97415-09-3

Basic information

• Product Name: D-(-)-MANDELIC ACID BENZYL ESTER
• Synonyms: (R)-BENZYL MANDELATE;ALPHA-HYDROXY-BENZENEACETIC ACID, PHENYLMETHYL ESTER;D-(-)-MANDELIC ACID BENZYL ESTER;BENZYL D-(-)-MANDELATE;BENZYL (R)-(-)-MANDELATE;Benzyl-(R)-Mandelate / Benzyl-(D)-Mandelate;(R)-Benzyl 2-hydroxy-2-phenylacetate;Benzeneacetic acid, α-hydroxy-, phenylmethyl ester, (αR)-
• CAS NO: 97415-09-3
• Molecular Formula: C₁₅H₁₄O₃
• Molecular Weight: 242.27
• EINECS: 1312995-182-4
• Product Categories: Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry;Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 97415-09-3.mol
• Article Data: 27

Chemical Properties

• Melting Point: 104-107 °C(lit.)
• Boiling Point: 387℃
• Flash Point: 163℃
• Appearance: /
• Density: 1.204
• Vapor Pressure: 1.13E-06mmHg at 25°C
• Refractive Index: -34 ° (C=1, CH3CN)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.15±0.20(Predicted)
• CAS DataBase Reference: D-(-)-MANDELIC ACID BENZYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: D-(-)-MANDELIC ACID BENZYL ESTER(97415-09-3)
• EPA Substance Registry System: D-(-)-MANDELIC ACID BENZYL ESTER(97415-09-3)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 97415-09-3(Hazardous Substances Data)

Usage

Description

(R)-benzyl Mandelate is a synthetic intermediate useful for pharmaceutical synthesis.

Uses

Different sources of media describe the Uses of 97415-09-3 differently. You can refer to the following data:
1. Benzyl (R)-(-)-mandelate can be employed as reactant to synthesize: (S)-α-Hydroxy-N-(2-phenylethyl)benzenepropanamide (α-hydroxyamides) by enzyme catalyzed amidation reaction. Optically pure (R)- monomethyl esters of 3-[(tert-butyldimethylsilyl)oxy]pentanedioic acid, which is employed in the preparation of HMG-CoA reductase inhibitors. O-Ibuprofenylmandelic acid via acylation reaction with optically active ibuprofen and subsequent hydrogenation. Benzyl (R)-2-fluoro-2-phenylacetate via deoxyfluorination of alcohols using AlkylFluor.It can also be used to prepare HMG-CoA reductase inhibitors.
2. D-(-)-Mandelic Acid Benzyl Ester is a useful reagent for the preparation of a pharmaceutical composition for treating atopic dermatitis.

InChI:InChI=1/C15H14O3/c16-14(13-9-5-2-6-10-13)15(17)18-11-12-7-3-1-4-8-12/h1-10,14,16H,11H2/t14-/m1/s1

Upstream product

• 908094-04-2 phenyldiazomethane 
• 611-71-2 MANDELIC ACID 
• 100-51-6 benzyl alcohol 
• 91-01-0 1,1-Diphenylmethanol 
• 144-55-8 sodium hydrogencarbonate 
• 102-16-9 benzyl 2-phenylacetate 
• 14758-41-9 2-Hydroxy-2-phenyl-1,1,1-tris-(phenylmercapto)-aethan 
• 25726-04-9 phenylglyoxylyl chloride 
• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 611-73-4 Benzoylformic acid 
• 62977-82-6 benzyl oxo(phenyl)acetate 
• 100-39-0 benzyl bromide 
• 62173-99-3 benzyl 2-hydroxy-2-phenylacetate 
• 611-71-2 (R)-Mandelic Acid 

Downstream Products

• 129910-28-7 (1S,2R,3S,4R)-Bicyclo<2.2.1>hept-5-ene-2,3-dicarboxylic Acid 2-(Benzyl (R)-mandelate) 
• 131564-23-3 (1R,2S,3R,4S)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester 
• 129910-29-8 (1R,2R,3S,4S)-Bicyclo<2.2.1>heptane-2,3-dicarboxylic Acid 2-<(R)-Mandelic acid> Ester 
• 134940-39-9 (1R,2R,3S,4S)-Bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester 
• 134940-39-9 (1S,2S,3R,4R)-Bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester 
• 131466-59-6 (1R,2S,3R,4S)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester 
• 131564-21-1 (1S,2R,3S,4R)-7-Oxa-bicyclo[2.2.1]heptane-2,3-dicarboxylic acid mono-((R)-benzyloxycarbonyl-phenyl-methyl) ester 
• 130362-19-5 (1R,2S,3R,4S)-2-<(R)-Mandeloxycarbonyl>-7-oxabicyclo<2.2.1>heptane-3-carboxylic Acid 
• 14007-02-4 butyl mandelate 
• 341925-84-6 (R)-Benzyloxy-phenyl-acetic acid benzyl ester 
• 62977-82-6 benzyl oxo(phenyl)acetate 
• 165337-03-1 4-(benzyloxy)-5-phenylfuran-2(5H)-one 
• 1186216-42-1 benzyl O-(tert-butyl)mandelate 
• 62173-99-3 (S)-benzyl 2-hydroxy-2-phenylacetate 

Relevant articles and documents

Direct Aerobic α-Hydroxylation of Arylacetates for the Synthesis of Mandelates

Aerobic α-hydroxylation of α-methylene esters has proven challenging due to overoxidation and hydrolysis of the materials. In this article, KOtBu-promoted TBAB-catalyzed α-hydroxylation of α-methylene aryl esters using O2as the oxyge

Ester Formation via Symbiotic Activation Utilizing Trichloroacetimidate Electrophiles

Trichloroacetimidates are useful reagents for the synthesis of esters under mild conditions that do not require an exogenous promoter. These conditions avoid the undesired decomposition of substrates with sensitive functional groups that are often observed with the use of strong Lewis or Br?nsted acids. With heating, these reactions have been extended to benzyl esters without electron-donating groups. These inexpensive and convenient methods should find application in the formation of esters in complex substrates.

Silica-supported HClO4 promotes catalytic solvent- and metal-free O-H insertion reactions with diazo compounds

Solvent-free O-H insertion reactions in the presence of diazo carbonyl compounds were carried-out in very mild conditions. Unlike the traditional metal-catalysed version, employing rhodium acetate dimer, this method uses eco-friendly silica-supported HClO4 as the catalyst. Only 0.3 mol% of this Br?nsted acid catalyst, that can also be recycled several times, is necessary to guarantee very good yields (up to 97%) in the O-H insertion reactions. Reaction set-up is simple and permitted the preparation of forty-three α-hydroxy and α-alkoxy esters/ketones in just 1 h and at room temperature.