(S,S)-2,3-Diphenylsuccinic acid

Base Information

• Chemical Name: (S,S)-2,3-Diphenylsuccinic acid
• CAS No.: 74431-38-2
• Molecular Formula: C16H14 O4
• Molecular Weight: 270.285
• Hs Code.: 2917399090
• DSSTox Substance ID: DTXSID70353530
• Nikkaji Number: J989.973A
• Wikidata: Q82131180
• Mol file: 74431-38-2.mol

Synonyms:74431-38-2;(S,S)-2,3-DIPHENYLSUCCINIC ACID;(2S,3S)-2,3-diphenylbutanedioic acid;(2S,3S)-2,3-Diphenylsuccinic acid;Butanedioic acid,2,3-diphenyl-, (2S,3S)-;(R,R)-2,3-DIPHENYLSUCCINIC ACID;SCHEMBL7815004;DTXSID70353530;21037-34-3;AG-G-95959;(S,S)-(+)-2,3-DIPHENYLSUCCINIC ACID;methyl 3-amino-5-(1-benzyl-3-methyl-1H-pyrazol-4-yl)thiophene-2-carboxylate

Chemical Property of (S,S)-2,3-Diphenylsuccinic acid

Chemical Property:

• Melting Point: 250 - 252 °C
• PSA: 74.60000
• LogP: 2.72320
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 270.08920892
• Heavy Atom Count: 20
• Complexity: 306

Purity/Quality:

99.3% ^*data from raw suppliers

(2S,3S)-2,3-DiphenylsuccinicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(C2=CC=CC=C2)C(=O)O)C(=O)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H]([C@@H](C2=CC=CC=C2)C(=O)O)C(=O)O
• Uses: (2S,3S)-2,3-Diphenylsuccinic Acid is a reagent for stereoselective hydrocoupling of optically active cinnamoyloxazolidinones by electroreduction.

Technology Process of (S,S)-2,3-Diphenylsuccinic acid

There total 119 articles about (S,S)-2,3-Diphenylsuccinic 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:

sodium phenylacetate (114-70-5) → meso-2,3-diphenylsuccinic acid (7584-72-7,21037-34-3,41915-64-4,47039-46-3,74431-38-2,1225-13-4) + MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With diethyl ether; isopropylmagnesium bromide; anschliessend Behandeln mit Sauerstoff;

Reference yield:

isopropylmagnesium bromide (920-39-8) + sodium phenylacetate (114-70-5) → 2-bromophenylacetic acid (4870-65-9,31302-84-8) + meso-2,3-diphenylsuccinic acid (7584-72-7,21037-34-3,41915-64-4,47039-46-3,74431-38-2,1225-13-4)

Guidance literature:

With bromine;

Reference yield:

hydrogenchloride (7647-01-0,15364-23-5) + 3-(4-dimethylamino-phenylimino)-4,5-diphenyl-cyclopentane-1,2-dione → meso-2,3-diphenylsuccinic acid (7584-72-7,21037-34-3,41915-64-4,47039-46-3,74431-38-2,1225-13-4) + 4-amino-N,N-dimethylaniline (99-98-9)

Guidance literature:

at 130 - 140 ℃;

upstream raw materials:

2-bromophenylacetic acid

(E)-1,2-diphenyl-ethene

diethyl ether

bibenzyl-α,α'-diyl dipotassium

Downstream raw materials:

3,4-diphenyl-1-propyl-pyrrolidine-2,5-dione

meso-2,3-diphenyl-succinic acid monoethyl ester

1-(1-methyl-pentyl)-3,4-diphenyl-pyrrolidine-2,5-dione

(2R₃R)-2,3-Diphenylbernsteinsaeure

Refernces

• 1、 Claveau, Romain,Twamley, Brendan,Connon, Stephen J.. "Dynamic kinetic resolution of bis-aryl succinic anhydrides: Enantioselective synthesis of densely functionalised γ-butyrolactones". . p. 3231 - 3234. Retrieved 2018/04/05.
• 2、 Rao, Vutukuri Dharma,Periasamy, Mariappan. "Convenient synthetic methods to C2 symmetric 3,4-diphenylpyrrolidines". . p. 703 - 706. Retrieved 2007/10/03.