144433-66-9

Basic information

• Product Name: Benzoic acid, 2-hydroxy-6-(trifluoromethyl)-
• CAS NO: 144433-66-9
• Molecular Formula: C8H5F3O3
• Molecular Weight: 206.121
• Mol File: 144433-66-9.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Benzoic acid, 2-hydroxy-6-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzoic acid, 2-hydroxy-6-(trifluoromethyl)-(144433-66-9)
• EPA Substance Registry System: Benzoic acid, 2-hydroxy-6-(trifluoromethyl)-(144433-66-9)

Safety Data

• Hazardous Substances Data: 144433-66-9(Hazardous Substances Data)

Upstream product

• 124-38-9 carbon dioxide 
• 98-17-9 3-Trifluoromethylphenol 
• 368422-28-0 2-methoxymethoxy-6-(trifluoromethyl)benzoic acid 
• 402-45-9 4-hydroxybenzotrifluoride 
• 651-91-2 2,3-bis(trifluoromethyl)-7-oxabicyclo<2,2,1>hepta-2,5-diene 
• 334018-79-0 1-(trifluoromethyl)-3-(methoxymethoxy)benzene 

Downstream Products

• 1024605-95-5 2-hydroxy-6-trifluoromethylbenzoic acid methyl ester 

Relevant articles and documents

Novel spiropiperidine-based stearoyl-CoA desaturase-1 inhibitors: Identification of 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-5-(trifluoromethyl)-3,4-dihydrospiro[chromene-2,4′-piperidine]

Cyclization of the benzoylpiperidine in lead compound 2 generated a series of novel and highly potent spiropiperidine-based stearoyl-CoA desaturase (SCD)-1 inhibitors. Among them, 1′-{6-[5-(pyridin-3-ylmethyl)-1,3,4-oxadiazol-2-yl]pyridazin-3-yl}-5-(trifluoromethyl)-3,4-dihydrospiro[chromene-2,4′-piperidine] (19) demonstrated the most powerful inhibitory activity against SCD-1, not only in vitro but also in vivo (C57BL/6 J mice). With regard to the pharmacological evaluation, 19 showed powerful reduction of the desaturation index in the plasma of C57BL/6 J mice on a non-fat diet after a 7-day oral administration (q.d.) without causing notable abnormalities in the eyes or skin up to the highest dose (3 mg/kg) in our preliminary analysis.

Fluorophenols and (trifluoromethyl)phenols as substrates of site-selective metalation reactions: To protect or not to protect

O-Methoxymethyl (MOM) protected fluorophenols can be cleanly metalated and subsequently be submitted to site-selective electrophilic substitution. The 2- and 4-isomers exhibit ambivalent reactivity: deprotonation occurs at the position adjacent to the oxygen when butyllithium is employed whereas the position adjacent to the fluorine is attacked by the superbasic mixture of butyllithium and potassium tert-butoxide (LIC-KOR). The MOM-protected (trifluoromethyl)-phenols react exclusively at oxygen-neighboring positions. The meta isomer provides another example of optional site selectivity, undergoing hydrogen/metal exchange at the 2-position with the LIC-KOR reagent and at the 6-position with sec-butyllithium. Unprotected (trifluoromethyl)phenols can also be ortho-metalated after O-deprotonation, although the products are formed in only moderate yields.