Chemical Properties
white to light yellow crystal powder
Uses
3,5-Bis(trifluoromethyl)benzoic acid is a useful synthetic intermediate, and is a derivative of Benzoic acid (B203900). 3,5-Bis(trifluoromethyl)benzoic acid has also been identified as a major metabolite of a series of 3,5-bis(trifluoromethyl)benzyl ethers in vitro, and is hypothesized to result via oxidation of the benzylic position.
Application
3,5-bis(trifluoromethyl)benzoic acid is an intermediate in synthesizing pharmaceutical compounds, which are substance P (neurokinin-1) receptor antagonists. In particular, such compounds are substance P (neurokinin-1) receptor antagonists, which are helpful, e.g., in treating inflammatory diseases, psychiatric disorders, and emesis.
Synthesis Reference(s)
The Journal of Organic Chemistry, 68, p. 3695, 2003
DOI: 10.1021/jo026903n
General Description
3,5
-Bis(trifluoromethyl)benzoic acid is a significant metabolite formed during metabolism of 3,5-
bis(trifluoromethyl)benzyl ether via oxidation.
Synthesis
The synthesis of 3,5-bis(trifluoromethyl)benzoic acid was carried out by 1,3-dibromo-5,5-dimethyl-acetonitrile urea with 1,3-bis(trifluoromethyl)benzene to produce 3,5-bis(trifluoromethyl)bromobenzene in 98% yield and 99% selectivity. Then 3,5-bis(trifluoromethyl)bromobenzene was used as raw material to synthesize 3,5-bis(trifluoromethyl)benzoic acid in more than 72% yield.
