947-94-4

Basic information

• Product Name: 2-Acetoxy-2-phenylacetic acid methyl ester
• Synonyms: 2-Acetoxy-2-phenylacetic acid methyl ester;α-(Acetyloxy)benzeneacetic acid methyl ester
• CAS NO: 947-94-4
• Molecular Formula: C₁₁H₁₂O₄
• Molecular Weight: 208.21
• Mol File: 947-94-4.mol
• Article Data: 13

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-Acetoxy-2-phenylacetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Acetoxy-2-phenylacetic acid methyl ester(947-94-4)
• EPA Substance Registry System: 2-Acetoxy-2-phenylacetic acid methyl ester(947-94-4)

Safety Data

• Hazardous Substances Data: 947-94-4(Hazardous Substances Data)

Usage

Abbreviation

APMA

Physical State

Colorless to light yellow liquid

Primary Use

Reagent in organic synthesis

Common Applications

Production of pharmaceuticals
Production of fine chemicals

Functional Groups

Acetoxy group ( -\textOCOCH3 )
Phenyl group ( -\textC6\textH5 )

Chemical Classification

Acetic acid ester

Role in Pharmaceutical Industry

Used in the preparation of various pharmaceutical compounds

Potential Medical Applications

Development of new drugs
Medical treatments

Research Use

Activation of calpain, an enzyme involved in cellular signaling pathways

Field of Research Application

Cellular biology
Molecular biology

Upstream product

• 108-05-4 vinyl acetate 
• 4358-87-6 (RS)-methyl mandelate 
• 108-24-7 acetic anhydride 
• 157339-06-5 (CH₃(CH₂)3)3SnCH(C₆H₅)CH₃COO 
• 29071-09-8 2-acetoxy-2-phenylacetic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 100-52-7 benzaldehyde 
• 1071508-40-1 (α-(acetyloxy)benzyl)tributylstannane 
• 51019-43-3 (R)-(-)-O-acetylmandelic acid 
• 611-71-2 MANDELIC ACID 
• 868532-34-7 acetic acid 2-oxo-1-phenyl-2-(2-thioxo-oxazolidin-3-yl)-ethyl ester 
• 67-56-1 methanol 
• 20698-91-3 (R)-methyl mandelate 
• 876-27-7 4-chlorophenyl acetate 

Relevant articles and documents

Chemoenzymatic Preparation of Enantiomerically Enriched (R)-(–)-Mandelic Acid Derivatives: Application in the Synthesis of the Active Agent Pemoline

The enantioselective resolution of several racemic derivatives of mandelic acid methyl ester catalyzed by lipases from Pseudomonas fluorescens (Amano AK) or Burkholderia cepacia (Amano PS-C II and Amano PS-IM) has been achieved. A gram-scale lipase-mediated kinetic resolution approach has been developed that allows the facile synthesis of the corresponding methyl (R)-(–)-mandelates with excellent enantiomeric excesses (up to >99 % ee) and reaction enantioselectivity (E values up to >200). The dopaminergic agent pemoline, used in the treatment of attention-deficit hyperactivity disorder (ADHD) and narcolepsy, was synthesized with 98 % ee in a straightforward route by condensing the prepared methyl (R)-(–)-mandelate with guanidine hydrochloride under basic conditions. The desired (R)-(+)-pemoline in optically pure form (>99 % ee) was obtained after two recrystallizations from ethanol. However, it was confirmed by chiral HPLC that optically active pemoline undergoes racemization in methanol solution.

The assignment of the configuration for α-hydroxy acid esters using a CEC strategy

A simple and efficient 1H NMR method for determining the absolute configuration of chiral α-hydroxy acid esters using a competing enantioselective conversion (CEC) strategy was developed. The α-hydroxy acid esters were acylated in the presence

Kinetic resolution of α-acetoxy N-acyl oxazolidinethiones by a chiral O-nucleophilic acyl transfer catalyst

The kinetic resolution of α-acetoxy N-acyl oxazolidinethiones using the chiral, nonracemic O-nucleophilic acyl transfer catalyst 8 is described. The reaction proceeds on a variety of substrates in excellent yields, with s-factors ranging from 17 to 31. Copyright