Flurbiprofen methyl ester

Base Information

• Chemical Name: Flurbiprofen methyl ester
• CAS No.: 66202-86-6
• Molecular Formula: C₁₆H₁₅FO₂
• Molecular Weight: 258.292
• European Community (EC) Number: 889-721-7
• DSSTox Substance ID: DTXSID50274416
• Nikkaji Number: J1.188.598E
• ChEMBL ID: CHEMBL162300
• Mol file: 66202-86-6.mol

Synonyms:Flurbiprofen methyl ester;66202-86-6;[1,1'-Biphenyl]-4-acetic acid, 2-fluoro-a-methyl-, methyl ester;methyl flurbiprofen;methyl 2-(3-fluoro-4-phenylphenyl)propanoate;MethylFlurbiprofen-d3;CHEMBL162300;METHYL 2-(2-FLUORO-BIPHENYL-4-YL)-PROPIONATE;methyl 2-(2-fluoro-biphenyl-4yl)propionate;Methyl 2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate;methyl 2-{2-fluoro-[1,1'-biphenyl]-4-yl}propanoate;methyl 2-(2-fluorobiphenyl-4-yl)propanoate;SCHEMBL1543413;SCHEMBL13448835;DTXSID50274416;BDBM50139246;AKOS016035422;BS-18953;methyl 2-(2-fluorobiphenyl-4yl)propanoate;methyl 2-(2-fluoro-4-biphenylyl)propionate;FT-0671786;Methyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)propanoate;Methyl2-(2-fluoro-[1,1'-biphenyl]-4-yl)propanoate;2-(2-Fluoro-biphenyl-4-yl)-propionic acid methyl ester;Methyl 2-(2-fluoro[1,1'-biphenyl]-4-yl)propanoate #;Methyl flurbiprofen;2-Fluoro-alpha-methyl-[1,1'-biphenyl]-4-acetic acid methyl ester;(+/-)-Flubiprofen methyl ester

Chemical Property of Flurbiprofen methyl ester

Chemical Property:

• Vapor Pressure: 0.000106mmHg at 25°C
• Melting Point: 39-40oC
• Boiling Point: 337.3oC at 760 mmHg
• Flash Point: 152.6oC
• PSA: 26.30000
• Density: 1.127g/cm3
• LogP: 3.76920
• Storage Temp.: Refrigerator
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 258.10560788
• Heavy Atom Count: 19
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

MethylFlurbiprofen ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)C(=O)OC
• Uses: Methyl Flurbiprofen is the prodrug of flurbiprofen. An intermediate for the synthesis of the metabolite of Flurbiprofen, an anti-inflammatory used as an analgesic.

Technology Process of Flurbiprofen methyl ester

There total 3 articles about Flurbiprofen methyl ester 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: 56.0%

C12H16FNO5S (1201594-47-9) + phenylboronic acid (98-80-6) → fluorobiprofen (5104-49-4) + methyl 2-(2-fluoro-4-biphenylyl)propionate (113544-38-0,113544-39-1,114376-61-3,66202-86-6)

Guidance literature:

With potassium phosphate; bis(tricyclohexylphosphine)nickel(II) dichloride; In toluene; at 130 ℃; for 24h; Inert atmosphere;

DOI:10.1021/ja906477r

Reference yield:

methanol (67-56-1) + fluorobiprofen (5104-49-4) → (S)-(+)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9) + (R)-flurbiprofen (5104-49-4,51543-38-5,51543-39-6,51543-40-9) + methyl 2-(2-fluoro-biphenyl-4-yl)propionate (113544-39-1) + methyl 2-(2-fluoro-biphenyl-4-yl)propionate (66202-86-6,113544-39-1,114376-61-3,113544-38-0)

Guidance literature:

In acetonitrile; at 45 ℃; for 48h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; immobilized lipase from Candida antarctica (Novozym 435);

DOI:10.1016/0957-4166(95)00223-C

Reference yield:

methanol (67-56-1) + (R)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose (113544-32-4,113544-33-5) → 1,2-O-isopropylidene-α-D-gluco-/β-L-idofuranose (253328-56-2) + methyl 2-(2-fluoro-biphenyl-4-yl)propionate (66202-86-6,113544-39-1,114376-61-3,113544-38-0)

Guidance literature:

With potassium carbonate; at 20 ℃;

upstream raw materials:

methanol

(R)-3-O-(2-(2-fluoro-4-biphenyl)propionyl)-1,2-O-isopropylidene-α-D-glucofuranose

fluorobiprofen

C₁₂H₁₆FNO₅S

Downstream raw materials:

fluorobiprofen

4-{2'-fluoro-4'-[1-oxo-1-(3-(1,2,3,4-tetrahydroacridin-9-ylamino)propylamino)propan-2-yl]biphenyl-4-yloxy}butyl nitrate

6-{2'-fluoro-4'-[1-oxo-1-(3-(1,2,3,4-tetrahydroacridin-9-ylamino)propylamino)propan-2-yl]biphenyl-4-yloxy}hexyl nitrate

2-{2'-fluoro-4'-[1-oxo-1-(4-(1,2,3,4-tetrahydroacridin-9-ylamino)butylamino)propan-2-yl]biphenyl-4-yloxy}ethyl nitrate

Refernces

• 1、 Morrone,Nicolosi,Patti,Piattelli. "Resolution of racemic flurbiprofen by lipase-mediated esterification in organic solvent". . p. 1773 - 1778. Retrieved 2007/10/02.