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

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

Uses

Used in Pharmaceutical Industry:
(R)-(-)-Phenylsuccinic acid is used as an intermediate in the synthesis of optically active succinic acid derivatives, which serve as hypoglycemic agents. These agents are crucial in the development of medications for the treatment of diabetes, helping to regulate blood sugar levels and improve the quality of life for patients.

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

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

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.

Enantioseparation of Phenylsuccinic Acid Enantiomers by Solvent Sublation with Collaborative Selectors

A new solvent sublation (SS) system for chiral separation is introduced by using phenylsuccinic acid (H2A) as the model enantiomers. The experiments were carried out in a traditional SS apparatus but with collaborative chiral selectors: dibenzoyl-L-tartaric acid (L-DBTA) in the organic phase and hydroxypropyl-β-cyclodextrin (HP-β-CD) in the aqueous phase. The chiral recognition abilities of the two selectors are opposite for the H2A enantiomers. Several important parameters were investigated. The results demonstrate that enantioselective sublation and partitioning behavior are mainly dependent on the pH of the solution, the concentrations of chiral selectors and H2A. Furthermore, the flow rate of air and flotation time also have some effects on the enantioseparation. Under the optimized conditions, the enantioselectivity expressed by the separation factor (β) and enantiomer excess (e.e.%) are 2.47 and 29.50%, and the yields of R-H2A and S-H2A are 0.23 and 0.13?g·L?1, respectively. Compared with the SS system with the single selector HP-β-CD in the aqueous phase (or L-DBTA in the organic phase), the increased values of β and e.e.% in the new SS system with collaborative selectors are 1.31 (or 1.38) and 5.90% (or 13.82%), respectively.

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.

ENANTIOSELEKTIVE KATALYSE, 63 - OPTISCH AKTIVE PHOSPHINE AUS DICARBONSAEUREN UND IHR EINSATZ IN DER ENANTIOSELEKTIVEN HYDRIERUNG

Two optically active bident phosphine ligands were synthesized from derivatives of succinic acid as starting materials.The optical resolution of the acids was carried out with cinchonidine and (S)-α-phenylethylamine.In the Rh-catalyzed enantioselective hydrogenation of α-acetamidocinnamic acid, the bisphosphine with a phenyl substituent in the 2-position of the four-carbon chain gave enantiomeric excess of 17percent.The enantiomeric excess was twice as high with the corresponding thienyl substituted biphosphine.

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.

Asymmetric Synthesis. Asymmetric Catalytic Allylation Using Palladium Chiral Phosphine Complexes

The general characteristics of asymmetric catalytic allylation are analyzed in terms of the properties of the allyl acetate substrates and of the putative (?-allyl)palladium(II) intermediates.After examining the diastereometric equilibria of a series of + complexes, it was established that anti-disposed ?-allyl substituents are the major source of discrimination and that aryl substituents cause an enhancement of the epimerization rate and also are responsible for the greatest discrimination.The ?-allyl substituents appear to contribute additively to the discrimination, and a sector rule is proposed for predicting diastereomeric equilibrium constants.Under appropriate conditions, it is proposed that the optical yields of asymmetric catalytic allylation can be predicted from the chiral discrimination found for these ?-allyl intermediates.These proposals were tested and optical yields of up to 86percent are reported.Quantitative chemical yields were obtained, catalysis can be performed at 25 degC, and the products are readily transformed into useful chirons.The optical yields are sensitive to the chiral phosphine used but are insensitive to the nature of the nucleophiles that were used.There is an approximate correlation of the optical yield with the previously observed diastereomeric ratio of the corresponding (?-allyl)palladium intermediate.All of the reactions are completely regioselective, and all of the nucleophiles used gave the same prevailing enantiomer of the product for a given chiral phosphine.

On the Absolute Configuration of (+)-Indane-1-carboxylic Acid

The (R)-configuration, attributed to (+)-indane-carboxylic acid ((+)-1) by Fredga, is unequivocally confirmed (Scheme 1).Configurational doubts, raised by an erroneous ORD. curve of (-)-1-methylindane ((-)-4) published by Brewster and Buta, are unfounded (cf. the following paper of Brewster and the corrections in ).This was further verified by preparing deuteriated 1-methylindanes starting with (-)-(R)-3-phenylbutyric acid ((-)-(R)-5) as well as with (+)-(R)-1 or (-)-(S)-1 (Scheme 2).The ORD. curves of the optically active 4 thus obtained were (disregarding deuterium isotope effects) identical or antipodal, respectively (cf.Fig.1,2, and 7a-e).Optically active methyl indane-1-carboxylates ((-)-(R)-14 or (+)-(S)--14) show a strong solvent dependence of their ORD. and CD. spectra with a sign inversion occuring in going from isooctane to methanol or benzene.The observed changes can be explained by a change in the population of comformations where the ester carbonyl group is eclipsed either with the C(1),C(2)- or C(1),H-bond, with the n,?*-transition having a slightly different energy and the ester group an essentially enantiomeric environment with respect to its orientation relative to the benzene moiety.