(+)-Phenylacetyl Carbinol

Base Information

• Chemical Name: (+)-Phenylacetyl Carbinol
• CAS No.: 53439-91-1
• Molecular Formula: C9H10O2
• Molecular Weight: 150.177
• European Community (EC) Number: 805-150-8
• UNII: 57T7N5C73Q
• Nikkaji Number: J53.526E
• Wikidata: Q27261522
• Mol file: 53439-91-1.mol

Synonyms:53439-91-1;(+)-Phenylacetyl Carbinol;(1S)-1-HYDROXY-1-PHENYLPROPAN-2-ONE;Phenylacetyl carbinol, (+)-;l-phenylacetylcarbinol;(S)-1-Hydroxy-1-phenyl-2-propanone;L-Phenylacetyl Carbinol;(S)-phenylacetylcarbinol;(S)-1-Hydroxy-1-phenylpropanone;(S)-Phenylacetyl Carbinol;2-Propanone, 1-hydroxy-1-phenyl-, (1S)-;(S)-1-Hydroxy-1-phenylpropan-2-one;(S)-PAC;UNII-57T7N5C73Q;57T7N5C73Q;rel-(1R)-1-hydroxy-1-phenylpropan-2-one;(+)-phenylacetylcarbinol;(1S)-phenylacetylcarbinol;(S)-(+)-phenylacetylcarbinol;SCHEMBL9221845;CHEBI:149670;AKOS027324276;(1S)-1-Hydroxy-1-phenyl-2-propanone;CS-0232438;EN300-1272246;EN300-6735034;Q27261522

Chemical Property of (+)-Phenylacetyl Carbinol

Chemical Property:

• Boiling Point: 253.3±20.0 °C(Predicted)
• PKA: 12.33±0.20(Predicted)
• PSA: 37.30000
• Density: 1.119±0.06 g/cm3(Predicted)
• LogP: 1.30900
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 150.068079557
• Heavy Atom Count: 11
• Complexity: 137

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C(C1=CC=CC=C1)O
• Isomeric SMILES: CC(=O)[C@H](C1=CC=CC=C1)O
• Uses: L-Phenylacetylcarbinol L-Phenylacetylcarbinol ( (L-PAC) obtained by biotransformation of benzaldehyde.

Technology Process of (+)-Phenylacetyl Carbinol

There total 36 articles about (+)-Phenylacetyl Carbinol 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:

methyl magnesium iodide (917-64-6) + (R)-2-phenyl-2-(trimethylsiloxy)acetonitrile (120443-82-5) → (R)-1-hydroxy-1-phenyl-2-propanone (1798-60-3) + (S)-phenylacetylcarbinol (53439-91-1)

Guidance literature:

With hydrogenchloride; Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) ether, reflux, 2 h;

DOI:10.1071/CH9902045

Reference yield:

1-phenyl-2-trimethylsiloxy-1-propene (43108-63-0) → (R)-1-hydroxy-1-phenyl-2-propanone (1798-60-3) + (S)-phenylacetylcarbinol (53439-91-1)

Guidance literature:

With (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine; methyllithium; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) HMPA, THF, 0 deg C, 1h; 2.) -78 deg C;

DOI:10.1016/S0040-4039(01)80611-0

Reference yield:

1-phenyl-acetone (103-79-7,136675-26-8) → (R)-1-hydroxy-1-phenyl-2-propanone (1798-60-3) + (S)-phenylacetylcarbinol (53439-91-1)

Guidance literature:

With (+)-(2S,8aS)-(camphorylsulfonyl)oxaziridine; lithium diisopropyl amide; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts; 1.) HMPA, THF, -78 deg C; 2.) HMPA, -78 deg C;

DOI:10.1016/S0040-4039(01)80611-0

upstream raw materials:

methyl magnesium iodide

(R)-2-phenyl-2-(trimethylsiloxy)acetonitrile

1-phenyl-2-trimethylsiloxy-1-propene

1-phenyl-acetone

Downstream raw materials:

benzaldehyde

(1S,2S)-1-phenyl-1,2-propanediol

(1S,2R)-(+)-norphedrine

(1S,2S)-2-amino-1-phenylpropanol

Refernces

• 1、 Andreu, Cecilia,del Olmo, Marcellí. "Whole-Cell Biocatalysis in Seawater: New Halotolerant Yeast Strains for the Regio- and Stereoselectivity Reduction of 1-Phenylpropane-1,2-Dione in Saline-Rich Media". . p. 1621 - 1628. Retrieved 2020/03/05.
• 2、 Ruiz, Doris,M?ki-Arvela, P?ivi,Aho, Atte,Chiment?o, Ricardo,Claver, Carmen,Godard, Cyril,Fierro, José L.G.,Murzin, Dmitry Yu.. "Immobilized chiral rhodium nanoparticles stabilized by chiral P-ligands as efficient catalysts for the enantioselective hydrogenation of 1-phenyl-1,2-propanedione". . . Retrieved 2019/08/26.