2967-66-0

Basic information

• Product Name: Methyl 4-trifluoromethylbenzoate
• Synonyms: The three fluorinated Methyl benzoic acid Methyl ester;4-(TRIFLUOROMETHYL)BENZOIC ACID METHYL ESTER;METHYL ALPHA,ALPHA,ALPHA-TRIFLUORO-P-TOLUATE;METHYL 4-(TRIFLUOROMETHYL)BENZOATE;METHYL P-(TRIFLUOROMETHYL)BENZOATE;RARECHEM AL BF 0111;n-Methyl-4-(Trifluoromethyl) Benzoate;Methyl 4-(Trifluoromethyl)Benoate
• CAS NO: 2967-66-0
• Molecular Formula: C₉H₇F₃O₂
• Molecular Weight: 204.15
• Product Categories: Boronic Acid series;Aromatic Esters;Benzotrifluoride Series;C8 to C9;Carbonyl Compounds;Esters
• Mol File: 2967-66-0.mol

Chemical Properties

• Melting Point: 13-14 °C(lit.)
• Boiling Point: 94-95 °C21 mm Hg(lit.)
• Flash Point: 180 °F
• Appearance: Clear colorless to very pale yellow/Liquid
• Density: 1.268 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.346mmHg at 25°C
• Refractive Index: n20/D 1.451(lit.)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• BRN: 1963288
• CAS DataBase Reference: Methyl 4-trifluoromethylbenzoate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 4-trifluoromethylbenzoate(2967-66-0)
• EPA Substance Registry System: Methyl 4-trifluoromethylbenzoate(2967-66-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 2967-66-0(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
Methyl 4-trifluoromethylbenzoate is used as a chemical intermediate for the synthesis of various compounds, particularly in the pharmaceutical and agrochemical industries. Its trifluoromethyl group provides unique reactivity and properties that can be exploited in the development of new drugs and agrochemicals.
Used in Catalyst Research:
The ester is also used in research for the development of new catalysts, such as MoO2Cl2, which can efficiently catalyze the reduction of Methyl 4-trifluoromethylbenzoate. This research can lead to the discovery of more efficient and selective catalysts for various chemical reactions.
Used in Fluorine Chemistry:
Methyl 4-trifluoromethylbenzoate is used as a building block in fluorine chemistry, where the trifluoromethyl group can be further functionalized or used as a protecting group. This allows for the synthesis of a wide range of fluorinated compounds with potential applications in various fields.
Used in Material Science:
The unique properties of the trifluoromethyl group in Methyl 4-trifluoromethylbenzoate make it a valuable component in the development of new materials with specific properties, such as improved thermal stability, chemical resistance, or electronic properties.

InChI:InChI=1/C9H7F3O2/c1-14-8(13)6-2-4-7(5-3-6)9(10,11)12/h2-5H,1H3

Upstream product

• 186581-53-3 diazomethane 
• 455-24-3 4-trifluoromethylbenzoic acid 
• 67-56-1 methanol 
• 455-19-6 4-Trifluoromethylbenzaldehyde 
• 201230-82-2 carbon monoxide 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 455-13-0 4-Iodobenzotrifluoride 
• 1204296-05-8 methyl 4-trifluoromethylcyclohexanecarboxylate 
• 81290-20-2 (trifluoromethyl)trimethylsilane 
• 99768-12-4 4-methoxycarbonylphenylboronic acid 
• 349-95-1 4-(trifluoromethyl)benzylic alcohol 
• 865-33-8 potassium methanolate 
• 709-63-7 1-(4-trifluoromethylphenyl)ethanone 
• 292638-85-8 acrylic acid methyl ester 

Downstream Products

• 2252-62-2 2-(4-(trifluoromethyl)phenyl)propan-2-ol 
• 112816-01-0 1-<4-(Trifluoromethyl)phenyl>-2-(4-pyrimidinyl)ethenol 
• 85957-45-5 1-(4-(Trifluoromethyl)phenyl)-2-(4(1H)-quinazolinylidene)ethanone 
• 164594-47-2 3-Hydroxy-1-methyl-3-(4-trifluoromethyl-phenyl)-azetidine-2-thione 
• 196934-20-0 4-(trifluoromethyl)benzoic acid t-butyl ester 
• 2924-89-2 1-(α-chloro-isopropyl)-4-trifluoromethyl-benzene 
• 51638-15-4 dimethyl (2-oxo-2-(4-(trifluoromethyl)phenyl)ethyl)phosphonate 
• 1146214-86-9 2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-trifluoropmethylbenzoic acid methyl ester 
• 1146215-05-5 methyl 2,6-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-4-(trifluoromethyl)benzoate 
• 125996-71-6 2-(pyridin-4-yl)-1-(4-(trifluoromethyl)phenyl)ethan-1-one 
• 1240403-34-2 C₁₂H₁₅F₃O₃ 
• 127918-61-0 methyl 4-trifluoromethylbenzenecarbothioate 
• 1060659-95-1 C₁₃H₈F₃N₃O₃S 
• 1345860-98-1 3-acetyl-5-(4-trifluoromethylphenyl)-2-(5-nitrothiophen-2-yl)-2,3-dihydro-1,3,4-oxadiazole 

Relevant articles and documents

Copper-Promoted Conversion of Aromatic Amines into Trifluoromethylated Arenes: One-Pot Sandmeyer Trifluoromethylation

A simple copper-promoted one-pot Sandmeyer trifluoromethylation of aromatic amines with Langlois’ reagent has been demonstrated. The reaction is performed in mild reaction conditions under an air atmosphere with good substrate scope and functional group compatibility. It provides an alternative and straightforward synthetic approach to access a variety of trifluoromethylated arenes.

Catalytic trifluoromethylation of iodoarenes by use of 2-trifluoromethylated benzimidazoline as trifluoromethylating reagent

The trifluoromethylation of iodoarenes was accomplished by use of a 2-trifluoromethylbenzimidazoline derivative as the trifluoromethylating reagent and a catalytic amount of Cu(I) in the presence of 2,2'-bipyridyl as the ligand. Through a mechanistic study, we found that the oxidative addition of the iodoarene to the Cu(I)–CF3 species is the rate-determining step.

Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids

The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.

Hydrazones of 4-(Trifluoromethyl)benzohydrazide as new inhibitors of acetyl- and butyrylcholinesterase

Based on the broad spectrum of biological activity of hydrazide-hydrazones, trifluoromethyl compounds, and clinical usage of cholinesterase inhibitors, we investigated hydrazones obtained from 4-(trifluoromethyl)benzohydrazide and various benzaldehydes or aliphatic ketones as potential inhibitors of acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). They were evaluated using Ellman’s spectrophotometric method. The hydrazide-hydrazones produced a dual inhibition of both cholinesterase enzymes with IC50 values of 46.8-137.7 μM and 19.1-881.1 μM for AChE and BuChE, respectively. The majority of the compounds were stronger inhibitors of AChE; four of them (2-bromobenzaldehyde, 3-(trifluoromethyl)benzaldehyde, cyclohexanone, and camphor-based 2o, 2p, 3c, and 3d, respectively) produced a balanced inhibition of the enzymes and only 2-chloro/trifluoromethyl benzylidene derivatives 2d and 2q were found to be more potent inhibitors of BuChE. 4-(Trifluoromethyl)-N’-[4-(trifluoromethyl)benzylidene]benzohydrazide 2l produced the strongest inhibition of AChE via mixed-type inhibition determined experimentally. Structure-activity relationships were identified. The compounds fit physicochemical space for targeting central nervous systems with no apparent cytotoxicity for eukaryotic cell line together. The study provides new insights into this CF3-hydrazide-hydrazone scaffol.

Oxidative esterification of alcohols by a single-side organically decorated Anderson-type chrome-based catalyst

The direct esterification of alcohols with non-noble metal-based catalytic systems faces great challenges. Here, we report a new chrome-based catalyst stabilized by a single pentaerythritol decorated Anderson-type polyoxometalate, [N(C4H9)4]3[CrMo6O18(OH)3C{(OCH2)3CH2OH}], which can realize the efficient transformation from alcohols to esters by H2O2oxidation in good yields and high selectivity without extra organic ligands. A variety of alcohols with different functionalities including some natural products and pharmaceutical intermediates are tolerated in this system. The chrome-based catalyst can be recycled several times and still keep the original configuration and catalytic activity. We also propose a reasonable catalytic mechanism and prove the potential for industrial applications.

PCl3-mediated transesterification and aminolysis of tert-butyl esters via acid chloride formation

A PCl3-mediated conversion of tert-butyl esters into esters and amides in one-pot under air is developed. This novel protocol is highlighted by the synthesis of skeletons of bioactive molecules and gram-scale reactions. Mechanistic studies revealed that this transformation involves the formation of an acid chloride in situ, which is followed by reactions with alcohols or amines to afford the desired products.

Palladium-Catalyzed Aminocarbonylation of Aryl Halides with N,N-Dialkylformamide Acetals

We developed a protocol for the palladium-catalyzed aminocarbonylation of aryl halides using less-toxic formamide acetals as bench-stable aminocarbonyl sources under neutral conditions. Various aryl (including heteroaryl) halides reacted with N,N-dialkylformamide acetals in the presence of a catalytic amount of tris(dibenzylideneacetone)dipalladium(0)-chloroform adduct and xantphos to give the corresponding aromatic carboxamides at 90–140 °C without any activating agents or bases in up to quantitative chemical yield. This protocol was applied to aryl bromides, aryl iodides, and trifluoromethanesulfonic acid, as well as to relatively less-reactive aryl chlorides. A wide range of functionalities on the aromatic ring of the substrates were tolerated under the aminocarbonylation conditions. The catalytic aminocarbonylation was used to prepare the insect repellent N,N-diethyl-3-methylbenzamide as well as a synthetic intermediate of the dihydrofolate reductase inhibitor triazinate.

Mechanistic Insight into Copper-Mediated Trifluoromethylation of Aryl Halides: The Role of CuI

The synthesis, characterization, and reactivity of key intermediates [Cu(CF3)(X)]-Q+ (X = CF3 or I, Q = PPh4) in copper-mediated trifluoromethylation of aryl halides were studied. Qualitative and quantitative studies showed [Cu(CF3)2]-Q+ and [Cu(CF3)(I)]-Q+ were not highly reactive. Instead, a much more reactive species, ligandless [CuCF3] or DMF-ligated species [(DMF)CuCF3], was generated in the presence of excess CuI. On the basis of these results, a general mechanistic map for CuI-promoted trifluoromethylation of aryl halides was proposed. Furthermore, on the basis of this mechanistic understanding, a HOAc-promoted protocol for trifluoromethylation of aryl halides with [Ph4P]+[Cu(CF3)2]- was developed.

Rational Design and Development of Low-Price, Scalable, Shelf-Stable and Broadly Applicable Electrophilic Sulfonium Ylide-Based Trifluoromethylating Reagents

The development of two highly reactive electrophilic trifluoromethylating reagents (trifluoromethyl)(4-nitrophenyl)bis(carbomethoxy)methylide (1g) and (trifluoromethyl)(3-chlorophenyl)bis(carbomethoxy)methylide (1j) through structure-activity study was described. Under mild conditions, reagent 1g reacted with β-ketoesters and silyl enol ethers to give α-trifluoromethylated-β-ketoesters or α-trifluoromethylated ketones in high yields. In addition, reagent 1g could serve as a trifluoromethyl radical for a variety of trifluoromethylative transformations under visible light irradiation, including radical trifluoromethylation of electron-rich indoles and pyrroles and sodium aryl sulfinates as well as trifluoromethylative difunctionalization with styrene derivatives. On the other hand, as a complimentary, under reductive coupling conditions, reagent 1j reacted with a variety of (hetero)aryl iodides for the formation of trifluoromethylated (hetero)arenes.

Chemical tracer agent for fracturing as well as preparation method and application thereof

The invention relates to a chemical tracer for fracturing and a preparation method and application thereof. The chemical tracer agent is fluoromethyl benzoic acid. The preparation method of the chemical tracer takes p-chlorofluoromethyl benzene as an initial raw material, and comprises a preparation step of a fluoromethyl benzene Grignard reagent, a preparation step of fluoromethyl benzoate and a preparation step of fluoromethyl benzoic acid. The invention further provides application of p-fluoromethyl benzoic acid as a chemical tracer in oil exploitation, trace detection can be realized, and the detection precision is improved.