4-Trifluoromethylsalicylic acid Chemical Properties

Melting point:

178 °C

Boiling point:

286.4±40.0 °C(Predicted)

Density 

1.539±0.06 g/cm3(Predicted)

vapor pressure 

0.013-0.076Pa at 25℃

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

pka

2.45±0.10(Predicted)

form 

Solid

color 

White to Off-White

InChI

InChI=1S/C8H5F3O3/c9-8(10,11)4-1-2-5(7(13)14)6(12)3-4/h1-3,12H,(H,13,14)

InChIKey

XMLFPUBZFSJWCN-UHFFFAOYSA-N

SMILES

C(O)(=O)C1=CC=C(C(F)(F)F)C=C1O

LogP

3.21

CAS DataBase Reference

328-90-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HazardClass 

IRRITANT

HS Code 

29189900

4-Trifluoromethylsalicylic acid Usage And Synthesis

Chemical Properties

White to off-white solid

Uses

The active metabolite of Triflusal; inhibits cardiac hypertrophy in vitro and in vivo by blocking the NF-κB signaling pathway.

Definition

ChEBI: 2-Hydroxy-4-trifluoromethyl benzoic acid is a hydroxybenzoic acid. It is functionally related to a salicylic acid.

Synthesis

General procedure for the synthesis of 2-hydroxy-4-(trifluoromethyl)benzoic acid from 4-trifluoromethylbenzoic acid: III. Pd(II)-catalyzed tert-butyl hydroxylation reaction (General Method 02): Pd(OAc)2 (11.2 mg, 0.05 mmol), 4-trifluoromethylbenzoic acid (0.5 mmol), benzoquinone (54.0 mg, 0.5 mmol), KOAc (98.0 mg, 1 mmol), and N,N-dimethylacetamide (1.5 mL) were added to a 50 mL high-pressure reactor, and the unit was equipped with a magnetic stir bar. After filling the reactor with O2 (20 atm), it was evacuated and filled again with O2 (5 atm, repeated twice). The reaction mixture was stirred at 115 °C for 15 h and subsequently cooled to room temperature. Post-reaction treatment and purification of the crude product was carried out as described previously for hydroxylation under 1 atm O2 conditions.

References

[1] Journal of the American Chemical Society, 2009, vol. 131, # 41, p. 14654 - 14655
[2] Patent: WO2011/37929, 2011, A2. Location in patent: Page/Page column 14; 19-20

4-Trifluoromethylsalicylic acid(328-90-5)Related Product Information

• 4'-(Trifluoromethyl)acetophenone
• Trifluoromethanesulfonic acid
• 2-Hydroxy-6-methylbenzoic acid
• CHLOROPHOSPHONAZO III
• 3-Aminobenzotrifluoride
• 2-Methylbenzotrifluoride
• 3-(Trifluoromethyl)benzoic acid
• Salicylic acid
• 4-(Trifluoromethyl)cinnamic acid
• (Trifluoromethyl)trimethylsilane
• 4-Methylsalicylic acid
• 3-Hydroxybenzoic acid
• 2'-Hydroxy-3-phenylpropiophenone
• 2-(Trifluoromethyl)benzoic acid
• 2-(Trifluoromethyl)benzyl chloride
• 5-Methylsalicylic acid
• 4-(Trifluoromethyl)benzoic acid
• 3-(Trifluoromethyl)benzaldehyde