4036-30-0

Basic information

• Product Name: (S)-(+)-Phenylsuccinic acid
• Synonyms: (S)-(+)-PHENYLSUCCINIC ACID;(S)-2-PHENYL SUCCINIC ACID;(+)-PHENYL SUCCINIC ACID;(S)-(+)-Phenylsuccinicacid,98%;(S)-(+)-Phenylsuccinic acid, 99+%;(S)-2-PHENYL SUCCINIC ACID 98.5%;Butanedioic acid, phenyl-, (S)-;(S)-2-Phenylbutanedioic acid
• CAS NO: 4036-30-0
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• EINECS: 223-719-3
• Product Categories: Miscellaneous;Carboxylic Acids (Chiral);Chiral Building Blocks;Synthetic Organic Chemistry;Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 4036-30-0.mol
• Article Data: 10

Chemical Properties

• Melting Point: 173-176 °C
• Boiling Point: 290.62°C (rough estimate)
• Flash Point: 154.2 °C
• Appearance: almost white micro-crystalline powder
• Density: 1.2534 (rough estimate)
• Vapor Pressure: 0.000306mmHg at 25°C
• Refractive Index: 147.5 ° (C=2, EtOH)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: within almost transparency in Methanol
• PKA: 3.60±0.10(Predicted)
• BRN: 2616723
• CAS DataBase Reference: (S)-(+)-Phenylsuccinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(+)-Phenylsuccinic acid(4036-30-0)
• EPA Substance Registry System: (S)-(+)-Phenylsuccinic acid(4036-30-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26
• WGK Germany: 3
• Hazardous Substances Data: 4036-30-0(Hazardous Substances Data)

Usage

Chemical Properties

almost white micro-crystalline powder

InChI:InChI=1/C10H10O4/c11-9(12)6-8(10(13)14)7-4-2-1-3-5-7/h1-5,8H,6H2,(H,11,12)(H,13,14)/t8-/m0/s1

Upstream product

• 635-51-8 2-phenylsuccinic acid 
• 78920-22-6 4-hydroxy-3-phenylbutyro-1,4-lactone 
• 89358-92-9 2,3-dideoxy-3C-phenyl-D-manno-heptono-1,4-lactone 
• 1232144-14-7 (S)-methyl-3-(6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-4-oxo-4H-pyran-2-yl)-3-phenylpropanoate 
• 201230-82-2 carbon monoxide 
• 492-38-6 2-phenylacrylic acid 

Downstream Products

• 3975-92-6 (S)-(+)-2-cyclohexylbutanedioic acid 
• 116668-56-5 (S)-(+)-3-phenyldihydrofuran-2,5-dione 
• 6837-05-4 (2S)-2-phenylbutane-1,4-diol 
• 134920-62-0 (2S)-2-phenylbutane-1,4-diol-di-p-toluenesulfonate 
• 83174-29-2 (S)-(+)-cyclohexylsuccinic anhydride 
• 72379-83-0 (S)-N-methyl-2-phenyl-succinamic acid 
• 92963-62-7 (+)-(2S)-4-anilino-4-oxo-2-phenylbutanoic acid 
• 6017-78-3 (S)-1,3-diphenylpyrrolidine-2,5-dione 
• 61548-78-5 (S)-(1,4-dibromobutan-2-yl)benzene 
• 15463-92-0 (S)-(+)-dimethyl 2-phenylsuccinate 
• 883901-38-0 (S)-3-(4-amino-phenyl)-1-propyl-pyrrolidine 
• 883901-37-9 (S)-3-(4-nitro-phenyl)-1-propyl-pyrrolidine 
• 164653-83-2 methanesulfonic acid (S)-4-methanesulfonyloxy-3-phenyl-butyl ester 

Relevant articles and documents

Optical Resolution of (+/-)-Phenylsuccinic Acid by Using (-)-Proline as Resolving Agent

A solution of equimolar mixture of (+/-)-phenylsuccinic acid ((+/-)-PSA) and (-)-proline ((-)-Pro) in ethanol or its suspension in 2-propanol selectively gave a salt composed of 1-molar amount of PSA and 2-molar amount of (-)-Pro.The salt purified gave (+)-PSA with an optical purity of about 100percent.A salt composed of equimolar amounts of PSA and (-)-Pro was obtained from the ethanolic mother liquor, and gave (-)-PSA with an optical purity of 98percent.

Palladium-Catalyzed Asymmetric Hydroesterification of α-Aryl Acrylic Acids to Chiral Substituted Succinates

A palladium-catalyzed asymmetric hydroesterification of α-aryl acrylic acids with CO and alcohol was developed, preparing a variety of chiral α-substituted succinates in moderate yields with high ee values. The kinetic profile of the reaction progress revealed that the alkene substrate first underwent the hydroesterification followed by esterification with alcohol. The origin of the enantioselectivity was elucidated by density functional theory computation.

An enantioselective claisen rearrangement catalyzed by N-heterocyclic carbenes

In the presence of a chiral azolium salt (10 mol %), enols and ynals undergo a highly enantioselective annulation reaction to form enantiomerically enriched dihydropyranones via an N-heterocyclic carbene catalyzed variant of the Claisen rearrangement. Unlike other azolium-catalyzed reactions, this process requires no added base to generate the putative NHC-catalyst, and our investigations demonstrate that the counterion of the azolium salt plays a key role in the formation of the catalytically active species. Detailed kinetic studies eliminate a potential 1,4-addition as the mechanistic pathway; the observed rate law and activation parameters are consistent with a Claisen rearrangement as the rate-limiting step. This catalytic system was applied to the synthesis of enantioenriched kojic acid derivatives, a reaction of demonstrated synthetic utility for which other methods for catalytic enantioselective Claisen rearrangements have not provided a satisfactory solution.