(R)-(-)-Phenylsuccinic acid

Base Information

• Chemical Name: (R)-(-)-Phenylsuccinic acid
• CAS No.: 46292-93-7
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: 2917399090
• DSSTox Substance ID: DTXSID70352942
• Nikkaji Number: J84.177C
• Wikidata: Q27460426
• Mol file: 46292-93-7.mol

Synonyms:46292-93-7;(R)-(-)-Phenylsuccinic acid;(R)-2-Phenylsuccinic acid;(2R)-2-phenylbutanedioic acid;(R)-2-Phenyl succinic acid;Butanedioic acid, phenyl-, (2R)-;(2R)-2-phenylbutanedioic acid >99% ee;MFCD00065930;(R)-2-PHENYLSUCCINICACID;r-phenylsuccinic acid;SCHEMBL377609;(R)-2-Phenylbutanedioic acid;(R)-(')-Phenylsuccinic acid;DTXSID70352942;CHEBI:151044;WBA29293;AKOS006239803;SS-4842;BP-12920;CS-0141922;A827021;A1-00043;Q27460426;(R)-(-)-Phenylsuccinic acid, >=96.0% (sum of enantiomers, HPLC)

Chemical Property of (R)-(-)-Phenylsuccinic acid

Chemical Property:

• Appearance/Colour: almost white fine powder
• Vapor Pressure: 0.000306mmHg at 25°C
• Melting Point: 173-176 °C
• Refractive Index: 1.577
• Boiling Point: 307.8 °C at 760mmHg
• PKA: 3.60±0.10(Predicted)
• Flash Point: 154.2 °C
• PSA: 74.60000
• Density: 1.336g/cm³
• LogP: 1.32950
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Acetone (Slightly), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 194.05790880
• Heavy Atom Count: 14
• Complexity: 218

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-(?)-Phenylsuccinic acid ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(CC(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@@H](CC(=O)O)C(=O)O
• Uses: (R)-Phenylsuccinic Acid is an intermediate used in the preparation of optically active succinic acid derivatives used as hypoglycemic agents.

Technology Process of (R)-(-)-Phenylsuccinic acid

There total 3 articles about (R)-(-)-Phenylsuccinic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

2-phenylsuccinic acid (635-51-8,10424-29-0) → (S)-2-phenylsuccinic acid (4036-30-0) + R-(+)-phenylsuccinic acid (46292-93-7)

Guidance literature:

With sodium hydroxide; thionyl chloride; brucine; Product distribution; multistep reaction; 2.) 100 deg C; the ratio of the racemization;

DOI:10.1002/hlca.19820650135

Reference yield:

(R)-(-)-dimethyl 2-phenylsuccinate (114030-75-0) → R-(+)-phenylsuccinic acid (46292-93-7)

Guidance literature:

With sodium hydroxide; In methanol; water; for 1h; Heating;

DOI:10.1021/ja00293a038

Reference yield:

2-phenylsuccinic acid (635-51-8,10424-29-0) → R-(+)-phenylsuccinic acid (46292-93-7)

Guidance literature:

With brucine;

upstream raw materials:

2-phenylsuccinic acid

(R)-(-)-dimethyl 2-phenylsuccinate

Downstream raw materials:

(2R)-2-phenylbutane-1,4-diol

(2R)-2-cyclohexylsuccinic acid

(R)-2,3-dihydro-1H-indene-1-carboxylic acid

(S)-2,3-dihydro-1H-indene-1-carboxylic acid

Refernces

• 1、 Meng, Huiwen,Yan, Tao,Jiao, Feipeng,Wang, Shuai. "Enantioseparation of Phenylsuccinic Acid Enantiomers by Solvent Sublation with Collaborative Selectors". . p. 2159 - 2170. Retrieved 2017/11/22.
• 2、 Brunner, H.,Zettlmeier, W.. "ENANTIOSELEKTIVE KATALYSE, 63 - OPTISCH AKTIVE PHOSPHINE AUS DICARBONSAEUREN UND IHR EINSATZ IN DER ENANTIOSELEKTIVEN HYDRIERUNG". . p. 259 - 265. Retrieved 2007/10/02.