5736-46-9

Usage

Uses

Used in Organic Synthesis:
Bis(pentafluorophenyl)methane is used as a building block in organic synthesis for its strong electron-withdrawing properties, which are attributed to the presence of fluorine atoms. This characteristic makes it useful in the preparation of highly reactive intermediates.
Used in Material Production:
In the production of materials, Bis(pentafluorophenyl)methane is utilized in the creation of polymers and pharmaceuticals, taking advantage of its unique chemical properties to enhance the performance of these products.
Used in Organic Electronics:
Bis(pentafluorophenyl)methane has potential applications in the field of organic electronics, where its properties can contribute to the development of advanced electronic devices and components.
Used as a Semiconductor Stabilizer:
Additionally, Bis(pentafluorophenyl)methane serves as a stabilizer in the semiconductor industry, where its strong electron-withdrawing nature can improve the stability and performance of semiconductor materials.
It is crucial to handle Bis(pentafluorophenyl)methane with care, as its strong reactivity and potential toxicity can pose health and environmental hazards if not properly managed.

Upstream product

• 52438-80-9 Decafluoro-diphenyl-acetaldehyd 
• 853-39-4 bis(pentafluorophenyl)-methanone 
• 776-76-1 methyldiphenylsilane 
• 1109-15-5 tris(pentafluorophenyl)borate 
• 766-77-8 Dimethylphenylsilane 
• 16307-66-7 Bis--carbonium 
• 6485-79-6 chlorotriisopropylsilane 
• 617-86-7 triethylsilane 
• 1438-82-0 1,1,1,3,3-pentamethyl-1,3-disiloxane 
• 151798-54-8 Ethyl N-nitroso-N-carbamate 
• 5736-48-1 bis(pentafluorophenyl)methyl chloride 
• 1766-76-3 decafluorobenzhydrol 
• 363-72-4 Pentafluorobenzene 
• 832-72-4 2,3,4,5,6-pentafluorophenylacetyl chloride 

Downstream Products

• 5736-52-7 Bis(3,4,6-trifluor-2,5-dioxo-3,6-cyclohexadien-1-yl)methan 
• 5736-53-8 3,4,6-Trifluoro-2,5-dioxo-3,6-cyclohexadien-1-yl-pentafluorphenylmethan 

Relevant academic research and scientific papers

Kinetic hydricity of silane hydrides in the gas phase

Herein, gas phase studies of the kinetic hydricity of a series of silane hydrides are described. An understanding of hydricity is important as hydride reactions figure largely in many processes, including organic synthesis, photoelectrocatalysis, and hydrogen activation. We find that hydricity trends in the gas phase differ from those in solution, revealing the effect of solvent. Calculations and further experiments, including H/D studies, were used to delve into the reactivity and structure of the reactants. These studies also represent a first step toward systematically understanding nucleophilicity and electrophilicity in the absence of solvent.

Transition-Metal-Free Cleavage of CO

Tertiary silane 1H, 2-[(diphenylsilyl)methyl]-6-methylpyridine, reacts with tris(pentafluorophenyl)borane (BCF) to form the intramolecular pyridine-stabilized silylium 1+-HBCF. The corresponding 2-[(diphenylsilyl)methyl]pyridine, lacking the methyl-group on the pyridine ring, forms classic N(py)→B adduct 2H-BCF featuring an intact silane Si?H fragment. Complex 1+-HBCF promotes cleavage of the C≡O triple bond in carbon monoxide with double C?Csp2 bond formation, leading to complex 3 featuring a B-(diarylmethyl)-B-aryl-boryloxysilane fragment. Reaction with pinacol generates bis(pentafluorophenyl)methane 4 as isolable product, proving the transition-metal-free deoxygenation of carbon monoxide by this main-group system. Experimental data and DFT calculations support the existence of an equilibrium between the silylium–hydroborate ion pair and the silane–borane mixture that is responsible for the observed reactivity.

Generation, Reactions, Direct Observation, and Kinetics of Decafluorodiphenylcarbene

Bis(pentafluorophenyl)diazomethane (1a) was prepared, and reactivities of perfluorodiphenylcarbene (2a) generated by photolysis of 1a were investigated not only in terms of product analysis but also by using matrix isolation spectroscopy as well as laser flash photolysis techniques.Product distributions observed in the reactions of 2a in benzene, cyclohexane, and trans-1,2-dichloroethylene suggested that 2a reacted with those substrates with moderate reactivities toward carbene mostly in its singlet state presumably owing to the increased electrophilicity induced by fluorine substituents while the reaction with the alkane C-H bonds in concerted fashion was retarded partly due to steric effect in the singlet state which thus decayed to the triplet states that underwent predominantly H atom abstraction forming tetraarylethane.Photolysis of 1a in Ar matrix at 10 K produced 2a which was observed by IR and UV and shown to react with doped O2 to produce ultimately perfluorobenzoate by way of the carbonyl oxide and dioxirane, both intermediates being characterized by IR and UV/vis spectroscopy.Laser flash photolysis of 1a in acetonitrile solution produced a transient absorption (λ = 320 nm) due to bis(pentafluorophenyl)methyl radical (14a) obviously produced by H atom abstraction of the triplet 2a, which was trapped by oxygen to generate the carbonyl oxide (11a) showing its absorption maximum at 400 nm (τ = 5 ms) and also by 1,4-cyclohexadiene to form the methyl radical (14a) with the rate constant of 1.1E7 M-1 s-1.The lifetime of the triplet 2a was estimated to be ca. 1 μs.