate 
• 1026863-66-0 [Benzyl-(4-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxy-phenyl)-1-methyl-ethylamino]-ethyl}-phenyl)-amino]-acetic acid ethyl ester 
• 227467-88-1 ethyl N-[4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]-2-iodophenyl]aminoacetate 
• 227467-86-9 ethyl N-[2-bromo-4-[2-[[(1S, 2R)-2-hydroxy-2-(4-hydroxyphenyl) methylethyl]amino]ethyl]phenyl]aminoacetate 

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