21037-34-3

Basic information

• Product Name: (R,R)-(-)-2,3-DIPHENYLSUCCINIC ACID
• Synonyms: (R,R)-(-)-2,3-DIPHENYLSUCCINIC ACID;(R,R)-2,3-DIPHENYLSUCCINIC ACID;(R,R)-2,3-Diphenylbutanedioicacid
• CAS NO: 21037-34-3
• Molecular Formula: C₁₆H₁₄O₄
• Molecular Weight: 270.28
• Product Categories: Chiral Compound
• Mol File: 21037-34-3.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 360.2°C at 760 mmHg
• Flash Point: 185.8°C
• Appearance: /
• Density: 1.307g/cm³
• Vapor Pressure: 8.13E-06mmHg at 25°C
• Refractive Index: 1.62
• PKA: 3.38±0.10(Predicted)
• CAS DataBase Reference: (R,R)-(-)-2,3-DIPHENYLSUCCINIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (R,R)-(-)-2,3-DIPHENYLSUCCINIC ACID(21037-34-3)
• EPA Substance Registry System: (R,R)-(-)-2,3-DIPHENYLSUCCINIC ACID(21037-34-3)

Safety Data

• Hazardous Substances Data: 21037-34-3(Hazardous Substances Data)

Usage

General Description

"(R,R)-(-)-2,3-DIPHENYLSUCCINIC ACID," also known as (R,R)-(-)-2,3-bis(phenyl)butanedioic acid, is a chemical compound. Its molecular formula is C16H14O4 and it has a molecular weight of 270.28 g/mol. Like all succinic acids, it contains a succinate group, which is a carboxylic acid derivative. Its structure consists of two phenyl groups attached to a succinic acid, resulting in a chiral molecule. Due to its chiral nature, this substance occurs in two different enantiomers, or mirror image forms, designated as R,R and S,S. The R,R form is considered to be more bioactive. The uses of this chemical are not very extensively documented, but it can potentially be used as a reagent in organic synthesis. Its risk and safety statements declare that it may cause eye, skin, and respiratory irritation and it should be kept away from open flames, hot surfaces, and direct sunlight.

InChI:InChI=1/C16H14O4/c17-15(18)13(11-7-3-1-4-8-11)14(16(19)20)12-9-5-2-6-10-12/h1-10,13-14H,(H,17,18)(H,19,20)/t13-,14-/m0/s1

Upstream product

• 4870-65-9 2-bromophenylacetic acid 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 60-29-7 diethyl ether 
• 87338-61-2 bibenzyl-α,α'-diyl dipotassium 
• 15719-64-9 methylammonium carbonate 
• 3059-23-2 dl-Diethyl 2,3-diphenylsuccinate 
• 141-52-6 sodium ethanolate 
• 64-17-5 ethanol 
• 3059-23-2 diethyl meso-α,α'-diphenylsuccinate 
• 5798-79-8 bromo-phenyl-acetonitrile 
• 4755-72-0 Chloro-phenyl-acetic acid 
• 920-39-8 isopropylmagnesium bromide 
• 114-70-5 sodium phenylacetate 
• 110-86-1 pyridine 

Downstream Products

• 19020-59-8 dimethyl α,α'-diphenylsuccinate 
• 25169-81-7 meso-2,3-diphenylsuccinic acid dimethyl ester 
• 874504-98-0 3,4-diphenyl-1-propyl-pyrrolidine-2,5-dione 
• 20714-91-4 meso-2,3-diphenyl-succinic acid monoethyl ester 
• 102663-44-5 1-(1-methyl-pentyl)-3,4-diphenyl-pyrrolidine-2,5-dione 
• 74431-38-2 (2S,3S)-(+)-2,3-Diphenylsuccinic acid 
• 4808-48-4 2,3-diphenylmaleic anhydride 
• 875236-29-6 1-allyl-3,4-diphenyl-pyrrolidine-2,5-dione 
• 1225-13-4 (2S,3S)-(dl)-2,3-diphenylsuccinic acid 
• 74402-23-6 (+/-)-3-oxo-2-phenyl-1-indancarboxylic acid 
• 139556-45-9 (2R,3R)-2,3-dicyclohexylsuccinic acid 
• 1225-13-4 2,3-Diphenyl-succinic acid 
• 1225-13-4 2,3-Diphenyl-succinic acid 
• 286936-47-8 N-(α-Methylbenzyl)-3,4-diphenylpyrrolidin-2,5-dione 

Relevant articles and documents

Efficient electrochemical dicarboxylation of phenyl-substituted alkenes: Synthesis of 1-phenylalkane-1,2-dicarboxylic acids

Electrochemical dicarboxylation of phenyl-substituted alkenes in the presence of atmospheric pressure of carbon dioxide with a platinum plate cathode and a magnesium rod anode readily took place efficiently in a DMF solution containing 0.1 M Et4NClO4 to give the corresponding 1,2-dicarboxylic acids in high yields.

Dependence of the reactivities of titanium enolates on how they are generated: Diastereoselective coupling of phenylacetic acid esters using titanium tetrachloride

Oxidative coupling of phenylacetic acid esters was easily achieved by treating the esters with TiCl4 and then adding Et3N to the resulting solution. The products consisted of dl- and meso-2,3-diphenylsuccinic acid esters with the Claisen condensation product, and the ratio of these products depended on the reaction conditions. Reaction conditions suitable for high dl selectivity were determined, and a dimer of titanium enolate was postulated as an intermediate responsible for the high dl selectivity. The selectivities were compared with those in known oxidative couplings in which titanium enolate intermediates are prepared through lithium enolates and silyl enol ethers. The results suggest that the reactivities of titanium enolates intermediates depend on how they are generated.

Influence of β-arranged substituents in chiral seven-membered rhodium diphosphine rings on asymmetric hydrogenation of amino acid precursors

Investigations concerning the optical induction in asymmetric hydrogenation reactions confirm the stereochemical control function of mono- and di-substituents in seven-membered chelate ring diphosphines, whereby the bulkiness of substituents in the backbone of the ligands is reflected in higher enantioselectivities.