(S)-1-Phenylethanol

Base Information

• Chemical Name: (S)-1-Phenylethanol
• CAS No.: 1445-91-6
• Molecular Formula: C8H10O
• Molecular Weight: 122.167
• Hs Code.: 29062990
• European Community (EC) Number: 604-424-2
• UNII: 2MIC4QLY2X
• DSSTox Substance ID: DTXSID4073259
• Nikkaji Number: J56.778G
• Wikidata: Q26841260
• Metabolomics Workbench ID: 50465
• ChEMBL ID: CHEMBL348446
• Mol file: 1445-91-6.mol

Synonyms:(S)-1-Phenylethanol;1445-91-6;(S)-(-)-1-Phenylethanol;(1S)-1-phenylethanol;(1S)-1-Phenylethan-1-Ol;1-Phenylethanol, (S)-;(-)-Methyl phenyl carbinol;(s)-1-phenyl-ethanol;(S)-(-)-phenylethanol;(s)-1-phenyl-1-ethanol;(S)-1-phenylethan-1-ol;(S)-(-)-1-Phenylethyl Alcohol;UNII-2MIC4QLY2X;S-1-PHENYLETHANOL;2MIC4QLY2X;(S)-1-Phenethyl alcohol;Benzenemethanol, .alpha.-methyl-, (.alpha.S)-;(S)-1-Phenylethyl alcohol;(S)-alpha-methylbenzenemethanol;CHEBI:16346;(S)-(-)-alpha-Methylbenzyl alcohol;MFCD00064264;Benzenemethanol, alpha-methyl-, (S)-;[S]-1-phenylethanol;Benzenemethanol, .alpha.-methyl-, (S)-;1-Phenylethanol #;(1S)-1-PHENYL-ETHANOL;(S)-(-)-sec-Phenethyl Alcohol;(S)-phenylethanol;(S)-(-)-Sec-Phenylethyl alcohol;(-)-1-phenylethanol;(-)-sec-phenethyl alcohol;SCHEMBL7144;1-phenyl-(1S)-ethan-1-ol;CHEMBL348446;(S)-PHENYLMETHYLCARBINOL;DTXSID4073259;1-PHENYLETHANOL, (-)-;(-)-.ALPHA.-PHENYLETHANOL;(-)-1-PHENYL-1-ETHANOL;(-)-1-PHENYLETHYL ALCOHOL;(-)-(S)-1-PHENYLETHANOL;(AlphaS)-alpha-methylbenzenemethanol;Benzenemethanol, a-methyl-, (aS)-;HY-78093A;s3365;(S)-(-)-1-Phenylethanol, 97%;AKOS016842975;AM84405;(-)-.ALPHA.-PHENETHYL ALCOHOL;(-)-.ALPHA.-METHYLBENZYL ALCOHOL;AS-13396;BP-10717;SS1;Benzenemethanol, alpha-methyl-, (alphaS)-;CS-0007824;P0796;EN300-87752;F13077;A808240;(S)-(-)-1-Phenylethanol, for chiral derivatization;J-007970;J-501784;Q26841260;Z360055168;(S)-(-)-1-Phenylethanol, >=98.5% (sum of enantiomers, GC);(S)-(-)-1-Phenylethanol, for chiral derivatization, >=99.0%;(S)-(-)-1-Phenylethanol, ChiPros(R), produced by BASF, 98%

Chemical Property of (S)-1-Phenylethanol

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.139mmHg at 25°C
• Melting Point: 9-11 °C(lit.)
• Refractive Index: n20/D 1.528
• Boiling Point: 206.917 °C at 760 mmHg
• PKA: 14.43±0.20(Predicted)
• Flash Point: 91.171 °C
• PSA: 20.23000
• Density: 1.014 g/cm³
• LogP: 1.73990
• Storage Temp.: 2-8°C
• Solubility.: 20g/l
• Water Solubility.: 20 g/L (20 ºC)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 122.073164938
• Heavy Atom Count: 9
• Complexity: 74.6

Purity/Quality:

99%, ^*data from raw suppliers

(S)-(-)-1-Phenylethyl Alcohol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-38-41-36/37/38
• Safety Statements: 26-39-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Classes -> Alcohols and Polyols, Other
• Canonical SMILES: CC(C1=CC=CC=C1)O
• Isomeric SMILES: C[C@@H](C1=CC=CC=C1)O
• General Description: (S)-(-)-1-Phenylethanol is a chiral secondary alcohol that can be synthesized with high enantioselectivity (up to 98% ee) via palladium-catalyzed asymmetric hydrosilylation of styrenes, followed by oxidation. The reaction's high enantioselectivity is attributed to the use of optimized chiral monophosphine ligands, such as (R)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino-1,1′-binaphthyl (2g), which promote fast β-hydrogen elimination over reductive elimination in the catalytic cycle. (S)-(-)-1-PHENYLETHANOL and its derivatives are valuable chiral building blocks in organic synthesis, with applications in pharmaceuticals and fine chemicals. The study highlights the importance of ligand design in achieving high enantioselectivity and catalytic efficiency.

Technology Process of (S)-1-Phenylethanol

There total 549 articles about (S)-1-Phenylethanol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 96.8%

Isopropenyl acetate (108-22-5) + 1-Phenylethanol (98-85-1,13323-81-4) → (R)-1-phenylethyl acetate + styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + (S)-1-phenylethanol (1445-91-6) + acetophenone (98-86-2)

Guidance literature:

Novozym 435; Zr-beta; In hexane; at 60 ℃; for 6h;

DOI:10.1002/chem.200600723

Reference yield: 60.0%

(R)-(1-bromoethyl)benzene (1459-14-9) → styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + ethylbenzene (100-41-4,27536-89-6) + (S)-1-phenylethanol (1445-91-6) + (R)-1-phenylethanol (1517-69-7) + (RR)/(SS)-2,3-diphenylbutane (5789-35-5) + 2,3-diphenylbutane (4613-11-0,1245924-68-8) + 1,1'-(1,2-ethanediyl)bisbenzene (103-29-7)

Guidance literature:

With ISOPROPYLAMIDE; copper; at 70 ℃; for 2h;

DOI:10.1134/S1070363214090047

Reference yield: 53.0%

Isopropenyl acetate (108-22-5) + 1-Phenylethanol (98-85-1,13323-81-4) → (S)-1-phenylethyl acetate + (R)-1-phenylethyl acetate + styrene (100-42-5,25038-60-2,25247-68-1,28213-80-1,28325-75-9,79637-11-9,9003-53-6) + (S)-1-phenylethanol (1445-91-6)

Guidance literature:

Novozym 435; Zr-beta; In various solvent(s); at 60 ℃; for 6h;

DOI:10.1002/chem.200600723

upstream raw materials:

1-Phenylethanol

(R)-1-phenyl-ethyl-amine

(S)-N,N-dimethyl-1-phenylethylamine

tert-butyl-((S)-1-phenyl-ethyl)-peroxide

Downstream raw materials:

(S)-(1-chloroethyl)benzene

(R)-1-chloro-1-phenylethane

ethyl-((R)-1-phenyl-ethyl)-ether

(Ξ)-ethyl-((S)-1-phenyl-ethyl)-sulfite

Refernces

Asymmetric hydrosilylation of styrenes catalyzed by palladium-MOP complexes: Ligand modification and mechanistic studies

10.1021/jo001614p

The research investigates the enantioselective hydrosilylation of styrene derivatives using palladium complexes with various chiral monophosphine ligands derived from 1,1′-binaphthyl axial chirality. The primary goal is to enhance the enantioselectivity of the reaction by modifying the ligands and to elucidate the underlying mechanisms. The study found that the ligand (R)-2-bis[3,5-bis(trifluoromethyl)phenyl]phosphino-1,1′-binaphthyl (2g) achieved the highest enantioselectivity, yielding (S)-1-phenylethanol with 98% enantiomeric excess (ee) after oxidation of the hydrosilylation product. This ligand also efficiently catalyzed the asymmetric hydrosilylation of substituted styrenes, producing chiral benzylic alcohols with over 96% ee. Mechanistic studies, including deuterium-labeling experiments, revealed that the fast β-hydrogen elimination from the alkylpalladium intermediate, compared to reductive elimination, is crucial for the high enantioselectivity observed with ligand 2g. The research concludes that the electronic and steric properties of the ligand significantly influence the reaction's enantioselectivity and catalytic activity, providing valuable insights for further ligand design and optimization in asymmetric catalysis.

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