447-60-9

Basic information

• Product Name: 2-(Trifluoromethyl)benzonitrile
• Synonyms: α,α,α-trifluoro-o-tolunitrile;2-(Trifluoromethyl)benzonitrile 98%;2-(Trifluoromethyl)benzonitrile98%;ALPHA,ALPHA,ALPHA-TRIFLUORO-ORTHO-TOLUNITRILE;2-TRIFLUOROMETHYLBENZONITRILE (ALPHA,ALPHA,ALPHA-TRIFLUORO-O-TOLUNITRILE);a,a,a-Trifluoro-o-tolunitrile;o-(Trifluoromethyl)cyanobenzene;o-Cyanobenzotrifluoride
• CAS NO: 447-60-9
• Molecular Formula: C₈H₄F₃N
• Molecular Weight: 171.12
• EINECS: 207-184-3
• Product Categories: Aromatic Nitriles;Nitrile
• Mol File: 447-60-9.mol

Chemical Properties

• Melting Point: 7.5 °C(lit.)
• Boiling Point: 88-90 °C (15 mmHg)
• Flash Point: 194 °F
• Appearance: colorless to light yellow liquid
• Density: 1.294 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.256mmHg at 25°C
• Refractive Index: n20/D 1.4632(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Sensitive: Lachrymatory
• BRN: 2048152
• CAS DataBase Reference: 2-(Trifluoromethyl)benzonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(Trifluoromethyl)benzonitrile(447-60-9)
• EPA Substance Registry System: 2-(Trifluoromethyl)benzonitrile(447-60-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-52/53-20/21/22
• Safety Statements: 61-36-24/25
• RIDADR: UN 3276 6.1/PG 3
• WGK Germany: 2
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 447-60-9(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
2-(Trifluoromethyl)benzonitrile is used as a key intermediate in the synthesis of symmetrical N,N′-alkylidine bisamides. Its unique chemical properties allow it to react with tert-butyl acetate in the presence of sulfuric acid to give the corresponding N-tert-butyl amides, which are valuable in the production of various organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(Trifluoromethyl)benzonitrile is used as a building block for the development of new drugs. Its reactivity and structural properties make it a versatile component in the design and synthesis of novel pharmaceutical compounds.
Used in Material Science:
2-(Trifluoromethyl)benzonitrile is also utilized in material science for the development of new materials with specific properties. Its incorporation into polymers and other materials can lead to enhanced performance characteristics, such as improved stability, reactivity, or selectivity.

InChI:InChI=1/C8H4F3N/c9-8(10,11)7-4-2-1-3-6(7)5-12/h1-4H

Upstream product

• 83-41-0 2,3-dimethylnitrobenzene 
• 2042-37-7 o-cyanobromobenzene 
• 77152-08-0 trifluoromethylcopper(I) 
• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 
• 151-50-8 potassium cyanide 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 612-24-8 o-nitrobenzonitrile 
• 2314-97-8 iodotrifluoromethane 
• 75-63-8 Bromotrifluoromethane 
• 3872-23-9 Copper(I) trifluoromethanethiolate 
• 98-08-8 α,α,α-trifluorotoluene 
• 100-17-4 para-methoxynitrobenzene 
• 460-19-5 ethanedinitrile 
• 2635-68-9 2-trichloromethyl-benzonitrile 

Downstream Products

• 360-64-5 2-(trifluoromethyl)benzamide 
• 433-97-6 2-trifluoromethylbenzoic acid 
• 3048-01-9 o-trifluoromethylbenzylamine 
• 40067-66-1 N'-hydroxy-2-(trifluoromethyl)benzene-carboximidamide 
• 156215-39-3 2-(2-(trifluoromethyl)phenyl)benzo[d]thiazole 
• 40018-09-5 o-Trifluormethylbenzoacetodinitril 
• 529-19-1 2-Methylbenzonitrile 
• 88-99-3 benzene-1,2-dicarboxylic acid 
• 304663-19-2 N-(tert-butyl)-2-(trifluoromethyl)benzamide 
• 40067-66-1 N-Hydroxy-2-trifluoromethyl-benzamidine 
• 886496-67-9 2-(trifluoromethyl)benzothioamide 
• 577-62-8 ethyl ortho-α,α,α-trifluoromethylbenzoate 
• 2944-97-0 2-(trifluoromethyl)benzylamine hydrochloride 
• 40018-17-5 1-methyl-5-(2-trifluoromethyl-phenyl)-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one 

Relevant articles and documents

Preparation method of o-trifluoromethylbenzamide

The present invention discloses a method for preparing o-trifluoromethyl benzamide. The preparation method comprises the following steps: (1) in an organic solvent, the 2-nitrobenzotrifluoride and fluorinated salts are denitrified as shown below to obtain o-fluorobenzotrifluoride; (2) in an organic solvent, the o-fluortrifluorotoluene and cyanidylation reagent are defluoride cyanidation reaction as shown below to obtain o-trifluoromethylbenzonitrile; (3) in the presence of alkali, the o-trifluoromethylbenzonitrile, hydrogen peroxide hydrolysis reaction as shown below. The preparation method is simple to treat, the product purity is high, the impurities are small, and the yield is high.

Synthesis method 2 - trifluoromethyl benzamide

The invention discloses a synthesis method of 2 -trifluoromethylbenzamide, which comprises the following steps of 2, 3 -dichloro-trifluorotoluene serving as a raw material and fluorinating. The preparation 2 -trifluoro -6 -cyano-trifluorotoluene is prepared by cyano substitution, 2 -fluoro -6 -cyanobenzotrifluoride is subjected to hydrogenation and dehydrochlorination, and 2 -trifluoromethylbenzamide is prepared by first hydrolyzing and dehydrochlorinating and dechlorinating. 2 - Trifluoromethylbenzamide is synthesized by simple reaction, and the method has the characteristics of cheap and easily available raw materials, no participation of the isomer 2 - fluorine -3 - chlorine - trifluorotoluene isomers in subsequent reaction and easy removal. In each reaction step, flammable and explosive, highly toxic or non-volatile agents commonly used in the existing synthetic method are not used, and harm to operating personnel and in the environment is avoided. , The total yield of the product reaches above 67%, and the purity is 97% or more.

Development and Molecular Understanding of a Pd-Catalyzed Cyanation of Aryl Boronic Acids Enabled by High-Throughput Experimentation and Data Analysis

A synthetic method for the palladium-catalyzed cyanation of aryl boronic acids using bench stable and non-toxic N-cyanosuccinimide has been developed. High-throughput experimentation facilitated the screen of 90 different ligands and the resultant statistical data analysis identified that ligand σ-donation, π-acidity and sterics are key drivers that govern yield. Categorization into three ligand groups – monophosphines, bisphosphines and miscellaneous – was performed before the analysis. For the monophosphines, the yield of the reaction increases for strong σ-donating, weak π-accepting ligands, with flexible pendant substituents. For the bisphosphines, the yield predominantly correlates with ligand lability. The applicability of the designed reaction to a wider substrate scope was investigated, showing good functional group tolerance in particular with boronic acids bearing electron-withdrawing substituents. This work outlines the development of a novel reaction, coupled with a fast and efficient workflow to gain understanding of the optimal ligand properties for the design of improved palladium cross-coupling catalysts.

Recyclable and Reusable Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O System for Cyanation of Aryl Chlorides with Potassium Ferrocyanide

Pd(OAc)2/XPhos–SO3Na in a mixture of poly(ethylene glycol) (PEG-400) and water is shown to be a highly efficient catalyst for the cyanation of aryl chlorides with potassium ferrocyanide. The reaction proceeded smoothly at 100 or 120?oC with K2CO3 or KOAc as base, delivering a variety of aromatic nitriles in good to excellent yields. The isolation of the crude products is facilely performed by extraction with cyclohexane and more importantly, both expensive Pd(OAc)2 and XPhos–SO3Na in PEG-400/H2O system could be easily recycled and reused at least six times without any apparent loss of catalytic efficiency. Graphical Abstract: Palladium-catalyzed cyanation of aryl chlorides with potassium ferrocyanide leading to aryl nitriles by using Pd(OAc)2/XPhos–SO3Na/PEG-400/H2O as a highly efficient and recyclable catalytic system is described.[Figure not available: see fulltext.]

Acceptorless dehydrogenation of amines to nitriles catalyzed by N-heterocyclic carbene-nitrogen-phosphine chelated bimetallic ruthenium (II) complex

We have developed a clean, atom-economical and environmentally friendly route for acceptorless dehydrogenation of amines to nitriles by combining a new dual N-heterocyclic carbene-nitrogen-phosphine ligand R(CNP)2 (R = o-xylyl) with a ruthenium precursor [RuCl2(η6-C6H6)]2. In this system, the electronic and steric factors of amines had a negligible influence on the reaction and a broad range of functional groups were well tolerated. All of the investigated amines could be converted to nitriles in good yield of up to 99% with excellent selectivity. The unprecedented catalytic performance of this system is attributed to the synergistic effect of two ruthenium centers chelated by R(CNP)2 and a plausible reaction mechanism is proposed according to the active species found via in situ NMR and HRMS.

HCl·DMPU-assisted one-pot and metal-free conversion of aldehydes to nitriles

We report an efficient HCl·DMPU assisted one-pot conversion of aldehydes into nitriles. The use of HCl·DMPU as both an acidic source as well as a non-nucleophilic base constitutes an environmentally mild alternative for the preparation of nitriles. Our protocol proceeds smoothly without the use of toxic reagents and metal catalysts. Diverse functionalized aromatic, aliphatic and allylic aldehydes incorporating various functional groups were successfully converted to nitriles in excellent to quantitative yields. This protocol is characterized by a broad substrate scope, mild reaction conditions, and high scalability. This journal is

SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)

A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.

Method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by Ru coordination compound

The invention discloses a method for catalyzing receptor-free dehydrogenation of primary amine to generate nitrile by a Ru coordination compound. The method comprises: adding a Ru coordination compound, an alkali, a primary amine and an organic solvent into a reaction test tube according to a mol ratio of 1:100:(100-500):1000-3000, and carrying out a stirring reaction under the condition of 80 to120 DEG C; and when gas chromatography monitors that the raw materials completely disappear, stopping the reaction, collecting the reaction solution, centrifuging the reaction solution, taking the supernatant, extracting with dichloromethane, merging the organic phases, drying, filtering, evaporating the organic solvent under reduced pressure to obtain a filtrate, and carrying out column chromatography purification on the filtrate to obtain the target product nitrile. According to the invention, the catalyst is good in activity, single in catalytic system, good in product selectivity, simple in subsequent treatment and good in system universality after the reaction is finished, has a good catalytic effect on various aryl, alkyl and heteroaryl substituted primary amines, and also has a gooddehydrogenation performance on secondary amines.

Nickel-Catalyzed Decarbonylative Cyanation of Acyl Chlorides

Ni-catalyzed decarbonylative cyanation of acyl chlorides with trimethylsilyl cyanide has been achieved. This transformation is applicable to the synthesis of an array of nitrile compounds bearing a wide range of functional groups under neutral conditions. The step-by-step experimental studies revealed that the reaction sequences of the present catalytic reaction are oxidative addition, transmetalation, decarbonylation, and reductive elimination.

Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO

A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.