327-74-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-5-cyanobenzotrifluoride is used as a key intermediate in the design and synthesis of 4-phenylpyrrole derivatives. These derivatives have been found to act as androgen receptor antagonists, which are effective against prostate cancer cells. 2-Amino-5-cyanobenzotrifluoride's unique structure allows for the development of targeted therapies with potential applications in cancer treatment.

Upstream product

• 557-21-1 dicyanozinc 
• 97760-97-9 4-iodo-2-(trifluoromethyl)aniline 
• 445-02-3 4-bromo-2-trifluoromethyl-aniline 
• 88-17-5 2-(trifluoromethyl)benzenamine 
• 773837-37-9 sodium cyanide 
• 887144-94-7 Togni's reagent II 
• 873-74-5 4-Aminobenzonitrile 
• 2926-29-6 Langlois reagent 
• 2314-97-8 iodotrifluoromethane 
• 126222-22-8 N-(4-cyanophenyl)-2-pyridinecarboxamide 

Downstream Products

• 62584-29-6 4-Amino-3-iodo-5-trifluoromethylbenzonitrile 
• 167760-75-0 methyl 4-amino-3-(trifluoromethyl)benzoate 
• 491865-44-2 C₂₈H₃₁F₃N₆OSSi 
• 727993-61-5 4-({3-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-6-methyl-4-[3-(2-pyridinyl)-1H-pyrazol-1-yl]-2-pyridinyl}amino)-3-(trifluoromethyl)benzonitrile 
• 727993-46-6 4-{[4-(1'H-1,3'-bipyrazol-1'-yl)-3-(2-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-6-methyl-2-pyridinyl]amino}-3-(trifuoromethyl)benzonitrile 
• 1274673-02-7 C₁₂H₁₀ClF₃N₂O 
• 1196702-79-0 C₈H₉F₃N₂*ClH 
• 688020-69-1 ethyl 4-amino-3-(trifluoromethyl)benzoate 
• 1094695-60-9 C₁₀H₆ClF₃N₂O 
• 1345724-19-7 4-dibenzylamino-3-trifluoromethyl-benzonitrile 
• 1345724-18-6 4-(5-morpholin-4-yl-[1,6]naphthyridin-7-yl)-2-trifluoromethylphenylamine 
• 1345724-22-2 dibenzyl-[4-(5-chloro-[1,6]naphthyridin-7-yl)-2-trifluoromethylphenyl]amine 
• 1345724-24-4 dibenzyl-[4-(5-morpholin-4-yl-[1,6]naphthyridin-7-yl)-2-trifluoromethylphenyl]amine 

Relevant academic research and scientific papers

Visible-light-mediated direct perfluoroalkylation and trifluoromethylation of free anilines

A mild, operationally simple method for direct perfluoroalkylation and trifluoromethylation of anilines through visible-light-mediated photoredox catalysis from broadly available perfluoroalkyl iodides and free anilines is described. The method provides a facile route for application in drug discovery and development.

Transition metal-free direct C–H trifluoromethyltion of (hetero)arenes with Togni's reagent

A new transition-metal-free direct C–H trifluoromethylation reaction of (hetero)arenes with Togni's reagent was developed. This transformation proceeded smoothly under mild conditions and exhibited good tolerance of many synthetically relevant functional groups. It provided an alternative approach for the synthesis of trifluoromethylated (hetero)arenes.

Preparation method of trifluoromethylated aniline compound

The invention provides a preparation method of a trifluoromethylated aniline compound shown in a formula (IIA) or a formula (IIB). The method comprises the following steps: by taking a mixed solvent of DMF and water in a volume ratio of 1:(1-4) as a reaction medium, adding an aniline compound shown in a formula (IA) or a formula (IB), 1-(trifluoromethyl)-1,2-benziodoxol-3-(1H)-one and a photocatalyst, and reacting for 2-6 hours at room temperature under blue light; and carrying out post-treatment on the obtained reaction mixture to obtain the trifluoromethylated aniline compound as shown in the formula (IIA) or the formula (IIB). According to the method, by the photocatalyst, the reaction is driven to be carried out under the irradiation of visible light, the reaction conditions are mild,the site selectivity is high, the reaction is efficient, green and environment-friendly, the reaction yield can reach 90%, and the product can be prepared by only one step.

Synthetic method of aminobenzotrifluoride and derivant thereof

The invention discloses a synthetic method of aminobenzotrifluoride and a derivant thereof. By adopting a method for performing amino-ortho-position trifluoromethylation on an amino-benzene compound,trifluoromethyl trimethylsilane is used a reaction reagent, free radical substitution reaction is carried out on an amino-ortho-position of the amino-benzene compound and then trifluoromethylation isdirectly carried out, so that a target product is obtained. The method disclosed by the invention has the advantages that raw materials are cheap and easy to obtain, the production is convenient, precious metal is not needed, environmental protection and safety are achieved, and purification is easy to carry out; the method can be developed into an industrial production method. Based on that, according to the synthetic method disclosed by the invention, screening and optimization on synthetic conditions of the compound are also carried out, so that the reaction yield is further improved.

Coordinating Activation Strategy-Induced Selective C?H Trifluoromethylation of Anilines

A simple protocol for the synthesis of 2-(trifluoromethyl)aniline derivatives through a coordinating activation strategy was developed. The reaction showed good reactivity and gave the target products in moderate to good yields. Pleasingly, the directing group could be recovered in excellent yield. Furthermore, this strategy allowed efficient access to the synthesis of floctafenine. A single-electron-transfer mechanism was proposed to be responsible for this trifluoromethylation reaction.

Nickel-Catalyzed Direct C-H Trifluoromethylation of Free Anilines with Togni's Reagent

An efficient nickel-catalyzed C-H trifluoromethylation for the synthesis of trifluoromethylated free anilines using Togni's reagent has been developed. This approach exhibits a good functional group tolerance, good regioselectivity, and chemoselectivity under mild conditions. The newly developed economical one-step method is a better alternative to synthesize trifluoromethylated free anilines.

Preparation method of trifluoromethylamine

The invention relates to a preparation method of trifluoromethylamine. The method includes the following steps that aromatic amine shown in the formula (1) and a trifluoromethyl reagent shown in the formula (2) react in a solvent under the condition that an alkali and/or nickel compound exists, and the trifluoromethylamine compound shown in the formula (3) is generated. According to the preparation method of trifluoromethylamine, aromatic amine and 1-trifluoromethyl-1,2-iodobenzoyl-3(H)-ketone serve as raw materials and react under the condition that the alkali and/or nickel compound exists through the amino positioning effect on aromatic nucleus. The synthesis steps of the method are simple, the cost of the raw materials is low, the production cost of trifluoromethylamine can be greatly reduced, and large-scale industrialized production is promoted.

Photoinduced Charge-Transfer State of 4-Carbazolyl-3-(trifluoromethyl)benzoic Acid: Photophysical Property and Application to Reduction of Carbon?Halogen Bonds as a Sensitizer

The photoinduced persistent intramolecular charge-transfer state of 4-carbazolyl-3-(trifluoromethyl)benzoic acid was confirmed. It showed a higher catalytic activity in terms of yield and selectivity in the photochemical reduction of alkyl halides compared to the parent carbazole. Even unactivated primary alkyl bromides could be reduced by this photocatalyst. The high catalytic activity is rationalized by considering the slower backward single-electron transfer owing to the spatial separation of the donor and acceptor subunits.

Preparation 2-trifluoromethyl-4-substituted aniline compounds

The invention relates to a method for preparing 2-trifluoromethyl-4-substituted phenylamine and 2-trifluoromethyl-4-substituted acetanilide. The method for preparing the2-trifluoromethyl-4-substituted phenylamine and 2-trifluoromethyl-4-substituted acetanilide comprises the following main step: in the presence of sodium trifluoromethanesulfonate and tert-butyl hydroperoxide but no metal salt catalyst and under the stirring condition, maintaining a 4-substituted phenylamine compound (concrete structure shown in a formula II is described in the specification) in a reaction medium of mixture composed of dichloromethane and water at the temperature of 0-25 DEG C for 72-120 hours, so that the 2-trifluoromethyl-4-substituted phenylamine target product is obtained. The preparation method provided by the invention has potential commercial value.

Copper-free direct C-H trifluoromethylation of acetanilides with sodium trifluoromethanesulfinate

A copper-free direct C-H ortho trifluoromethylation of electron-deficient 4-substituted acetanilides using Langlois reagent (NaSO2CF3) as the CF3 source in the presence of tert-butyl hydroperoxide (tBuOOH, TBHP) was developed.