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

• 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 
• 13683-41-5 1-bromo-1-(trimethylsilyl)ethene 
• 38111-44-3 phenylzinc(II) bromide 
• 61244-94-8 α-styrylpentamethyldisilane 
• 40595-36-6 β-styrylpentamethyldisilane 
• 2612-42-2 (dibromomethyl)trimethylsilane 
• 100-52-7 benzaldehyde 
• 2117-28-4 bis(trimethylsilyl)methane 
• 5180-93-8 (methoxydimethylsilyl)(trimethylsilyl)methane 
• 2344-80-1 Chloromethyltrimethylsilane 
• 41309-43-7 (2-bromovinyl)trimethylsilane 

Downstream Products

• 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 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 57266-93-0 ((E)-1,2-diphenylvinyl)trimethylsilane 
• 70624-80-5 1-[(1E)-2-phenylethenyl]-tricyclo[3.3.1.1^3,7]decane 
• 886-65-7 trans,trans-1,4-Diphenyl-1,3-butadiene 
• 99948-26-2 (4S,5R)-2-Methyl-3,5-diphenyl-4-trimethylsilanyl-isoxazolidine 
• 124306-24-7 r-1-chloro-t-3-phenyl-c-2-trimethylsilyl-cyclopropyl phenyl sulfide 
• 124306-24-7 r-1-chloro-c-3-phenyl-t-2-trimethylsilyl-cyclopropyl phenyl sulfide 
• 36195-58-1 (E)-1-phenyl-3-phenylthio-1-butene 

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

Divergent Synthesis of Vinyl-, Benzyl-, and Borylsilanes: Aryl to Alkyl 1,5-Palladium Migration/Coupling Sequences

Organosilicon compounds have been extensively utilized both in industry and academia. Studies on the syntheses of diverse organosilanes is highly appealing. Through-space metal/hydrogen shifts allow functionalization of C?H bonds at a remote site, which are otherwise difficult to achieve. However, until now, an aryl to alkyl 1,5-palladium migration process seems to have not been presented. Reported herein is the remote olefination, arylation, and borylation of a methyl group on silicon to access diverse vinyl-, benzyl-, and borylsilanes, constituting a unique C(sp3)?H transformation based on a 1,5-palladium migration process.