2-(2-Fluorobiphenyl-4-yl)-2,3-dimethylbutanedioic acid

Base Information

• Chemical Name: 2-(2-Fluorobiphenyl-4-yl)-2,3-dimethylbutanedioic acid
• CAS No.: 42771-82-4
• Molecular Formula: C₁₆H₁₃FO₄
• Molecular Weight: 288.275
• UNII: J2NQT8L06Q
• DSSTox Substance ID: DTXSID60195426
• Wikidata: Q27281065
• Mol file: 42771-82-4.mol

Synonyms:42771-82-4;2-(2-Fluorobiphenyl-4-yl)-2,3-dimethylbutanedioic acid;UNII-J2NQT8L06Q;J2NQT8L06Q;Flurbiprofen Related Impurity 2;2-(3-fluoro-4-phenylphenyl)-2-methylpropanedioic acid;SCHEMBL10704177;DTXSID60195426;AHAWBBIKBPNXOF-UHFFFAOYSA-N;SY348303;2-(2-Fluoro-4-biphenylyl)-2-methylmalonic Acid;2-(2-fluoro-4-biphenylyl)-2-methyl malonic acid;Q27281065;2-(2-Fluoro-[1,1'-biphenyl]-4-yl)-2-methylmalonic acid;Propanedioic acid, (2-fluoro[1,1'-biphenyl]-4-yl)methyl-;2-(2-Fluoro[1,1'-biphenyl]-4-yl)-2-methylpropanedioic acid

Chemical Property of 2-(2-Fluorobiphenyl-4-yl)-2,3-dimethylbutanedioic acid

Chemical Property:

• XLogP3: 3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 288.07978705
• Heavy Atom Count: 21
• Complexity: 389

Purity/Quality:

98% ^*data from raw suppliers

2-(2-Fluoro-[1,1''-biphenyl]-4-yl)-2-methylmalonicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C1=CC(=C(C=C1)C2=CC=CC=C2)F)(C(=O)O)C(=O)O
• Uses: 2-(2-Fluoro-[1,1''-biphenyl]-4-yl)-2-methylmalonic Acid is an impurity of Flurbiprofen (F598700), an anti-inflammatory used as an analgesic.

Technology Process of 2-(2-Fluorobiphenyl-4-yl)-2,3-dimethylbutanedioic acid

There total 15 articles about 2-(2-Fluorobiphenyl-4-yl)-2,3-dimethylbutanedioic 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: 85.0%

dimethyl 2-(2-fluoro-4-biphenylyl)-2-methylmalonate (543688-88-6) → 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid (42771-82-4)

Guidance literature:

With potassium hydroxide; In ethanol; water; at 0 ℃; for 1h;

DOI:10.1246/bcsj.76.2395

Reference yield: 74.0%

2-fluoro-4-(1,1-difluoroethyl)biphenyl (1020533-77-0) + carbon dioxide (124-38-9,18923-20-1) → 2-fluoro-2-(3-fluoro-4-phenylphenyl)propionic acid (863224-90-2) + 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid (42771-82-4)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In N,N-dimethyl-formamide; at -20 ℃; Electrolysis;

DOI:10.1055/s-2008-1032069

Reference yield: 58.0%

dibenzyl 2-(2-fluoro-[1,1’-biphenyl]-4-yl)-2-methylmalonate → 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid (42771-82-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tert-butyl methyl ether; at 0 ℃; for 5h;

DOI:10.1002/cctc.201501205

upstream raw materials:

dimethyl 2-(2-fluoro-4-biphenylyl)-2-methylmalonate

fluorobiprofen

methyl 2-(2-fluoro-4-biphenylyl)propionate

2-fluoro-4-(1,1-difluoroethyl)biphenyl

Downstream raw materials:

(S)-(+)-flurbiprofen

(R)-flurbiprofen

fluorobiprofen