147256-18-6

Basic information

• Product Name: 1,2-Ethanediol, 1-phenyl-, 2-acetate, (1R)-
• CAS NO: 147256-18-6
• Molecular Formula: C10H12O3
• Molecular Weight: 180.203
• Mol File: 147256-18-6.mol
• Article Data: 14

Chemical Properties

• CAS DataBase Reference: 1,2-Ethanediol, 1-phenyl-, 2-acetate, (1R)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1,2-Ethanediol, 1-phenyl-, 2-acetate, (1R)-(147256-18-6)
• EPA Substance Registry System: 1,2-Ethanediol, 1-phenyl-, 2-acetate, (1R)-(147256-18-6)

Safety Data

• Hazardous Substances Data: 147256-18-6(Hazardous Substances Data)

Upstream product

• 108-05-4 vinyl acetate 
• 93-56-1 phenylethane 1,2-diol 
• 581-55-5 benzylidene 1,1-diacetate 
• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 
• 108-24-7 acetic anhydride 
• 100-42-5 styrene 
• 64-19-7 acetic acid 
• 98-86-2 acetophenone 
• 70-11-1 α-bromoacetophenone 
• 532-27-4 1-chloroacetophenone 
• 2243-35-8 2-acetoxyacetophenone 
• 108-22-5 Isopropenyl acetate 
• 127707-63-5 2-phenyl-2-hydroxyethyl acetate 

Downstream Products

• 16355-00-3 (R)-1-phenyl-1,2-ethanediol 

Relevant articles and documents

A Three-Dimensional Predictive Active Site Model for Lipase from

A three-dimensional active site model of lipase from Pseudomonas cepacia - one of the most popular lipases in organic synthesis - was developed on the basis of the kinetic resolution of 3-(aryloxy)propan-2-ols. Size and shape of both hydrophobic binding pockets of the active site of this lipase were determined by substrate mapping in combination with molecular modeling for substrates and nonsubstrates. This model explains and predicts whether a compound is accepted as a substrate or not and allows to assess the enantiomer selectivity of the lipase-catalyzed reaction.

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio-and Stereoselective Acylation of Alcohols

Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.

Enantioselective Vicinal Diacetoxylation of Alkenes under Chiral Iodine(III) Catalysis

A procedure for the intermolecular enantioselective dioxygenation of alkenes under iodine(III) catalysis has been developed. This protocol employs Selectfluor as the terminal oxidant together with a defined C 2-symmetric aryl iodide as the organocatalyst. This enantioselective reaction proceeds under mild conditions and converts a series of terminal and internal styrenes into the corresponding vicinal diacetoxylation products with up to 96% ee.

Chemoenzymatic synthesis of enantiomerically pure 1,2-diols employing immobilized lipase in the ionic liquid [bmim]PF6

Significantly enhanced enantioselectivity in the enzymatic kinetic resolution of 1,2-diols employing immobilized lipase from Pseudomonas cepacia (PS-C, 'Amano') results from the use of the ionic liquid [bmim]PF6 as reaction medium.