1694-23-1

Upstream product

• 92-52-4 biphenyl 
• 107-06-2 1,2-dichloro-ethane 
• 644-08-6 4-Methylbiphenyl 
• 1667-11-4 biphenyl-4-methylchloride 
• 4939-76-8 4-Phenyl-benzyl 
• 4746-80-9 4,4'-diphenylbenzil 
• 10034-85-2 hydrogen iodide 
• 29263-69-2 4-(phenoxymethyl)-1,1'-biphenyl 
• 930-69-8 sodium thiophenolate 
• 2567-29-5 p-phenylbenzyl bromide 
• 110-82-7 cyclohexane 
• 84648-91-9 biphenyl-4-yldiazomethane 
• 3218-36-8 4-Phenylbenzaldehyde 
• 541-41-3 chloroformic acid ethyl ester 

Downstream Products

• 644-08-6 4-Methylbiphenyl 
• 100-21-0 terephthalic acid 

Relevant academic research and scientific papers

(1-Selenocyanatoethyl)benzene: A Selenocyanation Reagent for Site-Selective Selenocyanation of Inert Alkyl C(sp3)-H Bonds

A new, simple, yet easily accessible, (1-selenocyanatoethyl)benzene has been designed and applied as a SeCN group transfer reagent for selenocyanation of aliphatic C(sp3)-H bonds for the first time. This protocol is featured with mild reaction conditions and wide substrate scope. Control experiments reveal that a radical-group transfer mechanism might be involved.

Heterogeneous photocatalytic C-C coupling: Mechanism of plasmon-mediated reductive dimerization of benzyl bromides by supported gold nanoparticles

The use of gold nanoparticles supported on TiO2 (Au@TiO2) as photocatalysts was extended to include photoinduced reductive C-C coupling. Surface plasmon excitation of supported AuNPs in the presence of an amine leads to the C-C coupling of a variety of substituted benzyl bromides at room temperature with good yields in a free radical-mediated reaction. The overall efficiency of the C-C coupling is largely dependent on the nature of the amine used.

Straightforward synthesis of substituted dibenzyl derivatives

The C-C bond formation by homogeneous catalysis is a powerful tool in organic synthesis. The replacement of noble metal by cheaper one for already reported methodologies is of interest for an economical purpose. The attractivity of such replacement is also enhanced if a first raw transition metal is found to be active in several processes. This work demonstrates that a common nickel complex can be used for a two-step cross-coupling procedure, namely a homocoupling reaction of benzyl derivatives and a subsequent Suzuki reaction. These consecutive reactions permit the synthesis of new polyfunctionalized dibenzyl compounds.

Ultrafast study of p-biphenylyldiazomethane and p-biphenylylcarbene

p-Biphenylyldiazomethane was excited by femtosecond pulses of UV light in acetonitrile, in cyclohexane, and in methanol. Ultrafast photolysis produces a singlet excited state of p-biphenylyldiazomethane with λmax = 490 nm, and lifetimes of less than 300 fs in acetonitrile, in cyclohexane, and in methanol. The decay of the excited state is accompanied by the growth of transient absorption with λmax = 360 nm. The carrier of this transient absorption is attributed to singlet p-biphenylylcarbene, a result that is consistent with the predictions of TD-DFT calculations. The singlet carbene lifetimes are 200 and 77 ps in acetonitrile and cyclohexane, respectively, and are controlled by intersystem crossing to the lower energy triplet state. The transient absorption does not decay to baseline in acetonitrile, because of the formation of nitrile ylide. The equilibrium mixture of singlet and triplet p-biphenylylcarbene reacts with acetonitrile to form a nitrile ylide (λmax = 370 nm), and with cyclohexane by C-H insertion 1-20 ns after the laser pulse. The singlet carbene lifetime is only 7.9 ps in methanol, owing to a rapid reaction with the solvent. Reaction with the solvent gives rise, in part, to a p-biphenylylbenzyl cation (λmax = 450 nm, τ = 6.3 ps) in methanol.

Fragmentation of anion radicals with elimination of aryloxy groups

4-Vinylbenzyl phenyl ether, 4-phenylbenzyl phenyl ether, 1- and 2-naphthylmethyl phenyl ethers react with sodium thiophenolate under photochemical stimulation with replacement of the phenoxy group. The composition of reaction products and relation of reactivity to the structure of substrates is consistent with anion-radical mechanism. The corresponding methoxy and cyano derivatives do not undergo the reaction.

Mechanism and reactivity parameters of the reduction of arylmethyl radicals from time-resolved electron-photoinjection experiments

The 9-anthrylmethyl, diphenylmethyl, benzyl, and 4-methylbenzyl radicals are generated by reduction of the corresponding chlorides with electrons photoinjected in laser pulse experiments. The 'polarograms' derived from the variation of the charge flowing through the electrode with the dc potential of the electrode represent the reduction of these radicals to the corresponding anions. The meaning of the half-wave potentials is investigated through their variations with the measurement time and with the addition of acids in the solution, which accelerates the disappearance of the carbanion. Correcting the kinetic data for the effect of radical dimerization, the reduction kinetics appear to be mostly under the control of the follow-up reaction of the carbanion with acids present in the medium, although the effect of charge-transfer kinetics begins to interfere at the lower end of the time window. The results are compared with earlier data obtained by other techniques. The changes in reactivity observed in the series are discussed with the help of density functional quantum chemical calculations.

Multiple-photon ? chemistry in the laser-jet: Photochemistry of the 4-biphenylmethyl radical

In laser-jet (LJ) photolysis (high intensity) of the ether 4-(4-benzoylphenoxymethyl)biphenyl 1 a two-photon process is observed in CCl4 to yield 4-(chloromethyl)biphenyl 5 as product (3%), while the one-photon product is 4-biphenylaldehyde 7 (100% in conventional photolysis versus 97% in laser-jet photolysis). In ethanol, the results suggest a three-proton reaction in which 4-(ethoxymethyl)biphenyl 6 is produced in appreciable amounts (18%) in addition to the one-photon product 1,2-bis(4-biphenyl)ethane 4, the latter as the major product (82%). It is proposed that under high-intensity LJ photolysis conditions the electronically-excited 4-biphenylmethyl radical 2* is photoionized to the 4-biphenylmethyl cation 2+ and that the latter is trapped by ethanol to give the 4-biphenylmethyl ether 6.