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.

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.

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.