113281-23-5

Basic information

• Product Name: 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(trifluoromethyl)-
• CAS NO: 113281-23-5
• Molecular Formula: C7H5F3O2
• Molecular Weight: 178.111
• Mol File: 113281-23-5.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(trifluoromethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(trifluoromethyl)-(113281-23-5)
• EPA Substance Registry System: 2,5-Cyclohexadien-1-one, 4-hydroxy-4-(trifluoromethyl)-(113281-23-5)

Safety Data

• Hazardous Substances Data: 113281-23-5(Hazardous Substances Data)

Upstream product

• 120120-26-5 (trifluoromethyl)triethylsilane 
• 106-51-4 p-benzoquinone 
• 13636-88-9 3,3-bis(methylthio)-1-phenylprop-2-en-1-one 
• 75-46-7 trifluoromethan 
• 935-50-2 4,4-dimethoxycyclohexa-2,5-dienone 
• 120120-28-7 4-(triethylsiloxy)-4-(trifluoromethyl)-2,5-cyclohexadien-1-one 
• 402-45-9 4-hydroxybenzotrifluoride 

Relevant articles and documents

Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones

The desymmetrization of p-quinols through a chiral bisguanidinium hemisalt catalyzed enantioselective Michael addition/lactonization cascade reaction with azlactones was reported. 3-Amino-benzofuran-2,5-diones containing a chiral amino acid residue were achieved with up to 99% ee and >19?:?1 dr. An exploration of the structure of the catalyst bisguanidinium was undertaken, revealing a bifunctional catalytic model.

Nucleophilic trifluoromethylation of carbonyl compounds and disulfides with trifluoromethane and silicon-containing bases

Provided that DMF (or another N,N-dialkylformamide) is present in the reaction medium, at least in a catalytic amount, fluoroform trifluoromethylates efficiently carbonyl compounds, even enolizable ones, when opposed to (TMS)2N- M+, generated in situ from N(TMS)3 and M+ F- or RO- Na+. When F- is used in a catalytic amount, silylated α-(trifluoromethyl)carbinols are obtained: In this case, the four-component system HCF3/N(TMS)3/catalytic F-/catalytic DMF behaves like the Ruppert's reagent, especially as far as nonenolizable carbonyl compounds are concerned (CF3SiMe3 remains more efficient for enolizable carbonyl compounds). This process involves an adduct between DMF and -CF3 which is the true trifluoromethylating agent. In the same way, fluoroform efficiently trifluoromethylates disulfides and diselenides when deprotonated with a strong base selected from t-BuOK or N(SiMe3)3/Me4NF (or TBAT). t-BuOK is more adapted to the trifluoromethylation of awl disulfides whereas N(SiMe3)3/F- is Well suited to that of aliphatic disulfides.

Gem-disubstituted cyclohexadienones and their production

Quinones may be perfluoroalkylated by means of perfluoroalkyltrihydrocarbyl silane using certain active alkali metal salt catalysts devoid of fluorine (e.g., LiN3, NaN3, KN3, NaCN KCN, CsCN, NaOH, KOH, K2 CO3, and Cs2 CO3). The reaction--which is conducted under essentially anhydrous conditions, preferably in a suitable liquid phase reaction medium, most preferably a dipolar aprotic solvent--results in the formation of gem-disubstituted cyclohexadienones in which the gem substituents are a perfluoroalkyl group and a trihydrocarbylsiloxy group. These gem-disubstituted compounds in turn can be readily converted to perfluoroalkyl substituted aromatics, thus circumventing the traditional need for photochlorination followed by halogen exchange using hydrogen fluoride as a means of preparing perfluoroalkyl aromatic compounds.