20731-95-7

Basic information

• Product Name: (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester
• Synonyms: (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester;[R,(+)]-3-Hydroxy-2-phenylpropionic acid methyl ester;(-)-Methyl atrolactate;(-)-α-Methyl-D-mandelic acid methyl ester;(2R)-2-Hydroxy-2-phenylpropionic acid methyl ester;[R,(-)]-2-Hydroxy-2-phenylpropionic acid methyl ester;[R,(-)]-α-Hydroxyhydratropic acid methyl ester;2-Hydroxy-2-phenylpropanoic acid methyl ester
• CAS NO: 20731-95-7
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.20048
• Mol File: 20731-95-7.mol
• Article Data: 41

Chemical Properties

• Boiling Point: 127.5 °C(Press: 18 Torr)
• Appearance: /
• Density: 1.146±0.06 g/cm3(Predicted)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.26±0.29(Predicted)
• CAS DataBase Reference: (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester(20731-95-7)
• EPA Substance Registry System: (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester(20731-95-7)

Safety Data

• Hazardous Substances Data: 20731-95-7(Hazardous Substances Data)

Usage

Description

(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester, also known as (R)-Benzylglycidol, is an organic compound derived from benzeneacetic acid. It is a colorless liquid with a slightly sweet odor and is widely recognized for its utility as an intermediate in the synthesis of pharmaceuticals and agrochemicals. (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester is also frequently used as a chiral auxiliary in asymmetric synthesis and serves as a building block in the preparation of fine chemicals, making it a versatile and essential component in various chemical processes.

Uses

Used in Pharmaceutical Industry:
(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester is used as an intermediate for the synthesis of various pharmaceuticals. Its role in this industry is crucial, as it aids in the production of numerous important compounds that contribute to the development of life-saving medications.
Used in Agrochemical Industry:
In the agrochemical sector, (R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester is employed as an intermediate in the synthesis of various agrochemicals. Its contribution to this industry is significant, as it helps in the development of chemicals that are essential for enhancing crop protection and productivity.
Used in Asymmetric Synthesis:
(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester is utilized as a chiral auxiliary in asymmetric synthesis. This application is vital for the creation of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical processes due to their distinct biological activities.
Used in Fine Chemicals Preparation:
(R)-α-(Hydroxymethyl)benzeneacetic acid methyl ester also serves as a building block in the preparation of fine chemicals. Its use in this area is important, as it enables the synthesis of high-quality specialty chemicals that are used in a wide range of applications, from fragrances to advanced materials.

Upstream product

• 31508-44-8 2-phenylpropionic acid methyl ester 
• 15206-55-0 methyl 2-oxo-2-phenylacetate 
• 544-97-8 dimethyl zinc(II) 
• 67-56-1 methanol 
• 13113-71-8 (S)-Atrolactic acid 
• 69489-14-1 (S)-(+)-2-hydroxy-2-phenylpropanal 
• 97-72-3 2-Methylpropionic anhydride 
• 108-24-7 acetic anhydride 
• 123-62-6 propionic acid anhydride 
• 4358-87-6 (RS)-methyl mandelate 
• 74-88-4 methyl iodide 
• 175288-47-8 (R)-2-{[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-isopropyl-carbamoyloxy}-2-phenyl-propionic acid methyl ester 
• 186581-53-3 diazomethane 
• 515-30-0 2-phenyllactic acid 

Downstream Products

• 52181-20-1 2-hydroxy-N,2-diphenylpropanamide 
• 3784-22-3 (R)-1.1.2-triphenyl-propanediol-(1.2) 
• 6191-36-2 (R)-Atrolactinsaeureamid 
• 13448-81-2 (S)-methyl atrolactate 
• 13113-71-8 (S)-Atrolactic acid 
• 3966-30-1 (R)-Atrolactic acid 
• 13448-80-1 methyl R-(-)-atrolactate 
• 2406-22-6 (R)-1-phenyl-1,2-ethanediol 
• 515-30-0 2-phenyllactic acid 
• 2406-22-6 (2S)-2-phenylpropane-1,2-diol 
• 100058-89-7 (+/-)-methyl 2-methoxy-2-phenylpropionate 
• 7472-67-5 α-phenyl-α-methoxypropanoic acid 
• 98324-55-1 (1R,3R,4S:R)-(-)-menthyl 2-methoxy-2-phenylpropionate 
• 19748-93-7 1-propyl-3-phenyl-piperidine 

Relevant articles and documents

Electrocarboxylation of haloacetophenones at silver electrode

Electrocarboxylation of haloacetophenones 1 has been carried out in an undivided cell equipped with silver cathode and Mg sacrificial anode in N,N-dimethylformamide. The electroreduction behavior of these haloacetophenones at the Ag electrode was investig

Isothiourea-Catalyzed Acylative Kinetic Resolution of Tertiary α-Hydroxy Esters

A highly enantioselective isothiourea-catalyzed acylative kinetic resolution (KR) of acyclic tertiary alcohols has been developed. Selectivity factors of up to 200 were achieved for the KR of tertiary alcohols bearing an adjacent ester substituent, with both reaction conversion and enantioselectivity found to be sensitive to the steric and electronic environment at the stereogenic tertiary carbinol centre. For more sterically congested alcohols, the use of a recently-developed isoselenourea catalyst was optimal, with equivalent enantioselectivity but higher conversion achieved in comparison to the isothiourea HyperBTM. Diastereomeric acylation transition state models are proposed to rationalize the origins of enantiodiscrimination in this process. This KR procedure was also translated to a continuous-flow process using a polymer-supported variant of the catalyst.

Enantioselective addition of organozinc reagents to carbonyl compounds catalyzed by a camphor derived chiral γ-amino thiol ligand

In this article, the design and synthesis of the chiral camphor derived γ-amino thiol ligand 17 and its application in catalytic enantioselective carbon-carbon forming reactions through the addition of organozinc reagents to carbonyl compounds is described. The catalytic activity and enantioselectivity of ligand 17 is demonstrated in the enantioselective addition of various organozinc reagents to aldehydes and ketoesters, offering the corresponding alcohols in high yields and enantioselectivities. The role of the mercapto group in the highly enantioselective 1,2-addition reaction of organozincs to aldehyde is also discussed.