64788-85-8

Basic information

• Product Name: Silane, dimethylphenyl[(1E)-2-phenylethenyl]-
• CAS NO: 64788-85-8
• Molecular Formula: C16H18Si
• Molecular Weight: 238.404
• Mol File: 64788-85-8.mol

Chemical Properties

• CAS DataBase Reference: Silane, dimethylphenyl[(1E)-2-phenylethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, dimethylphenyl[(1E)-2-phenylethenyl]-(64788-85-8)
• EPA Substance Registry System: Silane, dimethylphenyl[(1E)-2-phenylethenyl]-(64788-85-8)

Safety Data

• Hazardous Substances Data: 64788-85-8(Hazardous Substances Data)

Upstream product

• 15436-06-3 (E)-β-(methylthio)styrene 
• 79628-15-2 dimethyl(phenyl)(phenylethynyl)silane 
• 5272-18-4 dimethylphenylsilanol 
• 1125-26-4 dimethylphenylvinylsilane 
• 768-33-2 phenyldimethylsilyl chloride 
• 591-50-4 iodobenzene 
• 1178871-13-0 (E)-1-[diethoxy(methyl)silyl]-2-[dimethyl(phenyl)silyl]ethylene 
• 3839-31-4 dimethyl(phenyl)silyl lithium 
• 795-47-1 (E)-diphenyl(styryl)phosphine oxide 
• 1261157-96-3 [2-(dimethylphenylsilyl)-2-phenylethyl]diphenylphosphane oxide 
• 766-77-8 Dimethylphenylsilane 
• 536-74-3 phenylacetylene 
• 64788-84-7 β-(Z)-2-dimethylphenylsilylstyrene 
• 100-52-7 benzaldehyde 

Downstream Products

• 841-18-9 (E)-1-(4-acetamidophenyl)-2-phenylethene 
• 59873-86-8 (E)-4-methyl-1-phenylpenta-1,4-dien-3-one 
• 3988-77-0 2-cinnamoylthiophene 
• 3160-32-5 (1E)-4-methyl-1-phenylpent-1-en-3-one 
• 538-44-3 (E)-benzylidenepinacolone 
• 84642-43-3 (E)-1-phenylhepta-1,6-dien-3-one 
• 3152-68-9 (1E)-1-phenylpent-1-en-3-one 
• 614-47-1 1,3-diphenyl-propen-3-one 
• 22966-19-4 trans-4'-methoxychalcone 
• 200010-90-8 dimethyl(phenyl)[2-phenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl]silane 
• 1440972-07-5 (R)-dimethyl(phenyl)(2-phenyl-1-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)ethyl)silane 
• 138492-00-9 4α-hydroxy-1-methyl-2β-(1-methylethyl)-3β-phenylpyrrolidine 
• 1896-62-4 (E)-benzalacetone 
• 56-33-7 1,1,3,3-tetramethyl-1,3-diphenyldisiloxane 

Relevant articles and documents

Silsesquioxyl rhodium(i) complexes - Synthesis, structure and catalytic activity

The first bi- and mononuclear rhodium(i) complexes [{Rh(μ-OSi 8O12(i-Bu)7)(cod)}2] (5), [Rh(cod)(PCy3)(OSi8O12(i-Bu)7)] (6) with a hindered hepta(iso-butyl)silsesquiox

The two faces of platinum hydrospirophosphorane complexes—Not only relevant catalysts but cytotoxic compounds as well

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Caged Iridium Catalyst for Hydrosilylation of Alkynes with High Site Selectivity

The proximity and orientation of the reacting groups can be different in organic cages from in free solution, thus affecting the selectivity of the reaction. Herein, we reported a synthetic strategy to encapsulate iridium nanoparticles (Ir-NP@COP1-T) within organic cages in the homogeneous solution. Ir-NP@COP1-T showed good selectivity in the hydrosilylation reaction of alkynes. Our work provides a new perspective to the catalysis field by using soluble microporous cages as support for inorganic nano particles.

Asymmetric Hydrosilylation of β-Silyl Styrenes Catalyzed by a Chiral Palladium Complex

A palladium complex coordinated with a chiral SIPHOS ligand was evaluated as an efficient catalyst for asymmetric hydrosilylation of β-silyl styrenes with trichlorosilane and 23 1,2-bis(silyl) chiral compounds were produced. Good to excellent enantioselec

Rh(I)/(III)-N-Heterocyclic Carbene Complexes: Effect of Steric Confinement Upon Immobilization on Regio- and Stereoselectivity in the Hydrosilylation of Alkynes

Rh(I) NHC and Rh(III) Cp* NHC complexes (Cp=pentamethylcyclopentadienyl, NHC=N-heterocyclic carbene=pyrid-2-ylimidazol-2-ylidene (Py?Im), thiophen-2-ylimidazol-2-ylidene) are presented. Selected catalysts were selectively immobilized inside the mesopores

Iridium(i) complexes bearing hemilabile coumarin-functionalised N-heterocyclic carbene ligands with application as alkyne hydrosilylation catalysts

A set of iridium(i) complexes of formula IrCl(κC,η2-IRCouR′)(cod) or IrCl(κC, η2-BzIRCouR′)(cod) (cod = 1,5-cyclooctadiene; Cou = coumarin; I = imidazolin-2-carbene; BzI = benzimidazolin-2-carbene) have beeen prepared from the corresponding azolium salt and [Ir(μ-OMe)(cod)]2 in THF at room temperature. The crystalline structures of 4b and 5b show a distorted trigonal bipyramidal configuration in the solid state with a coordinated coumarin moiety. In contrast, an equilibrium between this pentacoordinated structure and the related square planar isomer is observed in solution as a consequence of the hemilability of the pyrone ring. Characterization of both species by NMR was achieved at the low and high temperature limits, respectively. In addition, the thermodynamic parameters of the equilibrium, ΔHR and ΔSR, were obtained by VT 1H NMR spectroscopy and fall in the range 22-33 kJ mol-1 and 72-113 J mol-1 K-1, respectively. Carbonylation of IrCl(κC,η2-BzITolCou7,8-Me2)(cod) resulted in the formation of a bis-CO derivative showing no hemilabile behaviour. The newly synthesised complexes efficiently catalyze the hydrosilylation of alkynes at room temperature with a preference for the β-(Z) vinylsilane isomer.

Manganese-Catalyzed Dehydrogenative Silylation of Alkenes following Two Parallel Inner-Sphere Pathways

We report on an additive-free Mn(I)-catalyzed dehydrogenative silylation of terminal alkenes. The most active precatalyst is the bench-stable alkyl bisphosphine Mn(I) complex fac-[Mn(dippe)(CO)3(CH2CH2CH3)]. The catalytic process is initiated by migratory insertion of a CO ligand into the Mn-alkyl bond to yield an acyl intermediate which undergoes rapid Si-H bond cleavage of the silane HSiR3 forming the active 16e- Mn(I) silyl catalyst [Mn(dippe)(CO)2(SiR3)] together with liberated butanal. A broad variety of aromatic and aliphatic alkenes was efficiently and selectively converted into E-vinylsilanes and allylsilanes, respectively, at room temperature. Mechanistic insights are provided based on experimental data and DFT calculations revealing that two parallel reaction pathways are operative: an acceptorless reaction pathway involving dihydrogen release and a pathway requiring an alkene as sacrificial hydrogen acceptor.

Continuous-flow Si-H functionalizations of hydrosilanesviasequential organolithium reactions catalyzed by potassiumtert-butoxide

We herein report an atom-economic flow approach to the selective and sequential mono-, di-, and tri-functionalizations of unactivated hydrosilanesviaserial organolithium reactions catalyzed by earth-abundant metal compounds. Based on the screening of various additives, we found that catalytic potassiumtert-butoxide (t-BuOK) facilitates the rapid reaction of organolithiums with hydrosilanes. Using a flow microreactor system, various organolithiums bearing functional groups were efficiently generatedin situunder mild conditions and consecutively reacted with hydrosilanes in the presence oft-BuOK within 1 min. We also successfully conducted the di-funtionalizations of dihydrosilane by sequential organolithium reactions, extending to a gram-scale-synthesis. Finally, the combinatorial functionalizations of trihydrosilane were achieved to give every conceivable combination of tetrasubstituted organosilane libraries based on a precise reaction control using an integrated one-flow system.

Copper-Photocatalyzed Hydrosilylation of Alkynes and Alkenes under Continuous Flow

Herein, the photocatalytic hydrosilylation of alkynes and alkenes under continuous flow conditions is described. By using 0.2 mol % of the developed [Cu(dmp)(XantphosTEPD)]PF6 under blue LEDs irradiation, a large panel of alkenes and alkynes was hydrosilylated in good to excellent yields with a large functional group tolerance. The mechanism of the reaction was studied, and a plausible scenario was suggested.

Direct Access to α,β-Unsaturated Ketones via Rh/MgCl2-Mediated Acylation of Vinylsilanes

We report herein the facile and practical construction of α,β-unsaturated ketones via rhodium-catalyzed direct acylation of vinylsilanes with readily available and abundant carboxylic acids. This protocol features access to a diverse array of synthetically useful functionalities with moderate to excellent yields. More importantly, the late-stage functionalization of pharmaceuticals was also realized with synthetically useful yield.