180293-49-6

Basic information

• Product Name: Benzeneacetic acid, a-fluoro-a-methyl-4-(2-methylpropyl)-
• CAS NO: 180293-49-6
• Molecular Formula: C13H17FO2
• Molecular Weight: 224.275
• Mol File: 180293-49-6.mol
• Article Data: 8

Chemical Properties

• CAS DataBase Reference: Benzeneacetic acid, a-fluoro-a-methyl-4-(2-methylpropyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-fluoro-a-methyl-4-(2-methylpropyl)-(180293-49-6)
• EPA Substance Registry System: Benzeneacetic acid, a-fluoro-a-methyl-4-(2-methylpropyl)-(180293-49-6)

Safety Data

• Hazardous Substances Data: 180293-49-6(Hazardous Substances Data)

Upstream product

• 74590-67-3 ethyl 2-fluoro-2-(4-isobutylphenyl)propanoate 
• 41283-72-1 ibuprofen ethyl ester 
• 918110-09-5 4-isobutyl-α,α-difluoroethylbenzene 
• 124-38-9 carbon dioxide 
• 182816-16-6 2-fluoro-2-(4-isobutylphenyl)propyl acetate 
• 182816-09-7 1-bromo-2-fluoro-2-(4-isobutylphenyl)propane 
• 182816-13-3 1-bromo-2-(4-isobutylphenyl)propan-2-ol 
• 34352-86-8 1-isobutyl-4-(prop-1-en-2-yl)benzene 
• 56374-24-4 (R/S)-4-isobutyl-α-methylstyrene oxide 
• 60473-29-2 ethyl 2-(4-isobutylphenyl)-2-hydroxypropanoate 
• 38861-78-8 1-(4-isobutyl-phenyl)-ethanone 
• 2051-99-2 1-bromo-4-isobutylbenzene 
• 61566-34-5 (+/-)-ibuprofen methyl ester 
• 15687-27-1 ibuprofen 

Downstream Products

• 1394168-98-9 di(naphthalen-1-yl)methyl 2-fluoro-2-(4-isobutylphenyl)propanoate 
• 1394168-88-7 di(naphthalen-1-yl)methyl 2-fluoro-2-(4-isobutylphenyl)propanoate 
• 863224-94-6 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2S)-2-fluoro-2-[4-(2-methylpropyl)phenyl]propionate 
• 863224-93-5 (1R,2R,3R,6S)-4-hydroxy-4,7,7-trimethylbicyclo[4.1.0]hept-3-yl (2R)-2-fluoro-2-[4-(2-methylpropyl)phenyl]propionate 
• 180293-53-2 methyl 2-fluoro-2-[4-(2-methylpropyl)phenyl]propionate 

Relevant articles and documents

Inhibition of human α-methylacyl CoA racemase (AMACR): A target for prostate cancer

The enzyme α-methylacyl CoA racemase (AMACR) is involved in the metabolism of branched-chain fatty acids and has been identified as a promising therapeutic target for prostate cancer. By using the recently available human AMACR from HEK293 kidney cell cultures, we tested a series of new rationally designed inhibitors to determine the structural requirements in the acyl component. An N-methylthiocarbamate (Ki=98nM), designed to mimic the proposed enzyme-bound enolate, was found to be the most potent AMACR inhibitor reported to date. Enolate mimicry: A range of inhibitors were designed and synthesized to determine the structural requirements for inhibition of the prostate cancer target racemase AMACR using the recently available human enzyme from HEK293 kidney cell cultures. An N-methylthiocarbamate (Ki=98nM), designed to mimic the proposed enzyme-bound enolate, is the most potent AMACR inhibitor reported to date.

Electrochemical carboxylation of α,α-difluorotoluene derivatives and its application to the synthesis of α-fluorinated nonsteroidal anti-inflammatory drugs

Electrochemical carboxylation of α,α-difluorotoluene derivatives resulted in an efficient fixation of carbon dioxide to give the corresponding α-fluorophenylacetic acids in good yields, and this reaction was successfully applied to the synthesis of α-fluorinated nonsteroidal anti-inflammatory drugs (NSAIDs). Georg Thieme Verlag Stuttgart.

On the enzymatic hydrolysis of methyl 2-fluoro-2-arylpropionates by lipases

The enzymatic hydrolysis of methyl 2-fluoro-2-arylpropionates was performed using lipases from Candida rugosa and Candida cylindracea (OF-360). A careful analysis of the reaction products revealed that racemic 2-hydroxy-2- arylpropionic acid and traces of 2-arylacrylic acid are formed, in addition to the expected 2-aryl-2-fluoropropionic acid. The presence of powerful electron-releasing groups in the aromatic ring of the substrate increase the amount of 2-hydroxypropionic acid. A mechanistic hypothesis has been formulated according to which the enzyme facilitates the elimination of fluoride ion from the hydrolysed acid with the formation of an α-carboxy-stabilized carbocation which provides 2-hydroxypropionic acids by nucleophilic attack of H2O and 2-arylacrylic acids by a β-elimination process.