2338-75-2

Basic information

• Product Name: 4-(TRIFLUOROMETHYL)PHENYLACETONITRILE
• Synonyms: 4-(TRIFLUOROMETHYL)PHENYLACETONITRILE;4-TRIFLUOROMETHYLBENZYLCYANIDE;P-TRIFLUOROMETHYLBENZYL CYANIDE;TIMTEC-BB SBB006690;Benzeneacetonitrile, 4-(trifluoromethyl)-;p-Trifluoromethylphenylacetonitrile;4-(TRIFLUOROMETHYL)PHENYLACETONITRILE, 9 8%;4-(Trifluoromethyl)phenylacetonitrile 98%
• CAS NO: 2338-75-2
• Molecular Formula: C₉H₆F₃N
• Molecular Weight: 185.15
• EINECS: 219-052-2
• Product Categories: Nitrile;C8 to C9;Cyanides/Nitriles;Nitrogen Compounds;Fluorine series
• Mol File: 2338-75-2.mol
• Article Data: 16

Chemical Properties

• Melting Point: 47-49 °C(lit.)
• Boiling Point: 131-132 °C20 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: white crystalline mass or needles
• Density: 1,23 g/cm3
• Vapor Pressure: 0.0278mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: Sealed in dry,Room Temperature
• Water Solubility: Insoluble in water
• BRN: 909641
• CAS DataBase Reference: 4-(TRIFLUOROMETHYL)PHENYLACETONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(TRIFLUOROMETHYL)PHENYLACETONITRILE(2338-75-2)
• EPA Substance Registry System: 4-(TRIFLUOROMETHYL)PHENYLACETONITRILE(2338-75-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-20/21/22/36/37/38
• Safety Statements: 26-37/39-26/36/37/39-36/37/39
• RIDADR: 3439
• WGK Germany: 3
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 2338-75-2(Hazardous Substances Data)

Usage

Description

4-(Trifluoromethyl)phenylacetonitrile is an organic compound characterized by its white crystalline mass or needle-like appearance. It is a derivative of phenylacetonitrile with a trifluoromethyl group at the para position, which imparts unique chemical and physical properties to the molecule.

Uses

Used in Organic Semiconductors:
4-(Trifluoromethyl)phenylacetonitrile is used as a key building block in the synthesis of novel n-type organic semiconductors, specifically for the preparation of 1,4-bis[2-cyano-2-(4-(trifluoromethyl)phenyl)vinyl]benzenecyano-substituted distyrylbenzene derivatives. These organic semiconductors are of interest due to their potential applications in various electronic devices, such as organic field-effect transistors (OFETs) and organic photovoltaics (OPVs), where their n-type characteristics can enhance device performance and efficiency.

InChI:InChI=1/C9H6F3N/c10-9(11,12)8-3-1-7(2-4-8)5-6-13/h1-4H,5H2

Upstream product

• 143-33-9 sodium cyanide 
• 939-99-1 4-trifluoromethylbenzyl chloride 
• 402-49-3 4-bromomethyltrifluoromethylbenzene 
• 151-50-8 potassium cyanide 
• 2942-58-7 diethyl cyanophosphonate 
• 18293-53-3 2-trimethylsilylacetonitrile 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 402-51-7 4-(trifluoromethyl)phenylmagnesium bromide 
• 583-02-8 ethyl 4-(trifluoromethyl)benzoate 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 928664-98-6 4-isoxazoleboronic acid pinacol ester 
• 1071-36-9 sodium cyanoacetate 

Downstream Products

• 29786-44-5 1-(4-(trifluoromethyl)phenyl)cyclobutane-1-carbonitrile 
• 32445-87-7 2-methyl-2-(4-(trifluoromethyl)phenyl)propanenitrile 
• 32857-62-8 4-Trifluoromethylphenylacetic acid 
• 775-00-8 2-(4-trifluoromethyl-phenyl)-ethylamine 
• 146725-29-3 Z-2-(4-trifluoromethylphenyl)-3-(4-methoxyphenyl)acrylonitrile 
• 117998-08-0 (E)-3-Hydroxy-2-(4-trifluoromethyl-phenyl)-acrylonitrile 

Relevant articles and documents

Rapid and Simple Access to α-(Hetero)arylacetonitriles from Gem-Difluoroalkenes

A scalable cyanation of gem-difluoroalkenes to (hetero)arylacetonitrile derivatives was developed. This strategy features mild reaction conditions, excellent yields, wide substrate scope, and broad functional group tolerance. Significantly, in this reacti

Two-step cyanomethylation protocol: Convenient access to functionalized aryl- and heteroarylacetonitriles

A two-step protocol has been developed for the introduction of cyanomethylene groups to metalated aromatics through the intermediacy of substituted isoxazoles. A palladium-mediated cross-coupling reaction was used to introduce the isoxazole unit, followed by release of the cyanomethylene function under thermal or microwave-assisted conditions. The intermediate isoxazoles were shown to be amenable to further functionalization prior to deprotection of the sensitive cyanomethylene motif, allowing access to a wide range of aryl- and heteroaryl-substituted acetonitrile building blocks.

Synthesis of α-aryl esters and nitriles: Deaminative coupling of α-aminoesters and α-aminoacetonitriles with arylboronic acids

Transition-metal-free synthesis of α-aryl esters and nitriles using arylboronic acids with α-aminoesters and α-aminoacetonitriles, respectively, as the starting materials has been developed. The reaction represents a rare case of converting C(sp3)-N bonds into C(sp3)-C(sp2) bonds. The reaction conditions are mild, demonstrate good functional-group tolerance, and can be scaled up. Touch base: A transition-metal-free protocol for the synthesis of α-aryl esters and nitriles by deaminative coupling is presented. Strong bases and transition-metal catalysts are not needed. The new synthetic method uses readily available starting materials and demonstrates wide substrate scope.