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| | 4-Trifluoromethylsalicylic acid Basic information |
| Product Name: | 4-Trifluoromethylsalicylic acid | | Synonyms: | 4-(Trifluoromethyl)salicylic acid, 2-Carboxy-5-(trifluoromethyl)phenol, 4-Carboxy-3-hydroxybenzotrifluoride;4-(TrifluoroMethyl)salicylic acid, water ≤0.3%;α,α,α-Trifluoro-2,4-cresotic Acid;4- threefluorine Methylsalicylate;4-(TrifluoroMethyl)benzoic Acid, 97+%;p-Trifluoromethylsalicylicacid;4-(TRIFLUOROMETHYL)SALICYLIC ACID;2-HYDROXY-4-(TRIFLUOROMETHYL)BENZOIC ACID | | CAS: | 328-90-5 | | MF: | C8H5F3O3 | | MW: | 206.12 | | EINECS: | 700-368-9 | | Product Categories: | Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Aromatics;Aromatic Carboxylic Acids, Amides, Anilides, Anhydrides & Salts;328-90-5 | | Mol File: | 328-90-5.mol |  |
| | 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) | | form | Solid | | pka | 2.45±0.10(Predicted) | | 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) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39 | | WGK Germany | WGK 2 | | HazardClass | IRRITANT | | HS Code | 29189900 | | Storage Class | 6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects | | Hazard Classifications | Acute Tox. 3 Oral
Aquatic Chronic 3
Eye Dam. 1
Skin Irrit. 2 |
| | 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 Preparation Products And Raw materials |
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