13630-19-8

Basic information

• Product Name: 2-Methylbenzotrifluoride
• Synonyms: 2-(TRIFLUOROMETHYL)TOLUENE;2-METHYLBENZOTRIFLUORIDE;1-METHYL-2-TRIFLUOROMETHYL-BENZENE;ALPHA,ALPHA,ALPHA-TRIFLUORO-O-XYLENE;2-(Trifluoromethyl)toluene~alpha,alpha,alpha-Trifluoro-o-xylene;2-Methylbenzotrifuoride;2-Methylbenzotrifluoride/2-Trifluoromethyltoluene;2-Methylbenzotrifluoride, 97+%
• CAS NO: 13630-19-8
• Molecular Formula: C₈H₇F₃
• Molecular Weight: 160.14
• EINECS: -0
• Product Categories: Trifluoromethylbenzene serise;Aromatic Halides (substituted);Aromatics;Intermediates;Aryl;Building Blocks;C9 to C12;Chemical Synthesis;Halogenated Hydrocarbons;New Products for Chemical Synthesis;Organic Building Blocks;Fluorine series
• Mol File: 13630-19-8.mol

Chemical Properties

• Melting Point: 125-126 °C
• Boiling Point: 125-126°C
• Flash Point: 125-126°C
• Appearance: /
• Density: 1,174 g/cm3
• Refractive Index: 1.435
• Storage Temp.: Sealed in dry,Room Temperature
• BRN: 1940501
• CAS DataBase Reference: 2-Methylbenzotrifluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Methylbenzotrifluoride(13630-19-8)
• EPA Substance Registry System: 2-Methylbenzotrifluoride(13630-19-8)

Safety Data

• Hazard Codes: Xi,F,Xn
• Statements: 34-36/37/38-10-22
• Safety Statements: 26-36/37/39-16
• RIDADR: 3261
• HazardClass: 3
• PackingGroup: III
• Hazardous Substances Data: 13630-19-8(Hazardous Substances Data)

Usage

Uses

Used in the Chemical Industry:
2-Methylbenzotrifluoride is used as an intermediate for the preparation of benzotrifluoride compounds. It serves as a key building block in the synthesis of a wide range of organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals. Its unique reactivity and stability make it a valuable precursor in the development of novel compounds with specific applications.
Used in the Pharmaceutical Industry:
In the pharmaceutical industry, 2-Methylbenzotrifluoride is utilized as a starting material for the synthesis of various drug candidates. Its unique structure and reactivity allow for the development of new molecules with potential therapeutic properties. The compound can be further functionalized and modified to create a diverse array of pharmaceutical agents.
Used in the Agrochemical Industry:
2-Methylbenzotrifluoride also finds application in the agrochemical industry, where it is used as a precursor for the synthesis of various agrochemicals, such as pesticides and herbicides. Its unique chemical properties enable the development of novel compounds with improved efficacy and selectivity, contributing to more effective and environmentally friendly agricultural practices.
Used in the Electronics Industry:
In the electronics industry, 2-Methylbenzotrifluoride can be used as a component in the development of advanced materials for semiconductors and other electronic devices. Its unique electronic properties and stability make it a promising candidate for the creation of new materials with enhanced performance characteristics.

InChI:InChI=1S/C8H7F3/c1-6-4-2-3-5-7(6)8(9,10)11/h2-5H,1H3

Upstream product

• 88-16-4 1-chloro-2-(trifluoromethyl)benzene 
• 149-73-5 trimethyl orthoformate 
• 195062-59-0 2-methylphenylboronic acid pinacol ester 
• 16419-60-6 2-Methylphenylboronic acid 
• 615-37-2 ortho-methylphenyl iodide 
• 95-46-5 2-methylphenyl bromide 
• 120120-26-5 (trifluoromethyl)triethylsilane 
• 95-49-8 2-methylchlorobenzene 
• 12083-24-8 tricarbonyl(η(6)-toluene)chromium 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 2926-29-6 Langlois reagent 
• 108-88-3 toluene 
• 118-90-1 ortho-methylbenzoic acid 
• 93683-27-3 perfluoro-2,4-dimethyl-3-ethylpent-3-yl radical 

Downstream Products

• 1126479-89-7 4,4,5,5-tetramethyl-2-(3-methyl-4-(trifluoromethyl)phenyl)-1,3,2-dioxaborolane 
• 1247072-49-6 C₂₂H₂₅F₃N₂O₃Si 
• 1247072-51-0 C₂₂H₂₅F₃N₂O₃Si 
• 7399-49-7 1-methyl-2-(prop-1-en-2-yl)benzene 
• 1074-92-6 1-tert-butyl-2-methyl-benzene 
• 65492-63-9 N-(4-chlorophenyl)-2-methylbenzamide 
• 1024-64-2 (2,4,6-trimethylphenyl)-(2-methylphenyl)-methanone 
• 89976-12-5 1-methyl-4-nitro-2-(trifluoromethyl) benzene 

Relevant articles and documents

One-pot sandmeyer trifluoromethylation and trifluoromethylthiolation

Practical one-pot procedures were developed for both Sandmeyer-type trifluoromethylations and trifluoromethylthiolations. Starting from broadly available (hetero)aromatic amines, various benzotrifluorides were synthesized in high yields via in situ diazotization and copper-mediated trifluoromethylation using the inexpensive Ruppert-Prakash trifluoromethylating reagent. In the presence of sodium thiocyanate as a sulfur source, aryl trifluoromethyl thioethers are exclusively formed.

Methyl 3-Oxa-ω-fluorosulfonylperfluoropentanoate: a Versatile Trifluoromethylating Agent for Organic Halides

Methyl 3-oxa-ω-fluorosulfonylperfluoropentanoate FSO2CF2CF2OCF2CO2Me 1, prepared through the reaction of readily available ICF2CF2OCF2CF2SO2F and SO3 followed by MeOH, is a very convenient trifluoromethylating agent; in the presence of copper(I) iodide, 1 not only reacts with vinyl, benzyl allyl, phenyl iodides and bromides, but also with aryl chlorides to give the corresponding trifluoromethyl compounds in moderate to high yield; a probable reaction mechanism is proposed.

Synthesis of 2-methyl-1,5-dinitro-3- and 2-methyl-1,3-dinitro-5-(trifluoromethyl)benzenes and their transformation into 6-nitro-4-(trifluoromethyl)- and 4-nitro-6-(trifluoromethyl)-1H-indoles

A facile two-step synthesis of 2-methyl-1,5-dinitro-3- and 2-methyl-1,3-dinitro-5-(trifluoromethyl)benzenes is described. The first step is the nitration of otho- and para-methylbenzoic acids to furnish the corresponding dinitroacids. The dinitroacids then react with sulfur tetrafluoride to provide the corresponding trifluoromethylated products. The latter are easily transformed into 6-nitro-4-(trifluoromethyl)- and 4-nitro-6-(trifluoromethyl)-1H-indoles by applying the Batcho-Leimgruber synthetic protocol.

Flash Thermolysis of Aryl Trifluoroacetates: A New Approach to Trifluoromethylated Aromatic Compounds

Flash thermolysis of aryl trifluoroacetates yield trifluoromethyl aromatic compounds along with trifluoromethoxy compounds.

Phosphovanadomolybdic acid catalyzed direct C-H trifluoromethylation of (hetero)arenes using NaSO2CF3 as the CF3 source and O2 as the terminal oxidant

A direct C-H trifluoromethylation of (hetero)arenes using NaSO2CF3 (Langlois' reagent) as the CF3 source and O2 as the terminal oxidant has been developed. In the presence of catalytic amounts of phosphovanadomolybdic acids, such as H6PV3Mo9O40, various kinds of substituted benzenes and heteroaromatic compounds could be converted into the corresponding trifluoromethylated products.

Use of methyllithium in metal/halogen exchange; a mild and efficient method for the synthesis of ortho substituted toluenes

Methyllithium, in the presence of excess methyl iodide, can be used to convert suitably substituted aromatic bromides to the corresponding toluenes under mild conditions and in high yield.

Generation of trifluoromethylcopper from chlorodifluoroacetate

In the presence of fluoride ion, methyl chlorodifluoroacetate undergoes halide ion-promoted decarboxylation to give trifluoromethide which can be trapped with cuprous iodide.The resulting trifluoromethyl copper reagent has been observed spectroscopically and can be trapped with aryl iodides to give the corresponding trifluoromethylaromatic compound.

Ligand-free trifluoromethylation of iodoarenes by use of 2-Aryl-2-trifluoromethylbenzimidazoline as new trifluoromethylating reagent

N-Methyl 2-aryl-2-trifluoromethylbenzimidazolines were synthesized and utilized in the trifluoromethylation reaction of iodoarenes in the presence of copper(I) salt and base. Iodoarenes bearing electron-donating and electron-withdrawing groups were tolerant to this reaction in the absence of a ligand and gave trifluorotoluene derivatives in good to high yields.

Comparative profiling of well-defined copper reagents and precursors for the trifluoromethylation of aryl iodides

A number of copper reagents were compared for their effectiveness in trifluoromethylating 4-iodobiphenyl, 4-iodotoluene, and 2-iodotoluene. Yields over time were plotted in order to refine our understanding of each reagent performance, identify any bottlenecks, and provide more insight into the rates of the reactions. Interestingly, differences in reactivity were observed when a welldefined [LCuCF3] complex was employed directly or generated in situ from precursors by published reports. Relative reactivities were also found to highly dependent on the nature of the iodoarenes.

Cross-Coupling through Ag(I)/Ag(III) Redox Manifold

In ample variety of transformations, the presence of silver as an additive or co-catalyst is believed to be innocuous for the efficiency of the operating metal catalyst. Even though Ag additives are required often as coupling partners, oxidants or halide scavengers, its role as a catalytically competent species is widely neglected in cross-coupling reactions. Most likely, this is due to the erroneously assumed incapacity of Ag to undergo 2e? redox steps. Definite proof is herein provided for the required elementary steps to accomplish the oxidative trifluoromethylation of arenes through AgI/AgIII redox catalysis (i. e. CEL coupling), namely: i) easy AgI/AgIII 2e? oxidation mediated by air; ii) bpy/phen ligation to AgIII; iii) boron-to-AgIII aryl transfer; and iv) ulterior reductive elimination of benzotrifluorides from an [aryl-AgIII-CF3] fragment. More precisely, an ultimate entry and full characterization of organosilver(III) compounds [K]+[AgIII(CF3)4]? (K-1), [(bpy)AgIII(CF3)3] (2) and [(phen)AgIII(CF3)3] (3), is described. The utility of 3 in cross-coupling has been showcased unambiguously, and a large variety of arylboron compounds was trifluoromethylated via [AgIII(aryl)(CF3)3]? intermediates. This work breaks with old stereotypes and misconceptions regarding the inability of Ag to undergo cross-coupling by itself.