Conditions | Yield |
---|---|
With magnesium chloride In isopropyl alcohol at 25℃; pH=7; Catalytic behavior; | 100% |
With isopropyl alcohol; 1-butyl-3-methylimidazolium trifluoromethanesulfonimide at 40℃; pH=6; Microbiological reaction; | 95% |
With ketoreductase P2-H07; isopropyl alcohol; NADPH In aq. phosphate buffer at 30℃; for 24h; pH=7; Reagent/catalyst; Enzymatic reaction; stereoselective reaction; | 93% |
Conditions | Yield |
---|---|
Stage #1: bromobenzene With magnesium In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: With copper(l) cyanide In tetrahydrofuran at -35℃; for 0.5h; Stage #3: (R)-propylene oxide In tetrahydrofuran at -35 - 20℃; for 1.5h; | 98% |
With pyridine; 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; 4,4'-bipyridine; NiI2*3.9H2O; triethylamine hydrochloride; sodium iodide; zinc at 20℃; for 12h; | 86% |
(+)-(R,R)-β-methylstyrene oxide
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
Stage #1: (+)-(R,R)-β-methylstyrene oxide With C30H32FeNPS at 20℃; for 5h; Stage #2: With hydrogenchloride In methanol for 1h; Reflux; | 93% |
With hydrogen; Pd/magnetite In ethyl acetate at 23℃; under 760.051 Torr; for 0.7h; | |
Multi-step reaction with 2 steps 1: aq. K2CO3 / Heating 2: (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl View Scheme |
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With methanol; potassium carbonate for 16h; Reflux; Inert atmosphere; | 93% |
Conditions | Yield |
---|---|
With triisopropoxytitanium(IV) chloride; (Ra)-2'-[(S)-hydroxy(pyridin-4-yl)methyl]-(1,1'-binaphthalen)-2-ol In diethyl ether; hexane at -20℃; for 0.166667h; enantioselective reaction; | 93% |
Conditions | Yield |
---|---|
With air; cells of Geotrichum candidum IFO 5767 In water at 30℃; for 24h; | 80% |
(R)-1-(2-Phenyl-[1,3]dithian-2-yl)-ethanol
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With ethanol; nickel at 50℃; or nBu3SnH, AIBN, toluene, reflux; | 80% |
methyllithium
phenylacetaldehyde
A
(S)-1-phenylpropan-2-ol
B
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With triisopropoxytitanium(IV) chloride; (Sa)-2'-((S)-hydroxy(phenyl)methyl)-[1,1'-binaphthalen]-2-ol In diethyl ether; hexane at -20℃; for 0.166667h; enantioselective reaction; | A n/a B 80% |
Stage #1: methyllithium; phenylacetaldehyde With (Sa)-2'-[(R)-hydroxy(phenyl)methyl]-(1,1'-binaphthalen)-2-ol; titanium(IV)isopropoxide In toluene at -40℃; for 1h; Inert atmosphere; Stage #2: With hydrogenchloride In water Inert atmosphere; optical yield given as %ee; enantioselective reaction; |
Conditions | Yield |
---|---|
With methanesulfonic acid; (R,R)-dihydroborate In hexane at -20℃; for 48h; Title compound not separated from byproducts; | A n/a B 69% |
With nicotinamide adenine dinucleotide; rat liver homogenate supernatant at 37℃; Product distribution; other catalysts; | |
With lithium aluminium tetrahydride; crowned 2,2'-dihydroxy-1,1'-binaphthyl (S,S)-4 In tetrahydrofuran at 0℃; for 24h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
3-phenyl-2-propanol
A
(S)-1-phenylpropan-2-ol
B
(R)-1-phenyl-propan-2-ol
C
1-phenyl-acetone
Conditions | Yield |
---|---|
With (1R)-N-oxyl-1-(N-benzylcarbamoyl)-8-azabicyclo[3.2.1]octane; sodium hydrogencarbonate; sodium bromide In dichloromethane; water at 0℃; Electrochemical reaction; optical yield given as %ee; enantioselective reaction; | A n/a B n/a C 66% |
With Sphingomonas paucimobilis NCIMB 8195 In water; N,N-dimethyl-formamide for 120h; | A n/a B n/a C 40% |
With Geotrichum candidum IFO 4597 cells on BL-100 polymer; cyclohexanone In hexane at 30℃; for 24h; Oxidation; | A n/a B n/a C 44 % Chromat. |
Conditions | Yield |
---|---|
With phosphate buffer; lipase at 20℃; | 47% |
With sodium hydroxide; dm-3 phosphate buffer at 25℃; lipoprotein lipase from Pseudomonas aeruginosa (LPL Amano 1), pH 6.9-7.0; |
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With phosphate buffer; lipase at 20℃; | 45% |
4-((1-methyl-2-phenylethoxy)carbonyl)butanoic acid
A
C14H18O4
C
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With lipase from candida antartica In aq. phosphate buffer at 30℃; for 48h; | A n/a B n/a C 39% |
bromobenzene
(R)-propylene oxide
A
(S)-2-phenyl-1-propanol
B
(+)-(R)-2-phenylpropanol
C
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; manganese; (1,2-dimethoxyethane)dichloronickel(II); bis(η5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride; sodium thiophenolate; triethylamine hydrochloride In benzene at 20℃; for 4h; Inert atmosphere; Glovebox; Autoclave; enantioselective reaction; | A n/a B n/a C 30% |
3-((1-methyl-2-phenylethoxy)carbonyl)propanoic acid
A
C13H16O4
B
C13H16O4
C
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With lipase from candida antartica In aq. phosphate buffer at 30℃; for 48h; | A n/a B n/a C 22% |
bromobenzene
methyloxirane
A
(S)-2-phenyl-1-propanol
B
(+)-(R)-2-phenylpropanol
C
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; manganese; (1,2-dimethoxyethane)dichloronickel(II); bis(η5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride; triethylamine hydrochloride In benzene at 20℃; for 12h; Inert atmosphere; Glovebox; Autoclave; enantioselective reaction; | A n/a B n/a C 16% |
bromobenzene
methyloxirane
A
(S)-2-phenyl-1-propanol
B
(S)-1-phenylpropan-2-ol
C
(+)-(R)-2-phenylpropanol
D
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; manganese; (1,2-dimethoxyethane)dichloronickel(II); bis(η5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride; triethylamine hydrochloride In benzene at 20℃; for 12h; Inert atmosphere; Glovebox; Autoclave; enantioselective reaction; | A n/a B n/a C 11% D 3% |
bromobenzene
methyloxirane
A
(S)-2-phenyl-1-propanol
B
(+)-(R)-2-phenylpropanol
C
(R)-1-phenyl-propan-2-ol
D
(S)-(+)-(2-hydroxy-1-propyl)-phenyl thioether
E
(R)-2-hydroxypropane-1-phenylsulfide
Conditions | Yield |
---|---|
With [2,2]bipyridinyl; manganese; (1,2-dimethoxyethane)dichloronickel(II); bis(η5((1R,2S,5R)-5-methyl-2-[prop-2-yl]-cyclohex-1-yl)cyclopentadienyl)-titanium dichloride; sodium thiophenolate; triethylamine hydrochloride at 20℃; for 2.5h; Inert atmosphere; Glovebox; Autoclave; enantioselective reaction; | A n/a B n/a C 9% D n/a E n/a |
3-phenyl-2-propanol
A
(S)-1-phenylpropan-2-ol
B
(R)-1-phenyl-2-acetoxypropane
C
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
Yield given. Yields of byproduct given. Title compound not separated from byproducts; |
1-phenylpropan-2-yl acetate
A
(S)-1-phenylpropan-2-ol
B
(R)-1-phenyl-2-acetoxypropane
C
(R)-1-phenyl-propan-2-ol
D
(S)-1-phenyl-propan-2-ol acetate
Conditions | Yield |
---|---|
With water at 30℃; for 168h; Product distribution; asymmetric hydrolysis and resolution by Pseudomonas cepacia; | |
With recombinant pig liver esterase In phosphate buffer for 2h; pH=7.5; Enzymatic reaction; |
(R)-1-phenyl-2-acetoxypropane
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With sodium hydroxide at 25℃; for 4h; | |
With lithium hydroxide In methanol at 20℃; for 3h; | |
With sodium hydroxide In methanol; water | |
With potassium hydroxide In tetrahydrofuran; methanol for 12h; | |
With water; potassium hydroxide In methanol | n/a |
(2S)-2-phenyl-1-propanamine
A
1-methyl-1-phenylethyl alcohol
B
1-Phenyl-1-propanol
C
(RS)-2-phenyl-1-propanol
D
(S)-1-phenylpropan-2-ol
E
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With sodium nitrite In perchloric acid; water Product distribution; Mechanism; |
rac-1-phenyl-2-propyl-propionate
A
(S)-1-phenylpropan-2-ol
B
propionic acid-((S)-1-methyl-2-phenyl-ethyl ester)
C
(R)-1-phenyl-propan-2-ol
D
Propionic acid (R)-1-methyl-2-phenyl-ethyl ester
Conditions | Yield |
---|---|
With water at 30℃; for 168h; Product distribution; asymmetric hydrolysis and resolution by Pseudomonas cepacia; |
(1R,2S,SR)-1-methyl-2-(methylsulfinyl)phenethyl alcohol
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With nickel In tetrahydrofuran for 2h; Ambient temperature; |
Propionic acid (R)-1-methyl-2-phenyl-ethyl ester
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With sodium hydroxide at 25℃; for 4h; | |
With sodium hydroxide In methanol; water |
((R)-1-Methyl-2-phenyl-ethoxy)-diphenyl-silane
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With hydrogen cation In water Yield given; |
Conditions | Yield |
---|---|
for 24h; Lactobacillus kefir; Yield given; |
(1S,2R)-1-phenylpropane-1,2-diol
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
(i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl; Multistep reaction; |
3-phenyl-2-propanol
benzoyl chloride
A
(S)-1-phenylpropan-2-ol
B
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With 4 A molecular sieve; chiral diamine; triethylamine In dichloromethane at -78℃; for 3h; Yield given; Yields of byproduct given; |
(R)-1-phenyl-propan-2-ol
p-toluenesulfonyl chloride
(R)-1-phenylpropan-2-yl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; Inert atmosphere; | 99% |
With pyridine In dichloromethane at 20℃; for 48h; | 90% |
With pyridine; dmap at 30℃; for 3h; |
(R)-1-phenyl-propan-2-ol
methyl 3-hydroxy-5-isopropoxybenzoate
methyl 3-isopropoxy-5-[(1S)-1-methyl-2-phenylethoxy]benzoate
Conditions | Yield |
---|---|
Stage #1: (R)-1-phenyl-propan-2-ol; methyl 3-hydroxy-5-isopropoxybenzoate With triphenylphosphine In dichloromethane at 0℃; for 0.5h; Stage #2: With di-isopropyl azodicarboxylate In dichloromethane at 0 - 20℃; Stage #3: (R)-1-phenyl-propan-2-ol With di-isopropyl azodicarboxylate; triphenylphosphine at 0 - 20℃; for 2.83333h; | 97% |
Conditions | Yield |
---|---|
With C10H10Zr(2+)*2CF3O3S(1-)*C4H8O at 80℃; for 24h; Sealed tube; | 93% |
(R)-1-phenyl-propan-2-ol
methanesulfonyl chloride
(R)-1-phenylpropanyl-2-yl methansulfonate
Conditions | Yield |
---|---|
With triethylamine In dichloromethane at 0℃; for 1h; | 92% |
With pyridine at -15 - 20℃; for 2h; | 87% |
With triethylamine In dichloromethane at 20℃; Inert atmosphere; |
(R)-1-phenyl-propan-2-ol
(R)-1-phenylpropan-2-yl 4-methylbenzenesulfonate
Conditions | Yield |
---|---|
With pyridine; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 100h; | 90% |
(R)-1-phenyl-propan-2-ol
(+)-2-chloro-1-phenylpropane
Conditions | Yield |
---|---|
With pyridine; bis(trichloromethyl) carbonate In dichloromethane at 0℃; Reflux; | 89% |
3-hydroxy-5-((S)-2-methoxy-1-methyl-ethoxy)-benzoic acid methyl ester
(R)-1-phenyl-propan-2-ol
3-((S)-2-methoxy-1-methyl-ethoxy)-5-((S)-1-methyl-2-phenyl-ethoxy)-benzoic acid methyl ester
Conditions | Yield |
---|---|
Stage #1: 3-hydroxy-5-((S)-2-methoxy-1-methyl-ethoxy)-benzoic acid methyl ester; (R)-1-phenyl-propan-2-ol With triphenylphosphine In tetrahydrofuran at 0℃; for 0.0833333h; Stage #2: With di-isopropyl azodicarboxylate In tetrahydrofuran at 20℃; for 12h; | 81% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 12.0833h; | 81% |
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 16h; | 80% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran; toluene at 0 - 20℃; |
Conditions | Yield |
---|---|
Stage #1: (R)-1-phenyl-propan-2-ol With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.5h; Stage #2: bis(diethylamino)chlorophosphine In tetrahydrofuran; hexane at -70 - 20℃; | 80% |
(R)-1-phenyl-propan-2-ol
(S)-2-bromo-1-phenylpropane
Conditions | Yield |
---|---|
With 1H-imidazole; bromine; triphenylphosphine In dichloromethane at 0 - 20℃; | 68% |
With carbon tetrabromide; triphenylphosphine |
(R)-1-phenyl-propan-2-ol
triethylamine
A
(-)-(R)-1-phenylpropan-2-yl diethylcarbamate
B
(+)-2-chloro-1-phenylpropane
Conditions | Yield |
---|---|
With bis(trichloromethyl) carbonate In dichloromethane at 0 - 20℃; Solvent; Concentration; | A 27% B 45% |
4,5-dicyano-1H-imidazole
(R)-1-phenyl-propan-2-ol
(S)-(+)-1-(1-Phenyl-2-propyl)imidazole-4,5-dicarbonitrile
Conditions | Yield |
---|---|
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 0℃; for 0.5h; | 39% |
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran for 0.5h; Ambient temperature; | 39% |
(R)-1-phenyl-propan-2-ol
Conditions | Yield |
---|---|
With triphenylphosphine, polymer bound In 1,2-dimethoxyethane at 20℃; | 13% |
Molecular Structure of (R)-1-Phenyl-2-propanol (1572-95-8):
Systematic Name: (2S)-1-Phenylpropan-2-ol
Molecular Formula: C9H12O
Molecular Weight: 136.191
H bond acceptors: 1
H bond donors: 1
Freely Rotating Bonds: 3
Index of Refraction: 1.525
Molar Refractivity: 41.92 cm3
Molar Volume: 136.6 cm3
Surface Tension: 37.3 dyne/cm
Density: 0.996 g/cm3
Flash Point: 85 °C
Boiling Point: 220 °C at 760 mmHg
Enthalpy of Vaporization: 48.24 kJ/mol
Vapour Pressure: 0.067 mmHg at 25 °C
Water Solubility: 5838 mg/L at 25 °C
Refractive Index: n20/D 1.521
Safety Information of (R)-1-Phenyl-2-propanol (1572-95-8):
Hazard Codes: Xi
Hazard Note: Irritant
Safety Statements: 23-24/25
23: Do not breathe gas/fumes/vapor/spray (appropriate wording to be specified by the manufacturer)
24/25: Avoid contact with skin and eyes
WGK Germany: 3
(R)-1-Phenyl-2-propanol (1572-95-8) is also known as R(-)-1-Phenyl-2-propanol ; R(-)-alpha-Methylphenethyl alcohol ; (2R)-1-Phenyl-2-propanol ; (R)-1-Phenylpropan-2-ol ; (R)-α-Methylbenzeneethanol . It is often used in organic synthesis.
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