67515-59-7

Basic information

• Product Name: 4-Fluoro-3-(trifluoromethyl)benzonitrile
• Synonyms: 3-(TRIFLUOROMETHYL)-4-FLUOROBENZONITRILE;5-CYANO-2-FLUOROBENZOTRIFLUORIDE;4-FLUORO-3-(TRIFLUOROMETHYL)BENZONITRILE;BUTTPARK 45\01-76;5-Cyano-2-fluorobenzotrifluoride~alpha,alpha,alpha,4-Tetrafluoro-m-tolunitrile;4-Fluoro-3-(Trifluromethyl)Benzonitrile;4-Fluoro-3-Trifluoromethylbenzonitrile 3-Trifluoromethyl-4-fluorobenzonitrile;à,à,à,4-tetrafluoro-m-tolunitrile
• CAS NO: 67515-59-7
• Molecular Formula: C₈H₃F₄N
• Molecular Weight: 189.11
• Product Categories: blocks;Carboxes;FluoroCompounds;Aromatic Nitriles;Miscellaneous;Benzotrifluoride Series
• Mol File: 67515-59-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 66 °C
• Boiling Point: 194°C
• Flash Point: 193-195°C
• Appearance: /
• Density: 1,323 g/cm
• Vapor Pressure: 0.291mmHg at 25°C
• Refractive Index: 1.443
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water.
• BRN: 1960344
• CAS DataBase Reference: 4-Fluoro-3-(trifluoromethyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-3-(trifluoromethyl)benzonitrile(67515-59-7)
• EPA Substance Registry System: 4-Fluoro-3-(trifluoromethyl)benzonitrile(67515-59-7)

Safety Data

• Hazard Codes: T,Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-45-36-36/37-23-9
• RIDADR: 3276
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 67515-59-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow crystal

Uses

It finds it uses as a pharmaceutical intermediate.

InChI:InChI=1/C8H3F4N/c9-7-2-1-5(4-13)3-6(7)8(10,11)12/h1-3H

Upstream product

• 2357-47-3 4-Fluoro-3-trifluoromethylaniline 
• 1194-02-1 4-fluorobenzonitrile 
• 76-05-1 trifluoroacetic acid 
• 75-63-8 Bromotrifluoromethane 
• 16495-77-5 [(4-chlorophenyl)thio]pentafluorobenzene 

Downstream Products

• 735331-03-0 4-(8-azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzonitrile 
• 735331-04-1 4-(8-azabicyclo[3.2.1]oct-8-yl)-3-(trifluoromethyl)benzylamine 
• 735330-63-9 4-azepan-1-yl-3-(trifluoromethyl)benzylamine 
• 635702-33-9 3-trifluoromethyl-4-(2-(S)-butoxy)benzoic acid 
• 1100712-21-7 3-trifluoromethyl-4-[bis(2-hydroxyethyl)-amino)benzonitrile 
• 864297-32-5 4-(3-oxo-pyrazolidin-1-yl)-3-trifluoromethyl-benzonitrile 
• 773849-16-4 4-(piperazin-1-yl)-3-trifluoromethyl-benzoic acid 
• 871795-91-4 4-(2-methyl-[1,3]dioxolan-2-ylmethoxy)-3-trifluoromethylbenzonitrile 
• 720000-06-6 4-(4,5,6,7-tetrahydro-benzoimidazol-1-yl)-3-trifluoromethyl-benzonitrile 
• 904311-38-2 4-(methylsulfonyl)-3-(trifluoromethyl)benzonitrile 
• 507239-93-2 4-(2-methyl-4-pyrrolidin-1-yl-quinolin-7-ylmethoxy)-3-trifluoromethyl-benzonitrile 
• 507241-08-9 4-(4-chloro-2-methyl-quinolin-7-ylmethoxy)-3-trifluoromethyl-benzonitrile 
• 507241-28-3 4-(2,6-Dimethyl-4-pyrrolidin-1-yl-quinolin-7-ylmethoxy)-3-trifluoromethyl-benzonitrile 
• 184163-56-2 (2-trifluoromethyl-4-cyano-phenyl)-hydrazine 

Relevant articles and documents

Palladium-Catalyzed Cyanation under Mild Conditions: A Case Study to Discover Appropriate Substrates among Halides and Pseudohalides

A case study has been effectively carried out to identify a suitable substrate among halides and pseudohalides for the palladium-catalyzed cyanation reactions under mild conditions. Among the various substrates considered for evaluation, aryl pentafluorobenzenesulfonates and nonaflates were identified to be the best substrates when compared to corresponding halides and pseudohalides. The substoichiometric use of nontoxic, environmentally benign potassium hexacyanoferrate as a cyanide source and exceptionally milder conditions further highlights the significance of the protocol developed. A wide range of electronically biased and sterically challenging substrates provided the corresponding the nitriles in good to excellent yields.

Rhodium-catalyzed transformation of heteroaryl aryl ethers into heteroaryl fluorides

A rhodium complex catalyzed the conversion of the C-O bond of heteroaryl aryl ethers to the C-F bond. The reaction of (4-chlorophenylthio)pentafluorobenzene with heteroaryl aryl ethers provided heteroaryl fluorides and heteroaryl (4-chlorophenylthio)tetrafluorophenyl ethers; this involved the cleavage of a single heteroaryl C-O bond under equilibrium conditions. The reaction of heteroaryl aryl ethers with 2-fluorobenzothiazole in which two heteroaryl and aryl C-O bonds were cleaved provided heteroaryl fluorides and aryl fluorides. The reactions were applicable to five-membered and six-membered heteroaryl aryl ethers and also to diaryl ethers possessing one or two electron-withdrawing groups.

Synthesis of 3-trifluoromethyl-4-halobenzonitriles

The practical synthetic method for a series of substantially novel fluorine-containing polyfunctional aromatic compounds, 3-trifluoromethyl-4-halobenzonitriles [halo = Cl, Br, and F], was established by using copper-cyano complexes as effective Sandmeyer cyanating reagents.