130272-52-5

Basic information

• Product Name: (R)-(+)-dimethyl-2-benzyl- succinate
• Synonyms: (R)-(+)-dimethyl-2-benzyl- succinate;(2R)-(Phenylmethyl)butanedioic acid dimethyl ester;(R)-Dimethyl 2-phenylmethylbutanedioate
• CAS NO: 130272-52-5
• Molecular Formula: C₁₃H₁₆O₄
• Molecular Weight: 236.2637
• Mol File: 130272-52-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 325.9 °C at 760 mmHg
• Flash Point: 157.3 °C
• Appearance: /
• Density: 1.113
• Vapor Pressure: 0.000224mmHg at 25°C
• Refractive Index: 1.5
• CAS DataBase Reference: (R)-(+)-dimethyl-2-benzyl- succinate(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(+)-dimethyl-2-benzyl- succinate(130272-52-5)
• EPA Substance Registry System: (R)-(+)-dimethyl-2-benzyl- succinate(130272-52-5)

Safety Data

• Hazardous Substances Data: 130272-52-5(Hazardous Substances Data)

Usage

General Description

(R)-(+)-dimethyl-2-benzyl-succinate is a chemical compound that belongs to the class of succinate esters. It is composed of two methyl groups, a benzyl group, and a succinate moiety. (R)-(+)-dimethyl-2-benzyl- succinate is chiral, with the (R)-enantiomer being the active form. It is commonly used as a building block in organic synthesis, particularly in the pharmaceutical industry for the production of various drugs and biologically active compounds. Additionally, it has potential applications in the field of materials science and as a chiral ligand in asymmetric catalysis. Its unique structure and chirality make it a valuable and versatile compound in various industries and research fields.

InChI:InChI=1/C13H16O4/c1-16-12(14)9-11(13(15)17-2)8-10-6-4-3-5-7-10/h3-7,11H,8-9H2,1-2H3/t11-/m1/s1

Upstream product

• 67-56-1 methanol 
• 201230-82-2 carbon monoxide 
• 5669-19-2 2-Benzyl-2-propenoic acid 
• 100-39-0 benzyl bromide 
• 6613-41-8 ethyl 3-phenylpyruvate 
• 20593-63-9 2-Benzylacrylic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 125702-14-9 (E)-3-(methoxycarbonyl)-4-phenylbut-3-enoic acid 
• 5653-88-3 trans-phenylitaconic acid 
• 65756-81-2 (Z)-2-benzylidenesuccinic acid 
• 65756-82-3 Z-methyl 4-(phenyl)-3-methoxycarbonylbut-3-enoate 
• 65859-90-7 dimethyl (E)-benzylidenesuccinate 
• 21307-97-1 (R)-2-benzylsuccinic acid 
• 186581-53-3 diazomethane 

Downstream Products

• 136282-52-5 N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine methyl ester 
• 136282-56-9 N-<(R)-2-benzyl-5-cyano-4-oxopentanoyl>-L-phenylalanine 
• 21307-97-1 (R)-2-benzylsuccinic acid 
• 126121-83-3 (R)-2-benzyl-5-cyano-4-oxopentanoic acid 

Relevant articles and documents

Hydrogen bonding makes a difference in the rhodium-catalyzed enantioselective hydrogenation using monodentate phosphoramidites

A new generation of monodentate phosphoramidite ligands bearing a primary amine moiety was found to display comparable or better efficiency than bisphosphines in the Rh-catalyzed asymmetric hydrogenation of challenging substrates, such as (Z)-methyl α-ace

Modular 1,1′-Ferrocenediyl-cored P-Stereogenic Diphosphines: ′′JDayPhos′′ Series and its Use in Rhodium(I)-Catalyzed Hydrogenation

A novel ferrocene-based P-stereogenic diphospine ligand series dubbed JDayPhos was developed, which rhodium(I) complexes of some of its members exhibited excellent enantioselectivity (up to >99% ee) and high activity in asymmetric hydrogenation of β-unsubstituted or -substituted itaconates and α-methylene-γ-oxo-carboxylates. (Figure presented.).

Synthesis and application of phosphinoferrocenylaminophosphine ligands for asymmetric catalysis

(Chemical Equation Presented) A new class of bidentate ligands utilizing a phosphine-aminophosphine structure has been prepared on a ferrocenylethyl backbone in a straightforward and scalable fashion from acetylferrocene. The unique property of the α-ferrocenyl carbonium ion that allows the replacement of a variety of "leaving groups" with retention of configuration greatly facilitates the synthesis, and a number of ligands have been prepared by varying the nitrogen and phosphorus substituents on the aminophosphine. These readily prepared phosphinoferrocenylaminophosphines, known as BoPhoz ligands, show surprising hydrolytic and air stability, with no degradation after 3 years open to the air. The rhodium complexes of these ligands show exceedingly high enantioselectivities (generally > 95% ee) and activities often in excess of 50 000 catalyst turnovers per hour for the asymmetric hydrogenation of a wide variety of dehydro-α-amino acid and itaconic acid derivatives. They also show high activity and good to excellent enantioselectivity for the hydrogenation of a number of α-ketoesters.