350-96-9

Usage

Uses

Used in Organic Synthesis:
p-Toluidine Trifluoroacetamide is used as a synthetic intermediate for the production of a wide range of organic compounds. Its unique chemical structure allows it to be a versatile component in the synthesis of various molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, p-Toluidine Trifluoroacetamide is used as a key component in the development of new drugs. Its reactivity and structural properties make it a valuable asset in the synthesis of novel therapeutic agents, potentially contributing to the treatment of various diseases and medical conditions.
Used in Chemical Research:
p-Toluidine Trifluoroacetamide also finds application in chemical research, where it is employed as a reagent or starting material for the investigation of new reaction pathways and the development of innovative synthetic methods. This contributes to the advancement of chemical knowledge and the discovery of new chemical processes.
Used in Dye and Pigment Industry:
Additionally, p-Toluidine Trifluoroacetamide may be utilized in the dye and pigment industry as a precursor for the synthesis of various dyes and pigments. Its chemical properties make it suitable for the production of colorants used in a wide range of applications, from textiles to plastics and printing inks.

InChI:InChI=1/C9H8F3NO/c1-6-2-4-7(5-3-6)13-8(14)9(10,11)12/h2-5H,1H3,(H,13,14)

Upstream product

• 96254-05-6 2-(trifluoroacetyloxy)pyridine 
• 106-49-0 p-toluidine 
• 2101-86-2 p-methylazidobenzene 
• 76-05-1 trifluoroacetic acid 
• 2923-18-4 sodium 2,2,2-trifluoroacetate 
• 455-14-1 4-trifluoromethylphenylamine 
• 354-38-1 2,2,2-trifluoroacetamide 
• 106-43-4 para-chlorotoluene 
• 108-24-7 acetic anhydride 
• 146408-42-6 3,3,3-Trifluoro-1-phenyl-2-[(E)-p-tolylimino]-propan-1-ol 
• 13081-18-0 ethyl-3,3,3-trifluoropyruvate 
• 1310569-09-5 bis(N-(p-methylphenyl)trifluoroacetimidoyl) disulfide 
• 106-38-7 para-bromotoluene 
• 624-31-7 4-tolyl iodide 

Downstream Products

• 644-08-6 4-Methylbiphenyl 
• 112983-31-0 N-butyl-N-trifluoroacetyl-p-toluidine 
• 623-08-5 N-methyl-p-toluidine 
• 6876-66-0 4,4'-dimethylbenzanilide 
• 1374845-71-2 FeCu(C₅H₄P(C₆H₅)2)2NCOCF₃C₆H₄CH₃ 
• 1353889-36-7 5-amino-N'-((5-cyanopyrazolo[1,5-a]pyridin-3-yl)methylene)-N,2-dimethylbenzenesulfonohydrazide 
• 1353889-35-6 N-(3-(2-((5-cyanopyrazolo[1,5-a]pyridin-3-yl)methylene)-1-methylhydrazinylsulfonyl)-4-methylphenyl)-2,2,2-trifluoroacetamide 
• 1353889-44-7 2-methyl-5-(2,2,2-trifluoroacetamido)benzenesulfonyl chloride 
• 1353889-43-6 5-methyl-2-(2,2,2-trifluoroacetamido)benzenesulfonyl chloride 
• 1185254-52-7 dimethyl 2-(2,2,2-trifluoro-N-p-tolylacetamido)-3-(cyclohexylimino)methylene-succinate 
• 126855-72-9 N-(p-Tolyl)-2,2,2-trifluoroacetimidoyl chloride 
• 128691-96-3 N-(2-Amino-4-methyl-phenyl)-2,2,2-trifluoro-acetamide 
• 112983-34-3 (-)-10-butyl-7-methyl-3-(S)-α-methylbenzyl-5-deazaflavin 
• 112983-33-2 (+)-10-butyl-7-methyl-3-(R)-α-methylbenzyl-5-deazaflavin 

Relevant academic research and scientific papers

Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy

Hormone therapy targeting estrogen receptors is widely used clinically for the treatment of breast cancer, such as tamoxifen, but most of them are partial agonists, which can cause serious side effects after long-term use. The use of selective estrogen receptor down-regulators (SERDs) may be an effective alternative to breast cancer therapy by directly degrading ERα protein to shut down ERα signaling. However, the solely clinically used SERD fulvestrant, is low orally bioavailable and requires intravenous injection, which severely limits its clinical application. On the other hand, double- or multi-target conjugates, which are able to synergize antitumor activity by different pathways, thus may enhance therapeutic effect in comparison with single targeted therapy. In this study, we designed and synthesized a series of novel dual-functional conjugates targeting both ERα degradation and histone deacetylase inhibiton by combining a privileged SERD skeleton 7-oxabicyclo[2.2.1]heptane sulfonamide (OBHSA) with a histone deacetylase inhibitor side chain. We found that substituents on both the sulfonamide nitrogen and phenyl group of OBHSA unit had significant effect on biological activities. Among them, conjugate 16i with N-methyl and naphthyl groups exhibited potent antiproliferative activity against MCF-7 cells, and excellent ERα degradation activity and HDACs inhibitory ability. A further molecular docking study indicated the interaction patterns of these conjugates with ERα, which may provide guidance to design novel SERDs or PROTAC-like SERDs for breast cancer therapy.

Metal-free synthesis of biaryls from aryl sulfoxides and sulfonanilides via sigmatropic rearrangement

Treatment of aryl sulfoxides and sulfonanilides with trifluoroacetic anhydride resulted in the dehydrative metal-free construction of the corresponding unsymmetrical biaryls. The reaction would proceed via (1) the activation of aryl sulfoxide with the anhydride, (2) interrupted Pummerer reaction of the resulting arylsulfonium with sulfonanilide, (3) [3,3] sigmatropic rearrangement to cleave the transient S–N bond and to form the prospective biaryl C–C bond, and (4) global aromatization. The choice of the amino protecting group is crucial, and only N-sulfonylanilines, i.e., sulfonanilides, could participate in the formation of biaryls.

Exploring the PROTAC degron candidates: OBHSA with different side chains as novel selective estrogen receptor degraders (SERDs)

As the mutant estrogen receptor (ER) continues to be characterized, breast cancer is becoming increasingly difficult to cure when treated with hormone therapy. In this regard, a strategy to selectively and effectively degrade the ER might be an effective alternative to endocrine therapy for breast cancer. In a previous study, we identified a novel series of 7-oxabicyclo[2.2.1]heptene sulfonamide (OBHSA) compounds as full ER antagonists while lacking the prototypical ligand side chain that has been widely used to induce antagonism of ERα. Further crystal structure studies and phenotypic assays revealed that these compounds are selective estrogen receptor degraders (SERDs) with a new mechanism of action. However, from a drug discovery point of view, there still is room to improve the potency of these OBHSA compounds. In this study, we have developed new classes of SERDs that contain the OBHSA core structure and different side chains, e.g., basic side chains, long alkyl acid side chains, and glycerol ether side chains, to simply mimic the degrons of proteolysis targeting chimera (PROTAC) and then investigated the structure-activity relationships of these PROTAC-like hybrid compounds. These novel SERDs could effectively inhibit MCF-7 cell proliferation and demonstrated good ERα degradation efficacy. Among the SERDs, compounds 17d, 17e and 17g containing a basic side chain with a N-trifluoroethyl substituent and a para methoxyl group at the phenyl group of the sulfonamide turned out to be the best candidates for ER degraders. A further docking study of these compounds with ERα elucidates their structure-activity relationships, which provides guidance to design new PROTAC degrons targeting ER for breast cancer therapy. Lastly, easy modification of these PROTAC-like SERDs enables further fine-tuning of their pharmacokinetic properties, including oral availability.

Carbon-Carbon Bond Formation of Trifluoroacetyl Amides with Grignard Reagents via C(O)-CF3 Bond Cleavage

The reaction of trifluoroacetyl amides with Grignard reagent for the substitution of CF3 group with various alkyl or aryl groups is described. A variety of aryl, quinolin-8-yl, and (hetero)alkyl functional groups as well as F, Cl, and Br atoms are well tolerated. These moisture-stable and easily available trifluoroacetyl amides can be conveniently obtained and used as new versatile precursors for isocyanates. The control experiments show that the reaction proceeds via an isocyanate intermediate and/or alkoxide/amide dual anionic intermediate.

Synthetic method of trifluoroacetanilide derivative

The invention belongs to the technical field of organic synthetic intermediate, and more specifically relates to a method used for catalytic synthesis of a trifluoroacetanilide derivative under catalytic effect of copper. The method comprises following steps: 1, dimethyl sulfoxide, an aniline derivative, ethyl trifluoropyruvate, and cuprous chloride are delivered into a pressure-resistant reaction tube, the pressure-resistant reaction tube is sealed with a plug, and reaction is carried out for 12h in oil bath at 80 DEG C with magnetic stirring; 2, after reaction, extraction is carried out with ether, obtained organic phase substances are mixed, and reduced pressure distillation is carried out so as to remove most of the solvents, and an obtained mixed solution is subjected to column chromatography separation purification with an eluent composed of petroleum ether and ethyl acetate at a volume ratio of 2:1-10:1 so as to obtain a finished product. The trifluoroacetanilide derivative can be widely used in the fields such as organic synthesis, medicine industry, and pesticide industry; cost is low; operation is simple; the substances are widely available; yield is high; and application prospect is promising.

Switching reaction pathways of trifluoromethylated thiobenzanilides by choice of different oxidative systems

Trifluoromethylated thiobenzanilides are efficiently converted to 2-trifluoromethylbenzothiazoles via intramolecular oxidative cyclization under CAN/NaHCO3 oxidation, while the dimerized products with "-S-S-" bond linkage are obtained when PIDA

A simple and efficient method for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene

A simple and efficient one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid and triphosgene is reported. A mixed trifluoroacetic anhydride generated in situ reacts with a variety of arylamines to give the corresponding trifluroacetamides in high yields.

A one-pot procedure for trifluoroacetylation of arylamines using trifluoroacetic acid as a trifluoroacetylating reagent

A convenient procedure for the preparation of aryl trifluoroacetamides from aryl amines is described that employs 2-4 M equiv of trifluoroacetic acid in refluxing xylene as a trifluoroacetylating agent. Addition of an amount of pyridine that is equimolar to the amount of trifluoroacetic acid present in the reaction mixture facilitates the trifluoroacetylation of rather basic arylamines.

One-pot synthesis of highly functionalized stable ketenimines of 2,2,2-trifluoro-N-aryl-acetamides

Three-component reaction of alkyl isocyanides and dialkyl acetylenedicarboxylates in the presence of 2,2,2-trifluoro-N-aryl-acetamides in dichloromethane at ambient temperature afforded dialkyl 2-(N-(aryl)-2,2,2-trifluoroacetamido)-3-(alkylimino) methylene-succinate derivatives in excellent yields.

Copper-catalyzed synthesis of primary arylamines from aryl halides and 2,2,2-trifluoroacetamide

A catalytic method was developed to synthesize primary arylamines from the corresponding aryl bromides and iodides under mild conditions (yields = 80-99%). Crystalline 2,2,2-trifluoroacetamide was used as ammonia surrogate and CuI/N,N′-dimethyl ethylenediamine was used as catalyst to achieve the C-N cross-coupling.