(S)-1-Phenyl-2-propanol supplier

Name
S(+)-1-PHENYL-2-PROPANOL
EINECS
CAS No. 1517-68-6
Article Data144
CAS DataBase
Density 0.996 g/cm³
Solubility
Melting Point
Formula C₉H₁₂O
Boiling Point 220 °C at 760 mmHg
Molecular Weight 136.194
Flash Point 85 °C
Transport Information
Appearance
Safety 23-24/25
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms Benzeneethanol,a-methyl-, (S)-;(+)-(S)-1-Phenyl-2-propanol;Phenethylalcohol, a-methyl-, (S)-(+)- (8CI);(S)-(+)-Benzylmethylcarbinol;(S)-1-Phenyl-2-propanol;(+)-1-Phenyl-2-propanol;(+)-a-Methylbenzeneethanol;(+)-a-Methylphenethyl alcohol;(S)-(+)-1-Phenyl-2-propanol;
PSA 20.23000
LogP 1.60990

Synthetic route

: 103-79-7
1-phenyl-acetone

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus W110I mutant; nicotinamide adenine dinucleotide phosphate In isopropyl alcohol at 50℃; for 6h; pH=8; Reagent/catalyst; Enzymatic reaction; enantioselective reaction;	100%
With Kluyveromyces marxianus CBS 6556 In ethanol at 30℃; for 96h; Microbiological reaction; Yeast maintenance medium; Enzymatic reaction; optical yield given as %ee; enantioselective reaction;	98%
With Tween 80; bakers' yeast; Sucrose at 25 - 32℃;	90%

: 108-86-1
bromobenzene

: 16088-62-3
(S)-Propylene oxide

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

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: (S)-Propylene oxide In tetrahydrofuran at -35 - 20℃; for 1.5h;	98%
Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.333333h; Stage #2: (S)-Propylene oxide In tetrahydrofuran; hexane at -50 - 20℃; for 1.83333h;	71%

: (S)-1-[4-(1-Phenyl-1H-tetrazol-5-yl)-phenyl]-propan-2-ol

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol for 48h;	95%

: 61393-94-0
(R)-2-benzyloxirane

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Heating;	92%
With lithium aluminium tetrahydride In diethyl ether for 2h; Heating;	86%
With sodium tetrahydroborate In ethanol for 2h; Reflux; regioselective reaction;	81%

: 4518-66-5
(1S,2S)-(-)-1-phenyl-1-propene oxide

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With formic acid; triethylamine; Pd0-EnCatTM In ethyl acetate at 23℃; for 3h;	90%
Multi-step reaction with 2 steps 1: aq. K2CO3 / Heating 2: (i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl View Scheme

: 917-54-4
methyllithium

: 122-78-1
phenylacetaldehyde

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 1572-95-8
(R)-1-phenyl-propan-2-ol

Conditions

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;

...Expand

: 100-58-3
phenylmagnesium bromide

: 16088-62-3
(S)-Propylene oxide

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
Stage #1: phenylmagnesium bromide With copper(l) cyanide In diethyl ether at -35℃; for 0.5h; Stage #2: (S)-Propylene oxide In diethyl ether at -35 - 20℃; for 1.5h;	74%

: 873-66-5
1-propenylbenzene

: 74-88-4
methyl iodide

A: 74365-65-4
(2S,3S)-(-)-erythro-3-phenyl-2-butanol

B: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
Stage #1: 1-propenylbenzene; methyl iodide With (R,R)-(−)-2,3-bis(t-butylmethylphosphino)quinoxaline; potassium methanolate; bis(pinacol)diborane; copper(l) chloride In tetrahydrofuran at 25℃; for 12h; Glovebox; Stage #2: With sodium peroxoborate tetrahydrate In tetrahydrofuran; water at 0 - 25℃; for 6h; Solvent; Glovebox; enantioselective reaction;	A 70% B n/a

...Expand

: 103-79-7
1-phenyl-acetone

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 1572-95-8
(R)-1-phenyl-propan-2-ol

Conditions

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;

: [2S,(S)S]-1-[2-(p-tolylsulfinyl)phenyl]propan-2-ol

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With tert.-butyl lithium In tetrahydrofuran at -78℃; for 0.166667h;	67%

: 698-87-3
3-phenyl-2-propanol

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 1572-95-8
(R)-1-phenyl-propan-2-ol

C: 103-79-7
1-phenyl-acetone

Conditions

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.

...Expand

: 698-87-3
3-phenyl-2-propanol

: 876-27-7
4-chlorophenyl acetate

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 2114-33-2, 29393-15-5, 115630-98-3, 116907-36-9
(R)-1-phenyl-2-acetoxypropane

Conditions

Conditions	Yield
With (η5-indenyl)ruthenium(bis(triphenylphosphine))chloride; Pseudomonas cepocia lipase; triethylamine at 60℃; for 43h; Esterification; resolution of racemate; Enzymatic reaction; Title compound not separated from byproducts;	A n/a B 60%

...Expand

: 116386-53-9
(-)-(RS,R)-1-chloro-2-phenylethyl p-tolyl sulfoxide

: 66423-62-9
2,5,5-trimethyl-1,3,2-dioxaborinane

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
Stage #1: (-)-(RS,R)-1-chloro-2-phenylethyl p-tolyl sulfoxide With ethylmagnesium chloride In tetrahydrofuran; toluene at -78℃; for 0.8h; Stage #2: 2,5,5-trimethyl-1,3,2-dioxaborinane In tetrahydrofuran; toluene Heating; Stage #3: With sodium hydroxide; dihydrogen peroxide In various solvents at 0 - 20℃; for 3h;	56%

: 698-87-3
3-phenyl-2-propanol

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 103-79-7
1-phenyl-acetone

Conditions

Conditions	Yield
With Arthrobacter atrocyaneus In N,N-dimethyl-formamide at 32℃; for 72h; Microbiological reaction; enantioselective reaction;	A 52% B n/a

: 108-05-4
vinyl acetate

: 698-87-3
3-phenyl-2-propanol

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 2114-33-2, 29393-15-5, 115630-98-3, 116907-36-9
(R)-1-phenyl-2-acetoxypropane

Conditions

Conditions	Yield
With Candida antarctica lipase B In 1,1,1,2-tetrafluoroethane at 25℃; for 72h; Resolution of racemate; Enzymatic reaction; optical yield given as %ee;	A n/a B 47%
With 4 A molecular sieve In hexane at 25℃; for 5.5h; lipase from Pseudomonas sp.;	A 43% B 46%
With Burkholderia cepacia lipase immobilized on ceramic particles In tetrahydrofuran at 20℃; for 48h;
With Pseudomonas cepacia lipase In di-isopropyl ether at 20℃; for 4h;	A n/a B 281 mg

...Expand

: 698-87-3
3-phenyl-2-propanol

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
	43%

: 698-87-3
3-phenyl-2-propanol

: 123-62-6
propionic acid anhydride

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 116809-20-2
Propionic acid (R)-1-methyl-2-phenyl-ethyl ester

Conditions

Conditions	Yield
In benzene at 21℃; for 10h; lipase Amano P/Celite 577; Yields of byproduct given;	A n/a B 39%

...Expand

: 108-86-1
bromobenzene

: 75-56-9, 16033-71-9
methyloxirane

A: 37778-99-7
(S)-2-phenyl-1-propanol

B: 1517-68-6
(S)-1-phenylpropan-2-ol

C: 1123-85-9, 37778-99-7, 98103-87-8, 19141-40-3
(+)-(R)-2-phenylpropanol

D: 1572-95-8
(R)-1-phenyl-propan-2-ol

Conditions

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%

...Expand

: 698-87-3
3-phenyl-2-propanol

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 2114-33-2, 29393-15-5, 115630-98-3, 116907-36-9
(R)-1-phenyl-2-acetoxypropane

C: 1572-95-8
(R)-1-phenyl-propan-2-ol

Conditions

Conditions	Yield
Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 2114-33-2
1-phenylpropan-2-yl acetate

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 2114-33-2, 29393-15-5, 115630-98-3, 116907-36-9
(R)-1-phenyl-2-acetoxypropane

C: 1572-95-8
(R)-1-phenyl-propan-2-ol

D: 29393-15-5
(S)-1-phenyl-propan-2-ol acetate

Conditions

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;

...Expand

: 17596-79-1
(2S)-2-phenyl-1-propanamine

A: 617-94-7
1-methyl-1-phenylethyl alcohol

B: 93-54-9
1-Phenyl-1-propanol

C: 1123-85-9
(RS)-2-phenyl-1-propanol

D: 1517-68-6
(S)-1-phenylpropan-2-ol

E: 1572-95-8
(R)-1-phenyl-propan-2-ol

Conditions

Conditions	Yield
With sodium nitrite In perchloric acid; water Product distribution; Mechanism;

...Expand

: 157752-41-5
rac-1-phenyl-2-propyl-propionate

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 116809-20-2
propionic acid-((S)-1-methyl-2-phenyl-ethyl ester)

C: 1572-95-8
(R)-1-phenyl-propan-2-ol

D: 116809-20-2
Propionic acid (R)-1-methyl-2-phenyl-ethyl ester

Conditions

Conditions	Yield
With water at 30℃; for 168h; Product distribution; asymmetric hydrolysis and resolution by Pseudomonas cepacia;

...Expand

: 698-87-3
3-phenyl-2-propanol

: 108-24-7
acetic anhydride

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 2114-33-2, 29393-15-5, 115630-98-3, 116907-36-9
(R)-1-phenyl-2-acetoxypropane

C: 29393-15-5
(S)-1-phenyl-propan-2-ol acetate

Conditions

Conditions	Yield
In benzene at 21℃; for 30h; lipase Amano P/Celite 577; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

...Expand

: 90472-62-1
((S)-1-Methyl-2-phenyl-ethoxy)-diphenyl-silane

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With hydrogen cation In water Yield given;

: 4773-35-7
1-chloro-1-phenylpropan-2-one

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: 160332-15-0
(+)-(1S,2S)-1-phenyl-1-chloro-2-propanol

C: 160332-16-1
(+)-(1R,2S)-1-phenyl-1-chloro-2-propanol

Conditions

Conditions	Yield
for 24h; Bakers' yeast; Yield given. Yields of byproduct given;

...Expand

: 29393-15-5
(S)-1-phenyl-propan-2-ol acetate

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With potassium carbonate In methanol Ambient temperature;

: Chloro-acetic acid (S)-1-methyl-2-phenyl-ethyl ester

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
With potassium carbonate In methanol Ambient temperature;

: Pyridin-4-yl-acetic acid 1-methyl-2-phenyl-ethyl ester

A: 28356-58-3
pyridine-4-acetic acid

B: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
In methanol; water Rate constant; penicillin G acylase in pH 8 phosphate buffer;

: 40421-52-1
(1R,2S)-1-phenylpropane-1,2-diol

: 1517-68-6
(S)-1-phenylpropan-2-ol

Conditions

Conditions	Yield
(i) PBr5, CHCl3, (ii) Zn-Cu, aq. HCl; Multistep reaction;

: 5770-05-8
[18O]-methanol

: 37778-99-7
(S)-2-phenyl-1-propanol

A: 1517-68-6
(S)-1-phenylpropan-2-ol

B: <18O>-2-phenyl-2-methoxypropane

C: <18O>-1-phenyl-1-methoxypropane

D: <18O>-(S)-1-phenyl-2-methoxypropane

Conditions

Conditions	Yield
With methane; oxygen In gaseous matrix at 25℃; Product distribution; Kinetics; Mechanism; Irradiation; other temperatures;

...Expand

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 98-59-9
p-toluenesulfonyl chloride

: 53334-59-1
(S)-1-phenylpropan-2-yl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With trimethylamine hydrochloride; triethylamine In dichloromethane at 0℃; Inert atmosphere;	98%
With pyridine; dmap at 0 - 20℃; for 5.5h;	88%
With pyridine In dichloromethane at 20℃; for 48h;	88%
With pyridine; dmap at 30℃; for 3h;	85%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 7-fluorophenazin-2-ol

: (R)-2-fluoro-7-((1-phenylpropan-2-yl)oxy)phenazine

Conditions

Conditions	Yield
With diisopropyl (E)-azodicarboxylate; triphenylphosphine In tetrahydrofuran at 0 - 20℃; for 24h; Inert atmosphere;	92%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 124-63-0
methanesulfonyl chloride

: (S)-1-phenylpropan-2-yl methanesulfonate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 1h;	91%
With triethylamine In dichloromethane at 0 - 20℃;	85%
With triethylamine In dichloromethane at 0℃; for 0.5h;

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 140145-83-1
(+)(S)-1-cyclohexyl-propanol-(2)

Conditions

Conditions	Yield
With hydrogen; Aliquat 336; rhodium(III) chloride	90%
With acetic acid; platinum Hydrogenation;

: 20445-31-2
R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid

: 1517-68-6
(S)-1-phenylpropan-2-ol

: C9H11OC10H8O2F3

Conditions

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 13h;	87%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 63798-14-1
(-)-(R)-(2-bromopropyl)benzene

Conditions

Conditions	Yield
With 1H-imidazole; bromine; triphenylphosphine In dichloromethane at 0 - 20℃;	80%
With triphenylphosphine; lithium bromide; diethylazodicarboxylate at 20℃; for 24h;	32%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 53334-59-1
(S)-1-phenylpropan-2-yl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
With pyridine; p-toluenesulfonyl chloride In dichloromethane at 20℃; for 100h;	78%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 55449-46-2
(-)-2-chloro-1-phenylpropane

Conditions

Conditions	Yield
With pyridine; thionyl chloride In chloroform at 0 - 60℃; for 2.5h;	74%
With pyridine; thionyl chloride at 65℃; for 6h;	29%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 107-30-2
chloromethyl methyl ether

: (+)-(3S)-3-methyl-3,4-dihydro-1H-isochromene

Conditions

Conditions	Yield
With zinc(II) chloride at 20℃; for 0.5h;	74%

: 685-83-6
bis(diethylamino)chlorophosphine

: 1517-68-6
(S)-1-phenylpropan-2-ol

: (R)-N,N,N',N'-tetraethyl-1-(1-phenylpropan-2-yloxy)phosphinediamine

Conditions

Conditions	Yield
Stage #1: (S)-1-phenylpropan-2-ol With n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.5h; Stage #2: bis(diethylamino)chlorophosphine In tetrahydrofuran; hexane at -70 - 20℃;	71%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 10304-81-1, 55449-46-2, 116698-42-1, 16583-73-6
(+)-2-chloro-1-phenylpropane

Conditions

Conditions	Yield
With thionyl chloride at 20 - 30℃; for 26h;	65%

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 767-00-0
4-cyanophenol

: (R)-4-((1-phenylpropan-2-yl)oxy)benzonitrile

Conditions

Conditions	Yield
With di-isopropyl azodicarboxylate; triphenylphosphine In 2-methyltetrahydrofuran at 20℃; for 3h; Mitsunobu Displacement;	51%

: 32315-10-9
bis(trichloromethyl) carbonate

: 1517-68-6
(S)-1-phenylpropan-2-ol

: 121-44-8
triethylamine

A: 1388835-90-2
(-)-(R)-1-phenylpropan-2-yl diethylcarbamate

B: 10304-81-1, 55449-46-2, 116698-42-1, 16583-73-6
(+)-2-chloro-1-phenylpropane

Conditions

Conditions	Yield
In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;	A 27% B 45%

...Expand

: 1517-68-6
(S)-1-phenylpropan-2-ol

: ((R)-2-Iodo-propyl)-benzene

Conditions

Conditions	Yield
With triphenylphosphine; diethylazodicarboxylate; methyl iodide at 20℃; for 24h;	40%

(S)-1-Phenyl-2-propanol Specification

The Benzeneethanol, α-methyl-, (αS)-, with the CAS registry number 1517-68-6, is also known as . It belongs to the product categories of Chiral Building Blocks; Simple Alcohols (Chiral); Synthetic Organic Chemistry. This chemical's molecular formula is C₉H₁₂O and molecular weight is 136.19. Its systematic name is called (2S)-1-phenylpropan-2-ol. You should keep container tightly closed and in a well-ventilated place.

Physical properties of Benzeneethanol, α-methyl-, (αS)-: (1)ACD/LogP: 1.71; (2)#H bond acceptors: 1; (3)#H bond donors: 1; (4)#Freely Rotating Bonds: 3; (5)Index of Refraction: 1.525; (6)Molar Refractivity: 41.92 cm³; (7)Molar Volume: 136.6 cm³; (8)Surface Tension: 37.3 dyne/cm; (9)Density: 0.996 g/cm³; (10)Flash Point: 85 °C; (11)Enthalpy of Vaporization: 48.24 kJ/mol; (12)Boiling Point: 220 °C at 760 mmHg; (13)Vapour Pressure: 0.067 mmHg at 25°C.

Preparation: this chemical can be prepared by 1-phenyl-propan-2-ol. The yield is about 43%.

Uses of Benzeneethanol, α-methyl-, (αS)-: it can be used to produce (+)(S)-2-chloro-1-phenyl-propane at temperature of 20 - 30 °C. This reaction will need reagent SOCl₂ with reaction time of 26 hours. The yield is about 65%.

When you are using this chemical, please be cautious about it as the following:
You should not breathe its gas/fumes/vapour/spray (appropriate wording to be specified by the manufacturer). In addition, you must avoid contacting it with skin and eyes.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@H](Cc1ccccc1)C
(2)InChI: InChI=1/C9H12O/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8,10H,7H2,1H3/t8-/m0/s1
(3)InChIKey: WYTRYIUQUDTGSX-QMMMGPOBBT

Product Name

S(+)-1-PHENYL-2-PROPANOL

Synthetic route

(S)-1-Phenyl-2-propanol Specification

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