Fluoro ibuprofen

Base Information

• Chemical Name: Fluoro ibuprofen
• CAS No.: 180293-49-6
• Molecular Formula: C13H17FO2
• Molecular Weight: 224.275
• DSSTox Substance ID: DTXSID901208737
• Nikkaji Number: J1.482.566E
• Mol file: 180293-49-6.mol

Synonyms:fluoro ibuprofen;DTXSID901208737;180293-49-6;alpha-Fluoro-alpha-methyl-4-(2-methylpropyl)benzeneacetic acid

Chemical Property of Fluoro ibuprofen

Chemical Property:

• XLogP3: 3.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 224.12125794
• Heavy Atom Count: 16
• Complexity: 244

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)CC1=CC=C(C=C1)C(C)(C(=O)O)F

Technology Process of Fluoro ibuprofen

There total 18 articles about Fluoro ibuprofen 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: 100.0%

methyl 2-fluoro-2-[4-(2-methylpropyl)phenyl]propionate (180293-53-2,180293-55-4) → 2-fluoro-2-[4-(2-methylpropyl)phenyl]propionic acid (180293-49-6)

Guidance literature:

With potassium hydroxide; In methanol; at 20 ℃;

DOI:10.1248/cpb.53.524

Reference yield: 82.0%

4-isobutyl-α,α-difluoroethylbenzene (918110-09-5) + carbon dioxide (124-38-9,18923-20-1) → 2-fluoro-2-[4-(2-methylpropyl)phenyl]propionic acid (180293-49-6)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; In N,N-dimethyl-formamide; at 0 ℃; Electrolysis;

DOI:10.1055/s-2008-1032069

Reference yield: 70.0%

ethyl 2-fluoro-2-(4-isobutylphenyl)propanoate (74590-67-3) → 2-fluoro-2-[4-(2-methylpropyl)phenyl]propionic acid (180293-49-6)

Guidance literature:

With potassium hydroxide; In methanol; tert-butyl alcohol; for 15h;

DOI:10.1016/0040-4020(96)00411-5

upstream raw materials:

ethyl 2-fluoro-2-(4-isobutylphenyl)propanoate

2-fluoro-2-(4-isobutylphenyl)propanol

2-fluoro-2-(4-isobutylphenyl)propanenitrile

1,1-bis(trimethylsilyloxy)-2-(4-isobutylphenyl)propene

Downstream raw materials:

methyl 2-fluoro-2-[4-(2-methylpropyl)phenyl]propionate

di(naphthalen-1-yl)methyl 2-fluoro-2-(4-isobutylphenyl)propanoate

di(naphthalen-1-yl)methyl 2-fluoro-2-(4-isobutylphenyl)propanoate

(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

Refernces

• 1、 Tengeiji, Atsushi,Shiina, Isamu. "A new method for production of chiral 2-aryl-2-fluoropropanoic acids using an effective kinetic resolution of racemic 2-aryl-2-fluoropropanoic acids". experimental part. p. 7356 - 7378. Retrieved 2012/09/05.
• 2、 Fujisawa, Hidehito,Fujiwara, Tomoya,Takeuchi, Yoshio,Omata, Kenji. "Synthesis and optical resolution of 2-aryl-2-fluoropropionic acids, fluorinated analogues of Non-steroidal Anti-inflammatory Drugs (NSAIDs)". . p. 524 - 528. Retrieved 2007/10/03.