(R)-Suprofen

Base Information

• Chemical Name: (R)-Suprofen
• CAS No.: 52780-13-9
• Deprecated CAS: 77981-82-9
• Molecular Formula: C8H8O3S
• Molecular Weight: 260.313
• European Community (EC) Number: 258-176-1
• UNII: W67A3375VW
• DSSTox Substance ID: DTXSID501317968
• Nikkaji Number: J295.797C
• Wikidata: Q27292382
• Pharos Ligand ID: S1A6FFQNLXHB
• ChEMBL ID: CHEMBL253765
• Mol file: 52780-13-9.mol

Synonyms:(R)-Suprofen;Suprofen, (R)-;52780-13-9;UNII-W67A3375VW;W67A3375VW;EINECS 258-176-1;Benzeneacetic acid, alpha-methyl-4-(2-thienylcarbonyl)-, (R)-;(R)-(Thien-2-ylcarbonyl)propionic acid;C14H12O3S;(-)-alpha-Methyl-4-(2-thienylcarbonyl)benzeneacetic acid;NCGC00016846-01;CAS-40828-46-4;(-)-SUPROFEN;CHEMBL253765;SCHEMBL1122667;(2R)-2-[4-(thiophene-2-carbonyl)phenyl]propanoic acid;DTXSID501317968;LS-28962;EN300-23857793;(R)-2-[4-(2-thienylcarbonyl)phenyl]propanoic acid;Q27292382;(.ALPHA.R)-.ALPHA.-METHYL-4-(2-THIENYLCARBONYL)BENZENEACETIC ACID;BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-THIENYLCARBONYL)-, (R)-;BENZENEACETIC ACID, .ALPHA.-METHYL-4-(2-THIENYLCARBONYL)-, (.ALPHA.R)-;77981-82-9

Chemical Property of (R)-Suprofen

Chemical Property:

• Refractive Index: 1.612
• Boiling Point: 442.6°Cat760mmHg
• Flash Point: 221.5°C
• PSA: 82.61000
• Density: 1.29g/cm³
• LogP: 3.16720
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 260.05071541
• Heavy Atom Count: 18
• Complexity: 321

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC=C(C=C1)C(=O)C2=CC=CS2)C(=O)O
• Isomeric SMILES: C[C@H](C1=CC=C(C=C1)C(=O)C2=CC=CS2)C(=O)O

Technology Process of (R)-Suprofen

There total 12 articles about (R)-Suprofen 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-[4-(thien-2-ylcarbonyl)phenyl]propanoic acid (40828-46-4) → (R)-Suprofen (52780-13-9)

Guidance literature:

With methanol; C_. antarctica lipase-silicone composite; In dichloromethane; at 40 ℃; for 40h;

DOI:10.1021/ja9924849

Reference yield:

2-[4-(thien-2-ylcarbonyl)phenyl]propanoic acid (40828-46-4) → (S)-Suprofen (52780-12-8) + (R)-Suprofen (52780-13-9)

Guidance literature:

With trifluoroacetic acid; In methanol; at 35 ℃; under 103432 Torr; Reagent/catalyst; Solvent; Resolution of racemate; Supercritical conditions;

DOI:10.1002/chir.22701

Reference yield:

α-methyl-4-(2-thienylcarbonyl)benzeneacetyl chloride (52780-20-8) → (R)-Suprofen (52780-13-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / Et₃N / CH₂Cl₂ / 3 h / 0 °C

2: 2 N HCl, AcOH / 2.5 h / Heating

With hydrogenchloride; acetic acid; triethylamine; In dichloromethane;

DOI:10.1016/0957-4166(95)00110-B

upstream raw materials:

(S)-2-[4-(2-Thiophen-2-yl-[1,3]dioxolan-2-yl)-phenyl]-propionic acid 2'-hydroxy-[1,1']binaphthalenyl-2-yl ester

2-[4-(thien-2-ylcarbonyl)phenyl]propanoic acid

α-methyl-4-(2-thienylcarbonyl)benzeneacetyl chloride

thiophene-2-carbaldehyde

Refernces

• 1、 Gill, Iqbal,Pastor, Eitel,Ballesteros, Antonio. "Lipase-silicone biocomposites: Efficient and versatile immobilized biocatalysts". . p. 9487 - 9496. Retrieved 2007/10/03.
• 2、 Fuji,Node,Tanaka. "Complex-induced proximity effects in enolate formation. Highly diastereoselective α-methylation of binaphthyl esters of arylacetic acids". . p. 6553 - 6556. Retrieved 2007/10/02.