42771-82-4

Basic information

• Product Name: 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid
• Synonyms: 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid
• CAS NO: 42771-82-4
• Molecular Weight: 288.275
• Mol File: 42771-82-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid(42771-82-4)
• EPA Substance Registry System: 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid(42771-82-4)

Safety Data

• Hazardous Substances Data: 42771-82-4(Hazardous Substances Data)

Usage

Description

2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid is an organic compound that is identified as an impurity in Flurbiprofen (F598700), which is an anti-inflammatory drug commonly used for its analgesic properties. 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid is characterized by its unique molecular structure, which includes a fluorinated biphenyl group and a methylmalonic acid moiety.

Uses

Used in Pharmaceutical Industry:
2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid is used as an impurity in the production of Flurbiprofen, an anti-inflammatory drug. The presence of this compound in the drug is significant as it can affect the drug's efficacy, safety, and quality. It is essential to monitor and control the levels of this impurity during the manufacturing process to ensure the drug meets the required standards.
As an impurity in the pharmaceutical industry, 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid serves as a critical parameter in the quality control and assurance of Flurbiprofen. 2-(2-fluoro-4-biphenylyl)-2-methylmalonic acid's presence can impact the drug's performance, and thus, it is necessary to maintain its levels within acceptable limits to ensure the drug's effectiveness and safety for patients.

Upstream product

• 136434-77-0 4-bromo-3-fluoroiodobenzene 
• 42771-81-3 diethyl 2-(2-fluorobiphenyl-4-yl)-2-methylmalonate 
• 78543-08-5 2-(4-amino-3-fluorophenyl)-2-methylmalonic acid diethyl ester 
• 78543-06-3 diethyl 2-(3-fluoro-4-nitrophenyl)-2-methyl-malonate 
• 446-35-5 2,4-Difluoronitrobenzene 
• 70312-66-2 benzyl 2-(2-fluoro-biphenyl-4-yl)propionate 
• 1020533-77-0 2-fluoro-4-(1,1-difluoroethyl)biphenyl 
• 124-38-9 carbon dioxide 
• 113544-38-0 methyl 2-(2-fluoro-4-biphenylyl)propionate 
• 5104-49-4 fluorobiprofen 
• 543688-88-6 dimethyl 2-(2-fluoro-4-biphenylyl)-2-methylmalonate 

Downstream Products

• 5104-49-4 (S)-(+)-flurbiprofen 
• 5104-49-4 (R)-flurbiprofen 
• 5104-49-4 fluorobiprofen 

Relevant articles and documents

Enzymatic Synthesis of (R)-Flurbiprofen

α-Methyl-α-(2-fluoro-4-biphenylyl)propionic acid (flurbiprofen) was prepared from the corresponding malonic acid derivative via asymmetric decarboxylation catalyzed by an enzyme, arylmalonate decarboxylase (EC 4.1.1.76), in high chemical and optical yields.

Arylmalonate Decarboxylase-Catalyzed Asymmetric Synthesis of Both Enantiomers of Optically Pure Flurbiprofen

The bacterial decarboxylase (AMDase) catalyzes the enantioselective decarboxylation of prochiral arylmalonates with high enantioselectivity. Although this reaction would provide a highly sustainable synthesis of active pharmaceutical compounds such as flurbiprofen or naproxen, competing spontaneous decarboxylation has so far prevented the catalytic application of AMDase. Here, we report on reaction engineering and an alternate protection group strategy for the synthesis of these compounds that successfully suppresses the side reaction and provides pure arylmalonic acids for subsequent enzymatic conversion. Protein engineering increased the activity of the synthesis of the (S)-and (R)-enantiomers of flurbiprofen. These results demonstrated the importance of synergistic effects in the optimization of this decarboxylase. The asymmetric synthesis of both enantiomers in high optical purity (>99 %) and yield (>90 %) can be easily integrated into existing industrial syntheses of flurbiprofen, thus providing a sustainable method for the production of this important pharmaceutical ingredient. Optically pure flurbiprofen: A novel deprotection strategy for the preparation of the starting material combined with decarboxylase (AMDase) variants optimized by enzyme engineering allowed the asymmetric synthesis of both enantiomers of the non-steroidal anti-inflammatory drug (NSAID) flurbiprofen in excellent yield and optical purity.