2443-45-0

Usage

Physical state

Clear, viscous liquid

Usage

Crosslinking agent in dental composites and sealants

Known for

High strength and durability

Popularity

Widely used in dental restorations

Health concerns

Potential endocrine disruption and other adverse health effects

Current status

Ongoing research to understand potential risks

Upstream product

• 611-94-9 4-Methoxybenzophenone 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 64-17-5 ethanol 

Downstream Products

• 103281-33-0 2,2-bis-(p-methoxyphenyl)-1,2-diphenylethanone 
• 103098-60-8 2,2-bis-(4-methoxy-phenyl)-1,2-diphenyl-ethanol 

Relevant academic research and scientific papers

Iron-catalyzed pinacol coupling of aryl ketones with a phenyltitanium reagent: A new type of catalytic reaction

A reaction of aryl ketones with phenyltitanium triisopropoxide ([PhTi(Oi-Pr)3]) in the presence of [Fe(acac)3] as a catalyst (1 mol%) gave the corresponding pinacols in high yields. The catalytic cycle of this process involves an iron-catalyzed disproportionation of [PhTi(Oi-Pr) 3] into biphenyl and a lowvalent titanium species.

InCl3/Al mediated pinacol coupling reactions of aldehydes and?ketones in aqueous media

A systematic work on the homo-pinacol coupling reactions of benzophenones, aldehydes, and acetophenones in aqueous media with InCl3/Al is described for the first time, in which various 1,2-diols are obtained in moderate to good yields.

Photoreduction of benzophenones by amines in room-temperature ionic liquids

(equation presented) The amine-mediated photoreduction of benzophenones in room temperature ionic liquids was investigated. Unlike the analogous reaction in organic solvents, the photoreduction produces mainly the corresponding benzhydrol in most cases. Because the reaction consumes only 1 equiv of amine and the solvent can be easily recycled, the photoreduction allows a very clean method for the conversion of benzophenones to benzhydrols.

A novel method for pinacolic coupling of aromatic aldehydes and ketones with a Sm-ZnCl2 system

Sm-ZnCl2-system-mediated reductive coupling of aromatic aldehydes and ketones in THF-H2O at room temperature affords the corresponding pinacols in moderate to good yields.

Direct measurement of ultrafast carbon-carbon cleavage rates via the subpicosecond charge-transfer activation of pinacols

Highly transient (benzpinacol) cation radicals (D2+.) and their ultrafast mesolytic fragmentations to the diarylhydroxymethyl radical (D.) and cation (D+) are directly observed on the early picosecond time scale upon the charge-transfer photoactivation of the intermolecular donor-acceptor complexes of pinacol donors with methyl viologen. Ultrashort lifetimes of the cation radicals with τ ~ 10 ps obtain (for the first time) from quantitative kinetics analysis of the time-resolved spectroscopic results. These rapid C-C bond scissions successfully compete with back-electron transfer, which normally predominates on this time scale, and lead to exceptionally high efficiencies for the oxidative fragmentation of pinacols.

2-benzoylbenzoic acid: A photolabile mask for alcohols and thiols

Photolysis of 2-benzoylbenzoate esters of primary and secondary alcohols 1 in the presence of a hydrogen donor (2-isopropanol) or an electron donor (primary amines) produces the corresponding alcohol in high yield. The fate of the benzoate is dependent on the conditions used for the photoreaction. In 2-propanol, the ketyl radical that derives from photoreduction dimerizes, to afford the benzpinacol product 3,3"-diphenylbiphthalidyl, 5. In the presence of amines the product is 3-phenylphthalide, 6, a benzhydrol derivative which is the result of simple reduction of the ketone followed by lactonization. While the photoproduct of the benzoate - 2-propanol reaction results from anticipated free radical chemistry, the amine-promoted reaction appears to result from a second, "dark", electron transfer process. We conclude that 2-benzoylbenzoic acid is an effective photolabile protecting group for primary and secondary alcohols, and preliminary studies indicate that thiols can be protected in an analogous way. Studies on the effect of benzophenone substituents and reaction solvent on the benzhydrol:benzpinacol product ratio provide mechanistic insight into the process.

Surface modification of CdS quantum dots with fluorinated thiophenol

CdS nanocrystallites prepared by capping with pentafluorothiophenol, 2,3,5,6-tetrafluorothiophenol or 4-fluorothiophenol are characterized as quantum dots by TEM, FTIR, NMR, UV-VIS and fluorescence spectroscopy. The crystalline size tends to increase with an increase in the number of fluorine atoms in the capping molecules while maintaining high solubility in organic solvents, with solubility in alcohols depending on the number of fluorine atoms in the capping molecules. Pentafluorophenyl-capped CdS nanocrystallites have the highest solubilities in alcohols, and exhibit quantum dot photocatalysis in methanol, leading to the efficient two-electron transfer photoreduction under visible-light irradiation.

Visible-Light-Induced Two-Electron-Transfer Photoreductions on CdS: Effeects of Morphology

Freshly prepared CdS suspensions (CdS-0) consisting of quantized particles and their loose aggregation catalyze photoreductions of aromatic ketones and olefins in methanol under visible light irradiation using triethylamine as sacrificial electron donor, yielding alcohols and dihydro compounds, respectively, which are more selective than photocatalysis of commercially available crystalline CdS (Aldrich) (CdS-Ald).Deuterium incorporation experiments in photolysis of dimethyl maleate in methanol-O-D revealed that CdS-0 catalyzes sequental two-electron-transfer photoreduction, affording dideuterated dimethyl succinate, while CdS-Ald induces both photoreduction and photoisomerization through disproportionation between one-electron-transfer-reduction intermediates, yielding much trideuterated dimethyl succinate and monodeuterated dimethyl fumarate and maleate.

Novel reduction of carbonyl compounds with Al/NH3/halide under irradiation of ultrasonic wave

Various carbonyl compounds, such as benzophenones and acetophenones, were reduced by Al/NH3/halide under ultrasonic wave irradiation to give the corresponding monohydric alcohols and/or pinacols in satisfactory yields. The addition of inorganic halides improved the selectivity in the formation of monohydric alcohols and pinacols.

Nonmetallised CdS-catalised Photoreduction of Aromatic Ketones to Alcohols and/or Pinacols

In acatonitrile containing triethylamine as a sacrificial electron donor, non-metallized CdS shows photocatalytic activity for reduction of benzophenone derivatives whose reduction potentials are larger than -1.90 V vs. standard calomel electrode (SCE), giving alcohols and/or pinacols under visible light irradiation.