454-92-2

Usage

Uses

Used in Pharmaceutical Industry:
3-(Trifluoromethyl)benzoic acid is used as an intermediate in the synthesis of various pharmaceutical compounds for its unique properties, such as enhanced solubility in dense carbon dioxide. This characteristic can be advantageous in drug formulation and delivery, potentially improving the bioavailability and therapeutic efficacy of the resulting medications.
Used in Chemical Research:
3-(Trifluoromethyl)benzoic acid serves as a valuable research compound for studying the effects of fluorination on the solubility and other chemical properties of organic compounds. Its pKa values in water and methanol provide insights into its acid-base behavior, which can be useful in understanding its reactivity and potential applications in various chemical processes.

InChI:InChI=1/C8H5F3O2/c9-8(10,11)6-3-1-2-5(4-6)7(12)13/h1-4H,(H,12,13)/p-1

Upstream product

• 109-72-8 n-butyllithium 
• 60-29-7 diethyl ether 
• 98-08-8 α,α,α-trifluorotoluene 
• 368-77-4 3-trifluoromethylbenzonitrile 
• 454-89-7 3-Trifluoromethylbenzaldehyde 
• 67-56-1 methanol 
• 401-78-5 3-bromo-1-trifluoromethylbenzene 
• 201230-82-2 carbon monoxide 
• 402-31-3 1,3-bis(trifluoromethyl)benzene 
• 2251-65-2 3-(Trifluoromethyl)benzoyl chloride 
• 124-38-9 carbon dioxide 
• 98-15-7 3-chlorotrifluoromethylbenzene 
• 349-76-8 3'-(trifluoromethyl)acetophenone 
• 392-83-6 o-trifluoromethylphenyl bromide 

Downstream Products

• 349-75-7 3-(trifluoromethyl)benzyl alcohol 
• 2557-13-3 3-trifluoromethylbenzoic acid methyl ester 
• 93669-36-4 N-(3-Imidazol-1-yl-propyl)-3-trifluoromethyl-benzamide 
• 100468-26-6 N-(3-[1,2,4]Triazol-1-yl-propyl)-3-trifluoromethyl-benzamide 
• 56207-24-0 1,2,3,4-Tetrafluoro-5-[4-(3-trifluoromethyl-phenoxy)-butoxy]-benzene 
• 368-77-4 3-trifluoromethylbenzonitrile 
• 303041-26-1 1-[3-(trifluoromethyl)benzoyl]-2,3,5-tribenzoyl-β-D-ribofuranose 
• 380909-18-2 2-isopropoxy-3-(4-{2-[5-(3-trifluoromethyl-phenyl)-[1,2,4]oxadiazol-3-yl]-ethoxy}-phenyl)-propionic acid methyl ester 
• 1027949-53-6 (R)-3-Hydroxy-2-(3-trifluoromethyl-benzoylamino)-propionic acid methyl ester 
• 612844-79-8 phenyl 2-O-(2-deoxy-2-[3-(trifluoromethyl)benzamido]-β-D-glucopyranosyl)-3-azido-3-deoxy-4-O-methyl-1-thio-β-D-glucopyranosiduronamide 
• 500340-01-2 (2S,3S,4S,5R,6R)-3,4,5-Triacetoxy-6-(3-trifluoromethyl-benzoylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Aerobic oxidation of aldehydes to carboxylic acids catalyzed by recyclable ag/c3 n4 catalyst

The oxidation of aldehydes is an efficient methodology for the synthesis of carboxylic acids. Herein we hope to report a simple, efficient and recyclable protocol for aerobic oxidation of aldehydes to carboxylic acid by using C3N4 supported silver nanoparticles (Ag/C3N4) as a catalyst in aqueous solution under mild conditions. Under standard conditions, the corresponding carboxylic acids can be obtained in good to excellent yields. In addition, Ag/C3N4 is convenient for recovery and could be reused three times with satisfactory yields.

Synthesis and structure-activity relationships of new 2-phenoxybenzamides with antiplasmodial activity

The 2-phenoxybenzamide 1 from the Medicines for Malaria Venture Malaria Box Project has shown promising multi-stage activity against different strains of P. falciparum. It was successfully synthesized via a retrosynthetic approach. Subsequently, twenty-one new derivatives were prepared and tested for their in vitro activity against blood stages of the NF54 strain of P. falciparum. Several insights into structure-activity relationships were revealed. The antiplasmodial activity and cytotoxicity of compounds strongly depended on the substitution pattern of the anilino partial structure as well as on the size of substituents. The diaryl ether partial structure had further impacts on the activity. Additionally, several physicochemical and pharmacokinetic parameters were calculated (log P, log D7.4 and ligand efficiency) or determined experimentally (passive permeability and CYP3A4 inhibition). The tert-butyl-4-{4-[2-(4-fluorophenoxy)-3-(trifluoromethyl)benzamido]phenyl}piperazine-1-carboxylate possesses high antiplasmodial activity against P. falciparum NF54 (PfNF54 IC50 = 0.2690 μM) and very low cytotoxicity (L-6 cells IC50 = 124.0 μM) resulting in an excellent selectivity index of 460. Compared to the lead structure 1 the antiplasmodial activity was improved as well as the physicochemical and some pharmacokinetic parameters.

Hydrolysis of amides to carboxylic acids catalyzed by Nb2O5

Hydrolysis of amides to carboxylic acids is an industrially important reaction but is challenging due to the difficulty of cleaving the resonance stabilized amidic C-N bond. Twenty-three heterogeneous and homogenous catalysts were examined in the hydrolysis of acetamide. Results showed that Nb2O5was the most effective heterogeneous catalyst with the greatest yield of acetic acid. A series of Nb2O5catalysts calcined at various temperatures were characterized and tested in the hydrolysis of acetamide to determine the effects of crystal phase and surface properties of Nb2O5on catalytic performance. The high catalytic performance observed was attributed mainly to the facile activation of the carbonyl bond by Lewis acid sites that function even in the presence of basic inhibitors (NH3and H2O). The catalytic studies showed the synthetic advantages of the present method, such as simple operation, catalyst recyclability, additive free, solvent free, and wide substrate scope (>40 examples; up to 95% isolated yield).

Green synthesis method of aromatic acid

The invention discloses a green synthesis method of aromatic acid. Nickel-catalyzed carbonyl insertion is carried out on aryl iodine in the presence of formate, acid anhydride, a phosphine ligand andan organic solvent by using a nickel catalyst to obtain the aromatic acid. Efficient catalytic conversion is realized by utilizing the cheap nickel catalyst, the reaction conditions are mild, and theoperation is simple.

Cobalt-catalyzed carboxylation of aryl and vinyl chlorides with CO2

The transition-metal-catalyzed carboxylation of aryl and vinyl chlorides with CO2 is rarely studied, and has been achieved only with a Ni catalyst or combination of palladium and photoredox. In this work, the cobalt-catalyzed carboxylation of aryl and vinyl chlorides and bromides with CO2 has been developed. These transformations proceed under mild conditions and exhibit a broad substrate scope, affording the corresponding carboxylic acids in good to high yields.

Light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds

Visible light-induced organic reactions are important chemical transformations in organic chemistry, and their efficiency highly depends on suitable photocatalysts. However, the commonly used photocatalysts are precious transition-metal complexes and elaborate organic dyes, which hamper large-scale production due to high cost. Here, for the first time, we report a novel strategy: light and oxygen-enabled sodium trifluoromethanesulfinate-mediated selective oxidation of C-H bonds, allowing high-value-added aromatic ketones and carboxylic acids to be easily prepared in high-to-excellent yields using readily available alkyl arenes, methyl arenes and aldehydes as materials. The mechanistic investigations showed that the treatment of inexpensive and readily available sodium trifluoromethanesulfinate with oxygen under irradiation of light could in situ form a pentacoordinate sulfide intermediate as an efficient photosensitizer. The method represents a highly efficient, economical and environmentally friendly strategy, and the light and oxygen-enabled sodium trifluoromethanesulfinate photocatalytic system represents a breakthrough in photochemistry. This journal is

Nickel-catalyzed carboxylation of aryl iodides with lithium formate through catalytic CO recycling

A protocol for the Ni-catalyzed carboxylation of aryl iodides with formate has been developed with good functional group compatibility for the synthesis of a variety of aromatic carboxylic acids under mild conditions. The reaction tolerates other functionalities for cross-coupling, such as aryl bromide, aryl chloride, aryl tosylate, and aryl pinacol boronate. The reaction proceeds through a carbonylation process with in situ generated carbon monoxide in the presence of a catalytic amount of acetic anhydride and lithium formate, avoiding the use of gaseous CO. The strategy of CO recycling in catalytic amounts is critical for the success of the reaction.

Ni-Catalyzed Carboxylation of C(sp2)-S Bonds with CO2: Evidence for the Multifaceted Role of Zn

Nickel-catalyzed reductive carboxylation reactions of aryl electrophiles typically require the use of metallic reducing agents. At present, the prevailing perception is that these serve as both a source of electrons and as a source of Lewis acids that may aid CO2 insertion into the Ni-C bond. Herein, we provide evidence for the in situ formation of organometallic species from the metallic reductant, a step that has either been ruled out or has been unexplored in catalytic carboxylation reactions with metal powder reductants. Specifically, we demonstrate that Zn(0) acts as a reductant and that Zn(II) generates arylzinc species that might play a role in the C(sp2)-S carboxylation of arylsulfonium salts. Overall, the reductive Ni-catalyzed C(sp2)-S carboxylation reaction proceeds under mild conditions in a non-amide solvent, displays a wide substrate scope, and can be applied to the formal para C-H carboxylation of arenes.

Preparation method of substituted benzoic acid compounds

The invention relates to the field of production of chemical products, in particular to a preparation method of substituted benzoic acid compounds represented as general formula (II) in the description. The preparation method comprises steps as follows: corresponding substituted alkyl benzene represented as general formula (I) in the description is taken as a raw material, dilute nitric acid is taken as a reaction medium, oxygen is taken as an oxidant, an imide compound with a structure represented as formula (III) in the description or formula (IV) in the description is selected as a catalyst, all materials are subjected to catalytic oxidation in a high-pressure kettle, and substituted benzoic acid is prepared, wherein R1 is C1-C4 alkyl and R2 is halogen, nitryl, C1-C4 alkyl, methoxyl andtrifluoromethyl. The green preparation method of the substituted benzoic acid compounds is provided and has the advantages of high production purity, simple preparation, mild reaction conditions, simple aftertreatment, low cost and no pollution.

Picolinamide Assisted Oxidation of CH2 Groups Bound to Organic and Organometallic Compounds Using Ferrocene as a Catalyst

Picolinamide group assisted sp3 C-H bond oxidation of methylene groups to the corresponding carbonyl compounds has been achieved by using simple bottle ferrocene as catalyst and Cu(OAc)2 or tert-butyl peroxybenzoate (TBPB) as oxidant under mild conditions. This method is applicable for picolinamide bound organic as well as organometallic compounds with yields in the range of 46-82%. Control experiments and mechanistic studies indicate that a radical mechanism is responsible for these oxidative transformations in which ferrocene acts as a catalyst.