Conditions | Yield |
---|---|
With sodium tetrahydroborate; Trimethyl borate; dimethyl sulfate In tetrahydrofuran at 20℃; for 1.5h; | 98% |
With sodium tetrahydroborate; iodine In tetrahydrofuran for 2h; Heating; | 88% |
With lithium aluminium tetrahydride In tetrahydrofuran at 67℃; for 2.5h; | 88% |
Conditions | Yield |
---|---|
With β-D-glucose; oxygen for 18h; Reagent/catalyst; Enzymatic reaction; | A n/a B 97.3% |
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With methanol; iodine at 50℃; for 3.5h; | 96% |
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With methanol; iodine at 50℃; for 48h; | 96% |
tert-butyl(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenoxy)dimethylsilane
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With methanol; trimethylsilyl bromide at 20℃; for 5h; chemoselective reaction; | 95% |
With antimonypentachloride; water In acetonitrile at 20℃; for 0.166667h; | 92% |
With iron(III) p-toluenesulfonate hexahydrate In methanol for 26.25h; Reflux; | 84% |
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With methanol; iodine at 50℃; for 10h; | 95% |
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With methanol; iodine at 50℃; for 34h; | 94% |
Methyl 4-hydroxyphenylacetate
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With methanol; Na/SiO2 In tetrahydrofuran at 0 - 25℃; Bouveault-Blanc reduction; Inert atmosphere; | 93% |
With 5 wt% Re/TiO2; hydrogen In octane at 200℃; under 37503.8 Torr; for 24h; Autoclave; chemoselective reaction; | 91% |
With sodium tetrahydroborate In water for 8h; Ambient temperature; | 90% |
4-(2-bromoethyl)phenol
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
Stage #1: 4-(2-bromoethyl)phenol With sodium acetate In water for 3h; Reflux; Stage #2: With sodium hydroxide In water for 0.5h; Inert atmosphere; Reflux; | 88% |
Conditions | Yield |
---|---|
With magnesium In methanol at 20℃; for 10h; | A 83% B n/a |
4-[2-(2-chloroacetyl)oxoethyl]phenyl-2-chloroacetate
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 0 - 20℃; Inert atmosphere; | 81% |
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In ethanol at 20℃; for 1h; | 81% |
A
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
sodium hydrogen sulfate; silica gel In dichloromethane at 20℃; for 1.5h; | A 12% B 76% |
Methyl 4-hydroxyphenylacetate
A
p-hydroxyphenethyl alcohol
B
4-hydroxyphenylacetaldehyde
Conditions | Yield |
---|---|
With diisobutylaluminium hydride In toluene at -78℃; for 5h; | A 10% B 75% |
Conditions | Yield |
---|---|
at 285 - 295℃; for 19h; Inert atmosphere; | 72% |
A
p-hydroxyphenethyl alcohol
B
2-[4'-(tert-butyldiphenylsilyloxy)phenyl]ethanol
Conditions | Yield |
---|---|
With bismuth oxide perchlorate In dichloromethane at 45℃; for 3h; | A n/a B 65% |
2-(3,5-di-t-butyl-4-hydroxyphenyl)ethanol
A
p-cresol
B
benzofuran-5-ol
C
4-Ethylphenol
D
p-hydroxyphenethyl alcohol
E
1-[4-(2-hydroxyethyl)phenoxy]-2-(4'-hydroxyphenyl)ethane
F
di[2-(4-hydroxyphenyl)]ethyl ether
H
6-tert-butyl-5-hydroxybenzofuran
I
phenol
Conditions | Yield |
---|---|
at 295 - 298℃; for 22h; Inert atmosphere; | A n/a B n/a C n/a D 55% E n/a F 40 g G n/a H n/a I n/a |
methanol
A
p-cresol
B
p-hydroxyphenethyl alcohol
C
1-methyl-1-phenylethyl alcohol
D
2-phenylethanol
E
4-tolyl mesylate
Conditions | Yield |
---|---|
With acetone Irradiation; Inert atmosphere; | A n/a B 8% C 8% D 8% E 23% |
Conditions | Yield |
---|---|
With yeast |
Conditions | Yield |
---|---|
With water; silver(l) oxide |
4-(2-chloroethyl)phenol
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With sodium acetate; acetic acid Erwaermen des Reaktionsprodukts mit Natronlauge; |
Conditions | Yield |
---|---|
With yeast |
Conditions | Yield |
---|---|
With yeast | |
Multi-step reaction with 2 steps 1: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 2: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction View Scheme |
Conditions | Yield |
---|---|
With vinegar bacteria | |
Stage #1: L-tyrosine With recombinant parsley (Petroselinum crispum) aromatic acetaldehyde synthese Q06086 at 25℃; for 1h; pH=6.8; aq. phosphate buffer; Enzymatic reaction; Stage #2: With sodium tetrahydroborate In ethanol at 25℃; for 0.0833333h; | |
Multi-step reaction with 3 steps 1: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 2: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction 3: aq. phosphate buffer / 37 °C / Green chemistry; Enzymatic reaction View Scheme |
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
durch gaerende Hefe; | |
bei der Hefegaerung; | |
With lactic acid bacteria | |
Einw. von lebender Hefe bei der alkohol. Vergaerung des Zuckers; | |
Multi-step reaction with 2 steps 1: 270 °C / 12 - 25 Torr 2: yeast View Scheme |
methanol
osmanthuside B
A
p-hydroxyphenethyl alcohol
B
methyl 4-hydroxycinnamate
Conditions | Yield |
---|---|
With acetyl chloride for 0.5h; Heating; |
methanol
fraxiformoside
A
p-hydroxyphenethyl alcohol
B
isoligustroside
Conditions | Yield |
---|---|
for 40h; Heating; | A 13.8 mg B 53.2 mg |
Conditions | Yield |
---|---|
With potassium hydroxide In methanol at 60℃; for 2h; | A n/a B 2 mg |
4-[2-(acetyloxy)ethyl]-4-hydroxy-2,5-cyclohexadien-1-one
A
p-hydroxyphenethyl alcohol
B
rengyol
C
trans-1-(2-hydroxyethyl)cyclohexane-1,4-diol
Conditions | Yield |
---|---|
With sodium tetrahydroborate In methanol Ambient temperature; | A 25 mg B 15 mg C 11 mg |
p-hydroxyphenethyl alcohol
4-(2-bromoethyl)phenol
Conditions | Yield |
---|---|
With PS-triphenylphosphine; bromine In dichloromethane at 0℃; for 1h; | 100% |
With diphenylphosphino-polystyrene; carbon tetrabromide In dichloromethane at 40℃; for 3.5h; | 100% |
With hydrogen bromide In water at 80℃; for 16h; | 100% |
vinyl acetate
p-hydroxyphenethyl alcohol
2-(4-hydroxyphenyl)ethyl acetate
Conditions | Yield |
---|---|
With Candida cylindracea lipase In hexane for 4h; | 100% |
With Candida antartica lipase B In tetrahydrofuran at 20℃; for 4h; Enzymatic reaction; chemoselective reaction; | 100% |
With 1,3-dichlorotetrabutyldistannoxane In tetrahydrofuran at 30℃; for 24h; | 99% |
p-hydroxyphenethyl alcohol
tert-butyldimethylsilyl chloride
tert-butyl(4-(2-(tert-butyldimethylsilyloxy)ethyl)phenoxy)dimethylsilane
Conditions | Yield |
---|---|
With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h; | 100% |
With 1H-imidazole In N,N-dimethyl-formamide Ambient temperature; | 89% |
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide |
p-hydroxyphenethyl alcohol
hydroxytyrosol
Conditions | Yield |
---|---|
With polymer-supported IBX In dimethyl carbonate at 20℃; for 1h; chemoselective reaction; | 100% |
With β-D-glucose; oxygen In aq. phosphate buffer at 37℃; pH=7.0; Enzymatic reaction; | 97.5% |
Stage #1: p-hydroxyphenethyl alcohol at 20℃; for 1h; Stage #2: With sodium dithionite; water for 0.5h; | 90% |
p-hydroxyphenethyl alcohol
epichlorohydrin
1-[4-(2-hydroxyethyl)phenoxy]-2,3-epoxypropane
Conditions | Yield |
---|---|
With potassium carbonate In toluene; acetonitrile | 100% |
With potassium carbonate In butanone for 15h; Heating; | 86% |
Stage #1: p-hydroxyphenethyl alcohol; epichlorohydrin at 80℃; for 1h; Stage #2: With sodium hydroxide at 20℃; | 74% |
p-hydroxyphenethyl alcohol
carbonic acid dimethyl ester
2-(4'-hydroxyphenyl)ethyl methyl carbonate
Conditions | Yield |
---|---|
With sulfuric acid for 7h; Reflux; | 100% |
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 7.5h; | 100% |
With Amberlyst 15 for 12h; Reflux; | 99% |
p-hydroxyphenethyl alcohol
chloroformic acid ethyl ester
carbonic acid ethyl ester 4-(2-hydroxy-ethyl)-phenyl ester
Conditions | Yield |
---|---|
With triethylamine In acetonitrile at -80 - 20℃; Inert atmosphere; | 100% |
With sodium hydroxide In water at -5 - 20℃; for 5h; | 92% |
With sodium hydroxide at -5 - 50℃; for 5h; | 92% |
With sodium hydroxide In water at -5 - 20℃; for 6h; | 83.3% |
p-hydroxyphenethyl alcohol
carbonic acid dimethyl ester
4-methoxyphenethyl methyl carbonate
Conditions | Yield |
---|---|
With 1,8-diazabicyclo[5.4.0]undec-7-ene at 90℃; for 24h; | 100% |
vinyl n-butyrate
p-hydroxyphenethyl alcohol
2-(4-hydroxylphenyl)ethyl butyrate
Conditions | Yield |
---|---|
With Candida antartica lipase B In tetrahydrofuran at 20℃; for 4h; Enzymatic reaction; chemoselective reaction; | 100% |
With Novozym 435 at 40℃; for 1h; Enzymatic reaction; |
p-hydroxyphenethyl alcohol
1-chloro-2-(chloromethyl)benzene
2-(4-(2-chlorobenzyloxy)phenyl)ethanol
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 24h; Reflux; | 100% |
Conditions | Yield |
---|---|
With Candida antarctica at 45℃; for 24h; | 100% |
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction; | 100% |
With lipase from Staphylococcus xylosus immobilized onto CaCO3 for 120h; Enzymatic reaction; | |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Inert atmosphere; |
Conditions | Yield |
---|---|
With Candida antarctica at 45℃; for 24h; | 100% |
With lipase from Staphylococcus xylosus immobilized onto CaCO3 for 120h; Enzymatic reaction; | |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 48h; Inert atmosphere; |
vinyl pivalate
p-hydroxyphenethyl alcohol
4-(2-hydroxyethyl)phenyl pivalate
Conditions | Yield |
---|---|
With rubidium fluoride In acetonitrile at 80℃; for 3h; regiospecific reaction; | 100% |
2,2,2-trifluoroethyl acetate
p-hydroxyphenethyl alcohol
2-(4-hydroxyphenyl)ethyl acetate
Conditions | Yield |
---|---|
With cesium fluoride In acetonitrile at 80℃; for 24h; Reagent/catalyst; | 100% |
p-hydroxyphenethyl alcohol
butyric acid
2-(4-hydroxylphenyl)ethyl butyrate
Conditions | Yield |
---|---|
With Candida antarctica at 45℃; for 24h; | 100% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 24h; |
Conditions | Yield |
---|---|
With Candida antarctica at 45℃; for 24h; | 100% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction; | 100% |
p-hydroxyphenethyl alcohol
2-Pentanone
2-(4-hydroxylphenyl)ethyl butyrate
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction; | 100% |
Conditions | Yield |
---|---|
With Candida antarctica lipase B at 45℃; for 24h; Enzymatic reaction; | 100% |
Conditions | Yield |
---|---|
With potassium carbonate In acetone for 18h; Heating; | 99.3% |
With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; Inert atmosphere; | 98% |
With potassium carbonate In acetone Reflux; | 98% |
p-hydroxyphenethyl alcohol
acetic anhydride
2-(4-acetoxyphenyl)ethyl acetate
Conditions | Yield |
---|---|
With pyridine at 20℃; for 24h; Inert atmosphere; | 99% |
cerium triflate In acetonitrile at 20℃; for 0.2h; | 98% |
With tributylphosphine at 30℃; for 4h; other reagents: Sc(OTf)3, 4-(dimethylamino)pyridine/pyridine; | 95% |
p-hydroxyphenethyl alcohol
benzyl chloride
2-(4-benzyloxyphenyl)ethanol
Conditions | Yield |
---|---|
With potassium carbonate In N,N-dimethyl-formamide at 65℃; for 24h; | 99% |
Stage #1: p-hydroxyphenethyl alcohol With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: benzyl chloride With tetra-(n-butyl)ammonium iodide at 20℃; for 18h; | 88% |
In ethanol for 9h; Heating; |
p-hydroxyphenethyl alcohol
methyl 2-oxocyclopentane-1-carboxylate
Conditions | Yield |
---|---|
With N,N-3-diethylaminopropylated silica gel In xylene for 3h; Heating; | 99% |
p-hydroxyphenethyl alcohol
4-(2-Hydroxyethyl)cyclohexanol
Conditions | Yield |
---|---|
With borax; hydrogen; palladium 10% on activated carbon In isopropyl alcohol at 80℃; under 7500.75 Torr; for 22h; | 99% |
p-hydroxyphenethyl alcohol
Conditions | Yield |
---|---|
With 1,4-diaza-bicyclo[2.2.2]octane In dichloromethane at 20℃; for 16h; | 99% |
Conditions | Yield |
---|---|
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 70℃; for 16h; | 99% |
With chloro-trimethyl-silane; sodium iodide In acetonitrile at 70℃; for 24h; Inert atmosphere; | 95% |
With 1H-imidazole; iodine; triphenylphosphine In diethyl ether; acetonitrile at 20℃; for 4h; | 91% |
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0 - 20℃; Inert atmosphere; | 70% |
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 20℃; for 4h; |
Conditions | Yield |
---|---|
Stage #1: p-hydroxyphenethyl alcohol With sodium hydride In tetrahydrofuran at 20℃; for 0.5h; Stage #2: p-nitrophenyl isothiocyanate In tetrahydrofuran at 20℃; for 18h; Further stages.; | 99% |
Conditions | Yield |
---|---|
With (μ-oxo)bis[(1,2-ethanediamino-N,N'-bis(salicylidene))iron(III)] In 5,5-dimethyl-1,3-cyclohexadiene at 140℃; for 24h; Inert atmosphere; Schlenk technique; chemoselective reaction; | 99% |
p-hydroxyphenethyl alcohol
ethyl acetate
2-(4-hydroxyphenyl)ethyl acetate
Conditions | Yield |
---|---|
With sodium hydrogen sulfate In hexane for 26h; Heating; | 98% |
With sodium hydrogen sulfate; silica gel In hexane Heating; | 98% |
With toluene-4-sulfonic acid at 80℃; for 5h; Reagent/catalyst; Temperature; | 98.9% |
p-hydroxyphenethyl alcohol
perfluoro(4-methyl-3-isopropyl-2-pentene)
Conditions | Yield |
---|---|
With potassium carbonate In tetrahydrofuran for 4h; Inert atmosphere; Reflux; | 98.6% |
Molecule structure of 4-Hydroxyphenethyl alcohol (CAS NO.501-94-0):
IUPAC Name: 4-(2-Hydroxyethyl)phenol
Molecular Weight: 138.1638 g/mol
Molecular Formula: C8H10O2
Density: 1.168 g/cm3
Melting Point: 89-92 °C(lit.)
Boiling Point: 287.8 °C at 760 mmHg
Flash Point: 143.2 °C
Index of Refraction: 1.577
Molar Refractivity: 39.21 cm3
Molar Volume: 118.1 cm3
Surface Tension: 50.8 dyne/cm
Enthalpy of Vaporization: 55.66 kJ/mol
Vapour Pressure: 0.00113 mmHg at 25 °C
Water Solubility: slightly soluble
XLogP3: 0.4
H-Bond Donor: 2
H-Bond Acceptor: 2
Rotatable Bond Count: 2
Tautomer Count: 2
Exact Mass: 138.06808
MonoIsotopic Mass: 138.06808
Topological Polar Surface Area: 40.5
Heavy Atom Count: 10
Canonical SMILES: C1=CC(=CC=C1CCO)O
InChI: InChI=1S/C8H10O2/c9-6-5-7-1-3-8(10)4-2-7/h1-4,9-10H,5-6H2
InChIKey: YCCILVSKPBXVIP-UHFFFAOYSA-N
EINECS: 207-930-8
Product Categories: Alcohols and Derivatives; Benzhydrols, Benzyl & Special Alcohols; Benzene derivates; Alkohols; API intermediates
4-Hydroxyphenethyl alcohol (CAS NO.501-94-0) is used as pharmaceutical intermediates.
Hazard Codes: Xi
Risk Statements: 36/37/38
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements: 26-37/39-24/25-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37/39:Wear suitable gloves and eye/face protection.
S24/25:Avoid contact with skin and eyes.
S36:Wear suitable protective clothing.
WGK Germany: 3
F: 10
Hazard Note: Irritant
HS Code: 29072900
4-Hydroxyphenethyl alcohol (CAS NO.501-94-0) is also named as 2-(4-Hydroxyphenyl)ethanol ; NSC 59876 ; p-Hydroxyphenethyl alcohol ; 4-Hydroxyphenethyl alcohol ; Benzeneethanol, 4-hydroxy- . 4-Hydroxyphenethyl alcohol (CAS NO.501-94-0) is off-white to light beige crystals or crystalline.
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