63968-85-4

Basic information

• Product Name: 2-(TRIFLUOROMETHOXY)BENZONITRILE
• Synonyms: 2-(TRIFLUOROMETHOXY)BENZONITRILE;O-TRIFLUOROMETHOXYBENZONITRILE;o-Cyanotrifluoromethoxybenzene;2-(Trifluoromethoxy)benzonitrile 97%;2-(Trifluoromethoxy)benzonitrile97%;2-(TrifluoroMethoxy)benzonitrile(o-TrifluoroMethoxybenzonitrile);O-trifluoromethyl-methoxybenzonitrile
• CAS NO: 63968-85-4
• Molecular Formula: C₈H₄F₃NO
• Molecular Weight: 187.12
• EINECS: 264-584-0
• Product Categories: Aromatic Nitriles;Nitrile;Fluorine series
• Mol File: 63968-85-4.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 80 °C
• Flash Point: 80-82°C/15mm
• Appearance: /
• Density: 1,245 g/cm3
• Vapor Pressure: 0.305mmHg at 25°C
• Refractive Index: 1.449
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 2-(TRIFLUOROMETHOXY)BENZONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(TRIFLUOROMETHOXY)BENZONITRILE(63968-85-4)
• EPA Substance Registry System: 2-(TRIFLUOROMETHOXY)BENZONITRILE(63968-85-4)

Safety Data

• Hazard Codes: T,Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-23-36/37-9
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 63968-85-4(Hazardous Substances Data)

Usage

Chemical Properties

Colorless to pale yellow liquid

Uses

2-(Trifluoromethoxy)benzonitrile is used for the synthesis of 4-(2-fluorophenoxy)quinoline derivatives as selective c-Met inhibitors.

InChI:InChI=1/C8H4F3NO/c9-8(10,11)13-7-4-2-1-3-6(7)5-12/h1-4H

Upstream product

• 456-55-3 1-trifluoromethoxybenzene 
• 1130-90-1 1-naphthyl cyanate 
• 57830-55-4 2-((trifluoromethyl)sulfonyl)pyridine 
• 100-47-0 benzonitrile 
• 927-84-4 bis(trifluoromethyl)peroxide 
• 1535-75-7 2-trifluoromethoxy aniline 
• 175205-64-8 2-(trifluoromethoxy)benzylamine 

Downstream Products

• 1597517-00-4 (5-methyl-2-[1,2,3]triazol-2-yl-phenyl)-{(S)-2-[3-(2-trifluoromethoxyphenyl)-[1,2,4]oxadiazol-5-yl]pyrrolidin-1-yl}methanone 
• 926247-77-0 C₈H₆F₃NOS 
• 307989-55-5 5-nitro-2-trifluoromethoxybenzoic acid 
• 307989-54-4 2-(5-isocyanato-2-trifluoromethoxyphenyl)benzoxazole 

Relevant articles and documents

Electrochemical Trifluoromethoxylation of (Hetero)aromatics with a Trifluoromethyl Source and Oxygen

Trifluoromethoxylated aromatics (ArOCF3) are valuable structural motifs in the area of drug discovery due to the enhancement of their desired physicochemical properties upon the introduction of the trifluoromethoxy group (CF3O). Although significant progress has been made recently in the introduction of CF3O group into aromatics, current methods either require the use of expensive trifluoromethoxylation reagents or require harsh reaction conditions. We present a conceptually new and operationally simple protocol for the direct C?H trifluoromethoxylation of (hetero)aromatics by the combination of the readily available trifluoromethylating reagent and oxygen under electrochemical reaction conditions. This reaction proceeds through the initial generation of CF3 radical followed by conversion to CF3O radical, addition to (hetero)aromatics and rearomatization. The utility of this electrochemical trifluoromethoxylation is illustrated by the direct incorporation of CF3O group into a variety of (hetero)aromatics as well as bio-relevant molecules.

Photocatalytic trifluoromethoxylation of arenes and heteroarenes in continuous-flow

The first example of photocatalytic trifluoromethoxylation of arenes and heteroarenes under continuous-flow conditions is described. Application of continuous-flow microreactor technology allowed to reduce the residence time up to 16 times in comparison t

Design, synthesis and biological evaluation of novel 4-(2-fluorophenoxy)quinoline derivatives as selective c-Met inhibitors

Two novel series of 6,7-disubstituted-4-(2-fluorophenoxy)quinoline derivatives bearing 1H-imidazole-4-carboxamido or (E)-3-hydrosulfonylacrylamido motifs (16–31 and 32–42) were designed, synthesized and evaluated for their in vitro cytotoxic activity. Most of the compounds exhibited moderate to excellent potency against tested three cell lines, and fifteen compounds were further examined for their inhibitory activity against c-Met kinase. The most promising compound 16 (c-Met kinase [IC50]?=?1.1?nM) demonstrated high selectivity and remarkable cytotoxicity against HT-29, MKN-45 and A549 cells with IC50values of 0.08, 0.22 and 0.07?μM, which were 3.1-, 1.4- and 2.1-fold more active than Foretinib. The preliminary structure-activity relationships as well as molecular docking disclosed that 1H-imidazole-4-carboxamido as a linker was of great importance for the antitumor activity.