58458-14-3

Basic information

• Product Name: 2-Amino-3-trifluoromethylbenzonitrile
• Synonyms: 2-AMINO-3-(TRIFLUOROMETHYL)BENZONITRILE;2-Amino-3-(trifluoromethyl)benzonitrile 98%;2-Amino-3-(trifluoromethyl)benzonitrile98%
• CAS NO: 58458-14-3
• Molecular Formula: C₈H₅F₃N₂
• Molecular Weight: 186.13
• Product Categories: Nitrile;Fluorine series
• Mol File: 58458-14-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 62-65 °C
• Boiling Point: 263.9 °C at 760 mmHg
• Flash Point: 113.4 °C
• Appearance: /
• Density: 1.37 g/cm³
• Vapor Pressure: 0.01mmHg at 25°C
• Refractive Index: 1.499
• Storage Temp.: 2-8°C(protect from light)
• PKA: -1.32±0.10(Predicted)
• CAS DataBase Reference: 2-Amino-3-trifluoromethylbenzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Amino-3-trifluoromethylbenzonitrile(58458-14-3)
• EPA Substance Registry System: 2-Amino-3-trifluoromethylbenzonitrile(58458-14-3)

Safety Data

• Hazard Codes: Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39
• RIDADR: 3439
• Hazardous Substances Data: 58458-14-3(Hazardous Substances Data)

Usage

Uses

2-Amino-3-trifluoromethylbenzonitrile is a useful intermediate for the preparation of chloro and trifluoromethyl derivatives of benzisothiazoles.

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

• 304650-02-0 N-(2-cyanophenyl)pyridine-2-carboxamide 
• 58458-13-2 2-bromo-6-trifluoromethylphenylamine 
• 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

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

Relevant articles and documents

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.

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.

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