Fenoprofen

Base Information

• Chemical Name: Fenoprofen
• CAS No.: 29679-58-1
• Deprecated CAS: 31879-05-7
• Molecular Formula: C15H14O3
• Molecular Weight: 242.274
• Hs Code.: 2918999090
• European Community (EC) Number: 249-770-1,250-850-3,252-107-9,672-650-9
• NSC Number: 757813
• UNII: RA33EAC7KY
• DSSTox Substance ID: DTXSID9023045
• Nikkaji Number: J286.928D
• Wikipedia: Fenoprofen
• Wikidata: Q2555245
• NCI Thesaurus Code: C61760
• RXCUI: 4331
• Pharos Ligand ID: 1RAP3GY7FW3S
• Metabolomics Workbench ID: 42906
• ChEMBL ID: CHEMBL1297
• Mol file: 29679-58-1.mol

Synonyms:Fenoprofen;Fenoprofen Calcium;Fenoprofen Dihydrate, Calcium Salt;Fenoprofen, Anhydrous, Calcium Salt;Nalfon;Nalgesic

Chemical Property of Fenoprofen

Chemical Property:

• Vapor Pressure: 1.71E-06mmHg at 25°C
• Refractive Index: 1.583
• Boiling Point: 381.3 °C at 760 mmHg
• PKA: 4.20±0.10(Predicted)
• Flash Point: 141.7 °C
• PSA: 46.53000
• Density: 1.183 g/cm³
• LogP: 3.66700
• XLogP3: 3.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 242.094294304
• Heavy Atom Count: 18
• Complexity: 271

Purity/Quality:

99%, ^*data from raw suppliers

Fenoprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Nonsteroidal Antiinflammatory Drugs
• Canonical SMILES: CC(C1=CC(=CC=C1)OC2=CC=CC=C2)C(=O)O
• Uses: Fenoprofen is a positive allosteric modulators at melanocortin receptor 3 for treatment of inflammatory diseases in human and mouse model.

Technology Process of Fenoprofen

There total 31 articles about Fenoprofen 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: 97.0%

α-methylthio-α-(m-phenoxyphenyl)propionic acid (64782-40-7) → Fenoprofen (29679-58-1,31879-05-7,32953-79-0)

Guidance literature:

In tetrahydrofuran; ethanol; water; tert-butyl alcohol;

Reference yield: 97.0%

2-(3-phenoxy-phenyl)-propan-1-ol (32929-75-2) → Fenoprofen (29679-58-1,31879-05-7,32953-79-0)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium chlorite; In water; acetonitrile; at 35 ℃; for 24h; aq. phosphate buffer;

DOI:10.1055/s-0030-1258580

Reference yield: 94.0%

3-bromodiphenyl ether (6876-00-2) + 1,1-bis(trimethylsilyloxy)prop-1-ene (31469-22-4) → Fenoprofen (29679-58-1,31879-05-7,32953-79-0)

Guidance literature:

3-bromodiphenyl ether; With zinc(II) fluoride; tri-tert-butyl phosphine; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In toluene; for 0.666667h; Inert atmosphere;

1,1-bis(trimethylsilyloxy)prop-1-ene; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; at 80 ℃; for 12h; Sealed tube; Inert atmosphere;

DOI:10.1021/jacs.9b03291

upstream raw materials:

carbon dioxide

1-(m-phenoxyphenyl)-1-chloroethane

methyl 2-(3-phenoxybenzene)propionate

1,1-bis(trimethylsilyloxy)prop-1-ene

Downstream raw materials:

N-cyclopropylmethyl-2-(3-phenoxyphenyl)propionamide

(R)-fenoprofen di(1-naphthyl)methyl ester

(S)-fenoprofen

(R)-fenoprofen

Refernces

• 1、 Gevorgyan, Ashot,Hopmann, Kathrin H.,Bayer, Annette. "Exploration of New Biomass-Derived Solvents: Application to Carboxylation Reactions". . p. 2080 - 2088. Retrieved 2020/02/20.
• 2、 Meng, Qing-Yuan,Schirmer, Tobias E.,Berger, Anna Lucia,Donabauer, Karsten,K?nig, Burkhard. "Photocarboxylation of Benzylic C-H Bonds". supporting information. p. 11393 - 11397. Retrieved 2019/08/20.