(S)-(+)-Phenylsuccinic acid

Base Information

• Chemical Name: (S)-(+)-Phenylsuccinic acid
• CAS No.: 4036-30-0
• Molecular Formula: C10H10O4
• Molecular Weight: 194.187
• Hs Code.: 29171990
• European Community (EC) Number: 223-719-3
• Nikkaji Number: J1.249.844F
• Wikidata: Q27460184
• Mol file: 4036-30-0.mol

Synonyms:4036-30-0;(S)-(+)-Phenylsuccinic acid;(S)-2-phenylsuccinic acid;(2S)-2-phenylbutanedioic acid;(S)-2-Phenyl succinic acid;Butanedioic acid, phenyl-, (2S)-;(2S)-2-phenylbutanedioic acid >99% ee;(S)-Phenylsuccinic acid;(S)-2-Phenylsuccinicacid;EINECS 223-719-3;SCHEMBL377175;QSPL 009;MFCD00065929;AKOS015840414;CS-W010661;SS-4844;P0936;Q27460184;(S)-(+)-Phenylsuccinic acid, >=99.0% (sum of enantiomers, HPLC);inverted exclamation mark(2)R inverted exclamation mark(3)-(+)-Phenylsuccinic acid

Chemical Property of (S)-(+)-Phenylsuccinic acid

Chemical Property:

• Appearance/Colour: almost white micro-crystalline powder
• Vapor Pressure: 0.000306mmHg at 25°C
• Melting Point: 173-176 °C
• Refractive Index: 147.5 ° (C=2, EtOH)
• Boiling Point: 307.8 °C at 760 mmHg
• PKA: 3.60±0.10(Predicted)
• Flash Point: 154.2 °C
• PSA: 74.60000
• Density: 1.337 g/cm³
• LogP: 1.32950
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: within almost transparency in Methanol
• 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% ^*data from raw suppliers

(S)-(+)-Phenylsuccinic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 22-24/25-37/39-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

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

Technology Process of (S)-(+)-Phenylsuccinic acid

There total 10 articles about (S)-(+)-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: 90.0%

4-hydroxy-3-phenylbutyro-1,4-lactone (78920-22-6) → (S)-2-phenylsuccinic acid (4036-30-0)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; In water; acetone; ice-cooling;

DOI:10.1039/P19830002629

Reference yield: 55.0%

carbon monoxide (201230-82-2) + 2-phenylacrylic acid (492-38-6) → (S)-2-phenylsuccinic acid (4036-30-0)

Guidance literature:

With (S)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(diphenylphosphine); water; palladium(II) acetylacetonate; toluene-4-sulfonic acid; In 1,2-dichloro-ethane; at 60 ℃; for 48h; enantioselective reaction; Autoclave;

DOI:10.1021/acs.orglett.1c03361

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

upstream raw materials:

2-phenylsuccinic acid

4-hydroxy-3-phenylbutyro-1,4-lactone

2,3-dideoxy-3C-phenyl-D-manno-heptono-1,4-lactone

(S)-methyl-3-(6-((tert-butyldimethylsilyloxy)methyl)-3-hydroxy-4-oxo-4H-pyran-2-yl)-3-phenylpropanoate

Downstream raw materials:

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

methanesulfonic acid (S)-4-methanesulfonyloxy-3-phenyl-butyl ester

(S)-3-(4-nitro-phenyl)-1-propyl-pyrrolidine

(S)-3-(4-amino-phenyl)-1-propyl-pyrrolidine

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.
• 2、 Tang, Bo,Sun, Chenyu,Wang, Wei,Geng, Lina,Sun, Liquan,Luo, Aiqin. "Chiral amorphous metal–organic polyhedra used as the stationary phase for high-resolution gas chromatography separations". . p. 1178 - 1185. Retrieved 2020/07/09.