19372-00-0

Basic information

• Product Name: trimethyl-[(E)-2-phenylethenyl]silane
• Synonyms: trimethyl-[(E)-2-phenylethenyl]silane;(E)-1-(Trimethylsilyl)-2-phenylethene;(E)-β-(Trimethylsilyl)styrene;[(E)-2-(Trimethylsilyl)vinyl]benzene;[(E)-Styryl]trimethylsilane;Trimethyl[(E)-styryl]silane
• CAS NO: 19372-00-0
• Molecular Formula: C₁₁H₁₆Si
• Molecular Weight: 176.33
• Mol File: 19372-00-0.mol
• Article Data: 93

Chemical Properties

• Melting Point: 20-21 °C
• Boiling Point: 214.1°Cat760mmHg
• Flash Point: 68.7°C
• Appearance: /
• Density: 0.885g/cm³
• Vapor Pressure: 0.231mmHg at 25°C
• Refractive Index: 1.515
• CAS DataBase Reference: trimethyl-[(E)-2-phenylethenyl]silane(CAS DataBase Reference)
• NIST Chemistry Reference: trimethyl-[(E)-2-phenylethenyl]silane(19372-00-0)
• EPA Substance Registry System: trimethyl-[(E)-2-phenylethenyl]silane(19372-00-0)

Safety Data

• Hazardous Substances Data: 19372-00-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C11H16Si/c1-12(2,3)10-9-11-7-5-4-6-8-11/h4-10H,1-3H3/b10-9+

Upstream product

• 3412-59-7 (E)-1-phenyl-2-trichlorosilylethene 
• 75-16-1 methylmagnesium bromide 
• 58541-13-2 Phenyl-carbamic acid 1-phenyl-2-trimethylsilanyl-ethyl ester 
• 1066-35-9 dimethylmonochlorosilane 
• 536-74-3 phenylacetylene 
• 2170-06-1 1-Phenyl-2-(trimethylsilyl)acetylene 
• 100-42-5 styrene 
• 993-07-7 trimethylsilan 
• 16029-98-4 trimethylsilyl iodide 
• 5616-55-7 2-phenyl-1,3-dithiane 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 108-86-1 bromobenzene 
• 109297-56-5 trans-1-(9-borabicyclo<3.3.1>non-9-yl)-2-(trimethylsilyl)ethene 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 

Downstream Products

• 67154-89-6 trans-N,N-Bis(trimethylsilyl)aminostyrol 
• 772-64-5 (phenylethyl)silane 
• 41115-15-5 1,4-Diphenyl-2,3-bis-(trimethylsilyl)-butan 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 80253-15-2 1-phenyl-4-chloro-4-methyl-(E)-1-pentene 
• 112068-21-0 rac-(E)-2-hydroxy-4-phenyl-3-butenoic acid methyl ester 
• 530-48-3 1,1-Diphenylethylene 
• 588-59-0 stilbene 
• 51318-07-1 1,1-diphenyl-2-trimethylsilylethene 
• 57266-94-1 (Z)-(1,2-diphenylvinyl)-trimethylsilane 
• 57266-93-0 ((E)-1,2-diphenylvinyl)trimethylsilane 
• 70624-80-5 1-[(1E)-2-phenylethenyl]-tricyclo[3.3.1.1^3,7]decane 
• 59556-86-4 2-Phenyl-3-(trimethylsilyl)-propanal 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 

Relevant articles and documents

TRANS-VINYLSILANES VIA SUZUKI-MIYAURA COUPLING

Representative aryl, vinyl and alkynyl bromides undergo efficient Pd-catalyzed cross coupling with trans-1-(9-borabicyclonon-9-yl)-2-(trimethylsilyl)ethene (1) under basic conditions to produce the corresponding trans styryl-, dienyl- and enynylsilanes (58-89percent).

A New Elimination-Rearrangement Involving Silicon Migration

Lithium diisopropylamide (LDA), a strongly basic, poorly silicophilic nucleophile reacts with α-phenylsilanes bearing β-leaving groups to cause 1,2-silyl migration and loss of the leaving group.

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

An Annelated Mesoionic Carbene (MIC) Based Ru(II) Catalyst for Chemo- And Stereoselective Semihydrogenation of Internal and Terminal Alkynes

The catalytic utility of [RuL1(CO)2I2] (1), containing an annelated π-conjugated imidazo-naphthyridine-based mesoionic carbene (MIC) ligand (L1), is evaluated for E-selective alkyne semihydrogenation. The precatalyst 1, in combination with 2 equiv of AgBArF, semihydrogenates a broad range of internal alkynes with molecular hydrogen (5 bar) in water. (E)-Alkenes are accessed in high yields, and a number of reducible functional groups are tolerated. A chelate MIC ligand and two cis carbonyls provide a well-defined platform at the Ru center for hydrogenation and isomerization. The loss of two iodides and the presence of two carbonyls render the Ru center electron deficient and thus the formation of metal vinylidenes with terminal alkynes is avoided. This is leveraged for the semihydrogenation of terminal alkynes by the same catalytic system in isopropyl alcohol. Reaction profile, isomerization, kinetic, and DFT studies reveal initial alkyne hydrogenation to a (Z)-alkene, which further isomerizes to an (E)-alkene via metal-catalyzed Z → E isomerization.