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
• Article Data: 133

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

Description

Methyl 4-trifluoromethylbenzoate is an ester that is characterized by its clear colorless to very pale yellow liquid appearance. It has been reported that the reduction of this ester can be catalyzed by MoO2Cl2.

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 
• 329-15-7 4-trifluoromethyl-phenyl acetyl chloride 
• 201230-82-2 carbon monoxide 
• 98-56-6 4-chlorobenzotrifluoride 
• 1126-46-1 Methyl 4-chlorobenzoate 
• 75-63-8 Bromotrifluoromethane 
• 402-43-7 p-trifluoromethylphenyl bromide 
• 155820-05-6 4-(trifluoromethyl)benzyl alcohol methyl ether 
• 922-67-8 propynoic acid methyl ester 
• 455941-77-2 (E)-1-ethoxy-3-trifluoromethyl-1,3-butadiene 
• 455-13-0 4-Iodobenzotrifluoride 

Downstream Products

• 2252-62-2 2-(4-(trifluoromethyl)phenyl)propan-2-ol 
• 112816-01-0 1-<4-(Trifluoromethyl)phenyl>-2-(4-pyrimidinyl)ethenol 
• 73100-66-0 2-(2-Quinoxalyl)-1-(4-trifluoromethylphenyl)ethanone 
• 98-86-2 acetophenone 
• 131089-02-6 α,α-<2H2>p-trifluoromethylbenzyl alcohol 
• 73790-20-2 4,4'-bis(trifluoromethyl)benzil 
• 85957-45-5 1-(4-(Trifluoromethyl)phenyl)-2-(4(1H)-quinazolinylidene)ethanone 
• 71682-94-5 ω-cyano-4-trifluoromethylacetophenone 
• 164594-47-2 3-Hydroxy-1-methyl-3-(4-trifluoromethyl-phenyl)-azetidine-2-thione 
• 339-59-3 4-(trifluoromethyl)benzoic acid hydrazide 
• 99-75-2 4-methyl-benzoic acid methyl ester 
• 196934-20-0 4-(trifluoromethyl)benzoic acid t-butyl ester 
• 79-20-9 acetic acid methyl ester 
• 53790-08-2 N-(2-hydroxyethyl)-4-(trifluoromethyl)benzamide 

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.

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.

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.

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.