393-40-8

Basic information

• Product Name: 2-(trifluoromethyl)-1,4-benzoquinone
• Synonyms: 2-(Trifluoromethyl)-1,4-benzoquinone; 2,5-cyclohexadiene-1,4-dione, 2-(trifluoromethyl)-
• CAS NO: 393-40-8
• Molecular Formula: C₇H₃F₃O₂
• Molecular Weight: 176.09
• Mol File: 393-40-8.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 133.2°C at 760 mmHg
• Flash Point: 34.3°C
• Density: 1.503g/cm³
• Vapor Pressure: 8.54mmHg at 25°C
• Refractive Index: 1.457
• CAS DataBase Reference: 2-(trifluoromethyl)-1,4-benzoquinone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(trifluoromethyl)-1,4-benzoquinone(393-40-8)
• EPA Substance Registry System: 2-(trifluoromethyl)-1,4-benzoquinone(393-40-8)

Safety Data

• Hazardous Substances Data: 393-40-8(Hazardous Substances Data)

Usage

Quinone derivative

A class of organic compounds that are often used as oxidation-reduction agents and have various industrial applications.

Trifluoromethyl group

A unique functional group present in the compound, which can exhibit special chemical reactivity and is often utilized in the synthesis of pharmaceuticals and agrochemicals.

Electron acceptor

2-(trifluoromethyl)-1,4-benzoquinone has been studied for its potential as an electron acceptor in organic electronic devices, which can be useful in the development of new technologies.

Catalyst

The compound has also been researched for its potential use as a catalyst in organic reactions, which can help improve the efficiency and effectiveness of certain chemical processes.

Hazardous if not properly managed

It is important to handle 2-(trifluoromethyl)-1,4-benzoquinone with caution, as it may pose risks to human health and the environment if not properly stored or disposed of.

Upstream product

• 98-17-9 3-Trifluoromethylphenol 
• 887144-94-7 Togni's reagent II 
• 2237-14-1 1,4-benzoquinone-d4 
• 106-51-4 p-benzoquinone 
• 445-04-5 4-amino-3-(trifluoromethyl)-phenol 
• 887144-97-0 Togni's reagent 
• 88-30-2 3-trifluoromethyl-4-nitrophenol 

Downstream Products

• 16052-53-2 2-chloro-3-(trifluoromethyl)-1,4-benzoquinone 
• 16052-52-1 trans-3-Ethylamino-2-(α,α,α-trifluor-2,5-dihydroxy-o-tolyl)-crotonsaeure-ethylester 
• 197858-76-7 4',5'-Dibromo-3',6'-dioxo-2'-trifluoromethyl-bicyclohexyl-1',4'-diene-4-carboxylic acid methyl ester 
• 197859-04-4 4',5'-Dibromo-3',6'-dioxo-2'-trifluoromethyl-bicyclohexyl-1',4'-diene-4-carboxylic acid methyl ester 
• 197858-66-5 2,3-Dibromo-5-trifluoromethyl-benzene-1,4-diol 
• 197858-57-4 2,3-Dibromo-5-trifluoromethyl-[1,4]benzoquinone 
• 16052-87-2 2-Chlor-3-trifluormethyl-hydrochinon 

Relevant articles and documents

A scalable Nenitzescu synthesis of 2-methyl-4-(trifluoromethyl)-1H-indole- 5-carbonitrile

2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a key intermediate in the synthesis of selective androgen receptor modulators discovered in these laboratories. A practical and convergent synthesis of the title compound starting from 4-nitro-3-(tr

Effects of B2pin2 and PCy3 on copper-catalyzed trifluoromethylation of substituted alkenes and alkynes with the Togni reagent

The copper-catalyzed oxytrifluoromethylation of phenylacetylenes and C-H trifluoromethylation of quinones were studied. It was found that both reactions are accelerated by B2pin2 and PCy3 additives. The two reactions have different substituent effects. The oxytrifluoromethylation is faster in the presence of electron-donating groups, while the C-H trifluoromethylation is faster with electron-withdrawing substituents. The Hammett plot for oxytrifluoromethylation gave a ρ value of -0.76 indicating electron demand in the rate determining step of the reaction. According to the absolute value of ρ the reaction probably does not proceed through a rate determining formation of a carbocation intermediate. The kinetic isotope effect measurements indicate that in C-H trifluoromethylation of quinones the cleavage of the C-H bond is not the rate determining step of the reaction.

Copper-catalyzed direct C-H trifluoromethylation of quinones

An efficient and practical methodology has been developed to introduce the CF3 group onto quinones through Cu(I)-catalyzed direct C-H trifluoromethylation of quinones.