46292-93-7

Basic information

• Product Name: (R)-(-)-Phenylsuccinic acid
• Synonyms: (R)2-Phenylsuccinicacid;(R)-(-)-PHENYLSUCCINIC ACID;(R)-(-)-PHENYLSUCCINIC ACID 99+%;(R)-2-Phenylbutanedioic acid;Butanedioic acid, 2-phenyl-, (2R)-;(R)-(-)-Phenylsuccinic acid >=96.0% (sum of enantiomers, HPLC);(2R)-2-Phenylbutanedioic acid;(2R)-2-Phenylbutanedioicacid>99%ee
• CAS NO: 46292-93-7
• Molecular Formula: C₁₀H₁₀O₄
• Molecular Weight: 194.18
• Product Categories: Miscellaneous;Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 46292-93-7.mol
• Article Data: 7

Chemical Properties

• Melting Point: 173-176 °C
• Boiling Point: 290.62°C (rough estimate)
• Flash Point: 154.2 °C
• Appearance: almost white fine powder
• Density: 1.2534 (rough estimate)
• Vapor Pressure: 0.000306mmHg at 25°C
• Refractive Index: 1.5430 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Acetone (Slightly), Methanol (Slightly)
• PKA: 3.60±0.10(Predicted)
• BRN: 3201702
• CAS DataBase Reference: (R)-(-)-Phenylsuccinic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-(-)-Phenylsuccinic acid(46292-93-7)
• EPA Substance Registry System: (R)-(-)-Phenylsuccinic acid(46292-93-7)

Safety Data

• Safety Statements: 22-24/25
• WGK Germany: 3
• Hazardous Substances Data: 46292-93-7(Hazardous Substances Data)

Usage

Chemical Properties

almost white fine powder

Uses

(R)-Phenylsuccinic Acid is an intermediate used in the preparation of optically active succinic acid derivatives used as hypoglycemic agents.

Purification Methods

Purify the acids by re-precipitation from alkali and recrystallisation from H2O. [Naps & Johns J Am Chem Soc 62 2450 1940, Fredga & Matell Bull Soc Chim Belg 62 47 1953, Wren & Williams J Chem Soc 109 572 1916.] The racemate [635-51-8] has m 166-168o, 168o after recrystallisation from H2O or MeCN. Its S-benzylisothiuronium salt has m 164-165o (from EtOH) [Griediger & Pedersen Acta Chem Scand 9 1425 1955]. [Beilstein 9 IV 3351.]

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-/m1/s1

Upstream product

• 635-51-8 2-phenylsuccinic acid 
• 114030-75-0 (R)-(-)-dimethyl 2-phenylsuccinate 

Downstream Products

• 95840-73-6 (2R)-2-phenylbutane-1,4-diol 
• 136570-32-6 (2R)-2-cyclohexylsuccinic acid 
• 877-01-0 (R)-2,3-dihydro-1H-indene-1-carboxylic acid 
• 68000-22-6 (S)-2,3-dihydro-1H-indene-1-carboxylic acid 

Relevant articles and documents

Chiral amorphous metal–organic polyhedra used as the stationary phase for high-resolution gas chromatography separations

Herein, we describe a new chiral amorphous metal–organic polyhedra used as the stationary phase for high-resolution gas chromatography (GC). The chiral stationary phase was coated onto a capillary column via a dynamic coating process and investigated for a variety of compounds. The experimental results showed that the chiral stationary phase exhibits good selectivity for linear alkanes, linear alcohols, polycyclic aromatic hydrocarbons, isomers, and chiral compounds. In addition, the column has the advantages of high column efficiency and short analysis time. The present work indicated that amorphous metal–organic polyhedra have great potential for application as a new type of stationary phase for GC.

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.

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.