78808-66-9

Basic information

• Product Name: α,α-d₂-benzyltrimethylsilane
• Synonyms: α,α-d₂-benzyltrimethylsilane
• CAS NO: 78808-66-9
• Molecular Weight: 166.307
• Mol File: 78808-66-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: α,α-d₂-benzyltrimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: α,α-d₂-benzyltrimethylsilane(78808-66-9)
• EPA Substance Registry System: α,α-d₂-benzyltrimethylsilane(78808-66-9)

Safety Data

• Hazardous Substances Data: 78808-66-9(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 33712-34-4 benzyl-d2 chloride 
• 51271-29-5 [1',1'-2H₂]benzyl bromide 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 935-66-0 phenylacetonitrile-α,α-d2 
• 21175-64-4 1,1-dideuteriophenylmethanol 

Relevant articles and documents

SET and exciplex pathways in the photochemical reactions between aromatic ketones and benzylsilane and stannane derivatives

The photochemical reaction of α,α,α-trifluoroacetophenone (TFA), benzophenone, and p-cyanoacetophenone with benzyltrimethylsilane in MeCN involves hydrogen transfer from the benzylic position. Desilylation occurs as a minor process only in the case of TFA (but it increases greatly in the presence of MeOH or LiClCO4). The final products result from the statistical recombination of the benzyl and ketyl radicals. Further cases of intramolecular selectivity studied are p-methylbenzyl- and p-methoxybenzyltrimethylsilane (the latter substrate undergoes mainly C-Si bond cleavage in the reaction with TFA) as well as benzyltributylstannane (only destannylation observed with all ketones). Product studies are complemented by the determination of relevant kinetic parameters through steadystate and flash-photolysis experiments. The results are explained in terms of hydrogen transfer proceeding from an exciplex and desilylation from the solvent separated radial ion pair. The latter species predominates when ΔGet -1.

Rhodium-catalyzed silylation and intramolecular arylation of nitriles via the silicon-assisted cleavage of carbon-cyano bonds

A rhodium-catalyzed silylation reaction of carbon - cyano bonds using disilane has been developed. Under these catalytic conditions, carbon-cyano bonds in aryl, alkenyl, allyl, and benzyl cyanides bearing a variety of functional groups can be silylated. The observation of an enamine side product in the silylation of benzyl cyanides and related stoichiometric studies indicate that the carbon-cyano bond cleavage proceeds through the deinsertion of silyl isocyanide from η2-iminoacyl complex B. Knowledge gained from these studies has led to the development of a new intramolecular biaryl coupling reaction in which aryl cyanides and aryl chlorides are cross-coupled.