1939-19-1

Usage

Uses

Used in Pharmaceutical Industry:
N-(2,2-DIMETHYLPROPANOYL)-3-(TRIFLUOROMETHYL)ANILINE is used as an intermediate in the synthesis of Flunixin, a nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. It is particularly effective in managing pain and inflammation in animals, making it a valuable component in veterinary medicine.
As an intermediate, N-(2,2-DIMETHYLPROPANOYL)-3-(TRIFLUOROMETHYL)ANILINE plays a crucial role in the development of other derivatives of Flunixin, which may possess improved pharmacological properties or reduced side effects. This contributes to the ongoing research and development of novel therapeutic agents in the pharmaceutical industry.

InChI:InChI=1/C12H14F3NO/c1-11(2,3)10(17)16-9-6-4-5-8(7-9)12(13,14)15/h4-7H,1-3H3,(H,16,17)

Upstream product

• 3282-30-2 pivaloyl chloride 
• 98-16-8 3-trifluoromethylaniline 
• 62-53-3 aniline 
• 887144-94-7 Togni's reagent II 
• 6625-74-7 N-pivaloylaniline 
• 1538-75-6 2,2-dimethylpropanoic anhydride 
• 75-98-9 Trimethylacetic acid 

Downstream Products

• 54396-44-0 2-methyl-3-trifluoromethylaniline 
• 54396-42-8 ethyl 2-(2-methyl-3-trifluoromethylanilino)nicotinate 
• 38677-85-9 flunixin 
• 1201835-65-5 2,2-dimethyl-1-[2-(3-trifluoromethylphenylamino)phenyl]propan-1-one 
• 129473-02-5 N-[2-(α-hydroxyethyl)-3-trifluoromethylphenyl]-2,2-dimethylpropionamide 
• 150783-50-9 2-methyl-3-pivaloylaminobenzotrifluoride 

Relevant academic research and scientific papers

Equivalent Loading of Directed Arenes in Pd(II)-Catalyzed Oxidative Cross-Coupling of Aryl C-H Bonds at Room Temperature

The unsymmetrical biaryls (Ar1-Ar2) produced by the catalytic cross-couplings of aryl halides (Ar1-halo) with aryl metallics (Ar2-M) in the loading ratio of 1:1 are popular in chemical synthesis. In contrast, there has been less precedence on the same biaryls produced effectively from two normal aryl C-H bonds with equivalent loading. Here, we report that, in a palladium/oxidant/acid catalytic system at room temperature, one arene (Ar1-H, 1 equiv) can highly selectively couple with the other one (Ar2-H, 1 equiv) to afford the target Ar1-Ar2 just by controlling the directing groups and the substituted groups on their phenyl rings. The utility of this one-one cross-coupling is also demonstrated by synthesis of a few bioactive molecules.

Ligand Promoted Olefination of Anilides for Indirectly Introducing Fluorinated Functional Groups via Palladium Catalyst

We report a palladium-catalyzed, ligand promoted, C-H fluorine-containing olefination of anilides with 4-bromo-3,3,4,4-tetrafluorobutene as the fluorinated reagent, which has a potential transformation into other compounds due to its -CF2CF2Br functional group. -CF2CF2H was obtained by using the mild reducing agent sodium borohydride. Bioactive compounds such as aminoglutethimide derivative and propham were well-tolerated in this reaction, both of which highlight the synthetic importance of this method.

Palladium(II)-Catalyzed Oxidative Homo- and Cross-Coupling of Aryl ortho -sp2 C-H Bonds of Anilides at Room Temperature

The preparation of secondary 2,2'-bisanilides has been successfully achieved through an oxidative coupling of aryl ortho-sp2 C-H bonds of anilides in the presence of catalytic Pd(OAc)2 and K2S2O8 as an oxidant in MsOH/CF3CO2H (TFA) at room temperature (25 °C). The aromatic rings of anilides substituted by various electron-donating or electron-withdrawing groups are tolerant in these coupling reactions.

Amine Activation: Synthesis of N-(Hetero)arylamides from Isothioureas and Carboxylic Acids

A novel method for N-(hetero)arylamide synthesis based on rarely explored amine activation, rather than classical acid activation, is reported. The activated amines are easily prepared using a three-component reaction with commercial reagents. The new method shows a broad scope including challenging amides not (efficiently) accessible via classical protocols.

CuCl-catalyzed ortho trifluoromethylation of arenes and heteroarenes with a pivalamido directing group

The CuCl catalyzed direct trifluoromethylation of sp2 C-H bonds has been realized, using the Togni reagent as the CF3 source. This reaction achieves the goal of regio-selectively converting C-H into C-CF 3 with ecological and readily available starting materials.

Improved Process for the Preparation of 2-Methyl-3-trifluoromethylaniline: A Versatile Intermediate for Flunixin Synthesis

A detailed new experimental investigation into the synthesis of Flunixin via 2-methyl-3-trifluoromethylaniline is described.The coupling process between 2-methyl-3-trifluoromethylaniline and 2-chloronicotinate was achieved stoichiometrically and in high yield, when ethylene glycol was used as reaction solvent at 160 deg C.

Preparation of substituted anilino-nicotinic acid derivatives

Substituted anilino-nicotinic acid derivatives are readily prepared from the condensation of two intermediates, 2-alkyl-3-perfluoroalkyl-anilines and alkyl 2-chloronicotinates. The 2-alkyl-3-perfluoroalkyl-aniline intermediate can be prepared via a novel three step synthesis. 3-Perfluoroalkyl-anilines are reacted with an amine directing protecting group reagent to protect the amine. The protected amine is then alkylated, and finally, the directing group is removed to form the 2-alkyl-3-perfluoroalkyl-aniline intermediate. The 2-alkyl-3-perfluoroalkyl-aniline intermediate is condensed with the alkyl 2-chloronicotinate to form the anilino-nicotinic acid derivative.

Quinolyloxyacetamides

Quinoline derivatives of formula: STR1 in which either R 1 denotes trifluoromethyl, R 2 and R 3 form, together with the nitrogen atom to which they are attached, morpholino and R 4 denotes a 4-methylphenyl, 4-chlorophenyl, 2-, 3- or 4-fluorophenyl, 4-meth