58458-14-3

Usage

Uses

Used in Pharmaceutical Industry:
2-Amino-3-trifluoromethylbenzonitrile is used as a key intermediate for the preparation of chloro and trifluoromethyl derivatives of benzisothiazoles. These derivatives exhibit a wide range of biological activities, including antimicrobial, anti-inflammatory, and anticancer properties. The introduction of the trifluoromethyl group enhances the lipophilicity and metabolic stability of the resulting compounds, leading to improved pharmacokinetic profiles.
Used in Agrochemical Industry:
In the agrochemical industry, 2-Amino-3-trifluoromethylbenzonitrile serves as a versatile intermediate for the synthesis of novel pesticides and herbicides. The trifluoromethyl group imparts increased volatility and soil adsorption properties to the final products, resulting in enhanced efficacy and reduced environmental impact.
Overall, 2-Amino-3-trifluoromethylbenzonitrile is a valuable chemical intermediate with diverse applications in both the pharmaceutical and agrochemical industries, owing to its unique structural features and reactivity.

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 17, p. 65, 1980 DOI: 10.1002/jhet.5570170113

InChI:InChI=1/C8H5F3N2/c9-8(10,11)6-3-1-2-5(4-12)7(6)13/h1-3H,13H2

Upstream product

• 58458-13-2 2-bromo-6-trifluoromethylphenylamine 
• 304650-02-0 N-(2-cyanophenyl)pyridine-2-carboxamide 
• 91534-20-2 3-Azido-7-trifluoromethyl-benzo[c]isothiazole 
• 74409-80-6 3-Amino-7-trifluoromethyl-2,1-benzoisothiazole 
• 91534-21-3 2-Thionitroso-3-trifluoromethyl-benzonitrile 
• 542-92-7 cyclopenta-1,3-diene 
• 74396-78-4 7-Trifluoromethylisatin β-oxime 

Downstream Products

• 1052092-64-4 (E)-2-(3,3-diethyltriaz-1-enyl)-3-(trifluoromethyl)benzonitrile 
• 1052092-62-2 (E)-2-(3,3-diisopropyltriaz-1-enyl)-3-(trifluoromethyl)benzonitrile 
• 1429782-12-6 C₁₂H₁₇NO 

Relevant academic research and scientific papers

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.

Palladium/N-Heterocyclic carbene catalyzed mono- and double-cyanation of aryl halides using potassium ferrocyanide trihydrate under aerobic conditions

Abstract A practical palladium/N-heterocyclic carbene catalyzed procedure for the mono- and double-cyanation of aryl halides is described using inexpensive, easy-to-handle and nontoxic potassium ferrocyanide trihydrate {K4[Fe(CN)6]·3H2O} as the cyanating agent. The reaction does not require an anhydrous solvent, or the exclusion of air or moisture. A variety of electron-rich and electron-deficient aryl halides are efficiently converted into their corresponding nitriles and dicarbonitriles.

Process for producing trifluoromethylbenzylamines

The invention relates to a process for producing a trifluotomethylbenzylamine represented by the following general formula (1), 1where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4. The process includes hydrogenating a trifluoromethylbenzonitrile by hydrogen in an organic solvent in the presence of ammonia and a catalyst containing a platinum group element. This trifluoromethylbenzonitrile is represented by the following general formula (2), 2where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine at an extremely high yield.

Process for producing trifluoromethylbenzylamines

The invention relates to a process for producing a trifluoromethylbenzylamine represented by the following general formula (1). This process includes hydrogenating a trifliuoromethylbenzonitrile represented by the following general formula (2) by hydrogen in an organic solvent in the presence of ammonia, using a Raney catalyst, where each R independently represents a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, an alkyl group having a carbon atom number of 1-4, an alkoxy group having a carbon atom number of 1-4, an amino group, a hydroxyl group or a trifluoromethyl group, and n represents an integer from 0 to 4, where R and n are defined as above. With this process, it is possible to obtain the trifluoromethylbenzylamine easily and inexpensively at an extremely high yield.

Generation of Thionitroso Compounds by Benzisothiazole Ring Opening

Oxidation of 3-amino-2-phenylindazole (3) or thermolysis of 3-azido-2-phenylindazole (4) gives 2-cyanoazobenzene (5) quantitatively; thermolysis or photolysis of 3-azido-2,1-benzisothiazoles (1) induces similar ring opening to give the transient 2-cyanoth

Substituted cyano,trifluoromethylphenyl linear triazenes

The compounds of this invention are substituted cyano,trifluoromethylphenyl linear triazenes having pharmacological activity. In particular, these compounds have anorectic and anti-obesity activity. A preferred compound is 1,3-bis(2-cyano-5-trifluoromethylphenyl)triazene.