1009-43-4

Basic information

• Product Name: P-TRIMETHYLSILYL STYRENE
• Synonyms: P-TRIMETHYLSILYL STYRENE;TRIMETHYL-(4-VINYLPHENYL) SILANE;4-Trimethylsilylstyrene;Trimethyl(p-vinylphenyl)silane;(4-ethenylphenyl)triMethyl
• CAS NO: 1009-43-4
• Molecular Formula: C₁₁H₁₆Si
• Molecular Weight: 176.33
• Mol File: 1009-43-4.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 226℃
• Flash Point: 76℃
• Appearance: /
• Density: 0.86
• Refractive Index: 1.525
• CAS DataBase Reference: P-TRIMETHYLSILYL STYRENE(CAS DataBase Reference)
• NIST Chemistry Reference: P-TRIMETHYLSILYL STYRENE(1009-43-4)
• EPA Substance Registry System: P-TRIMETHYLSILYL STYRENE(1009-43-4)

Safety Data

• Hazardous Substances Data: 1009-43-4(Hazardous Substances Data)

Upstream product

• 18192-43-3 [4-(1-ethoxy-2-bromo-ethyl)-phenyl]-trimethyl-silane 
• 75-77-4 chloro-trimethyl-silane 
• 2039-82-9 1-bromo-4-ethenyl-benzene 
• 18042-44-9 4-trimethylsilylpropiophenone 
• 17865-11-1 (4-(trimethylsilyl)phenyl)boronic acid 
• 108-05-4 vinyl acetate 
• 6999-03-7 1-bromo-4-(trimethylsilyl)benzene 
• 1073-67-2 4-vinylbenzyl chloride 
• 2199-32-8 4-trimethylsilylbenzaldehyde 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 109-72-8 n-butyllithium 
• 17878-43-2 [4-(trimethylsilyl)phenyl]magnesium bromide 
• 1009-48-9 (ph-4-vi)SiCl₃ 
• 75-16-1 methylmagnesium bromide 

Downstream Products

• 17983-66-3 trimethyl-(4-oxiranyl-phenyl)-silane 
• 1082577-52-3 CH₂CHC₆H₄BBrC₄H₂S₂C₄H₂C₆H₁₃ 
• 3908-02-9 (E)-3-(4-(trimethylsilyl)phenyl)acrylic acid 
• 100-42-5 styrene 
• 1450728-59-2 2-(1-(4-(trimethylsilyl)phenyl)ethyl)-1-naphthaldehyde 

Relevant articles and documents

Design, Synthesis, and Implementation of Sodium Silylsilanolates as Silyl Transfer Reagents

There is an increasing demand for facile delivery of silyl groups onto organic bioactive molecules. One of the common methods of silylation via a transition-metal-catalyzed coupling reaction employs hydrosilane, disilane, and silylborane as major silicon sources. However, the labile nature of the reagents or harsh reaction conditions sometimes render them inadequate for the purpose. Thus, a more versatile alternative source of silyl groups has been desired. We hereby report a design, synthesis, and implementation of storable sodium silylsilanolates that can be used for the silylation of aryl halides and pseudohalides in the presence of a palladium catalyst. The developed method allows a late-stage functionalization of polyfunctionalized compounds with a variety of silyl groups. Mechanistic studies indicate that (1) a nucleophilic silanolate attacks a palladium center to afford a silylsilanolate-coordinated arylpalladium intermediate and (2) a polymeric cluster of silanolate species assists in the intramolecular migration of silyl groups, which would promote an efficient transmetalation.

Functionalized styrene synthesis via palladium-catalyzed C[sbnd]C cleavage of aryl ketones

We report herein the synthesis of functionalized styrenes via palladium-catalyzed Suzuki–Miyaura cross-coupling reaction between aryl ketone derivatives and potassium vinyltrifluoroborate. The employment of pyridine-oxazoline ligand was the key to the cleavage of unstrained C[sbnd]C bond. A variety of functional groups and biologically important moleculars were well tolerated. The orthogonal Suzuki–Miyaura coupling demonstrated the synthetic practicability.

Olefination via Cu-Mediated Dehydroacylation of Unstrained Ketones

The dehydroacylation of ketones to olefins is realized under mild conditions, which exhibits a unique reaction pathway involving aromatization-driven C-C cleavage to remove the acyl moiety, followed by Cu-mediated oxidative elimination to form an alkene between the α and β carbons. The newly adopted N′-methylpicolinohydrazonamide (MPHA) reagent is key to enable efficient cleavage of ketone C-C bonds at room temperature. Diverse alkyl- and aryl-substituted olefins, dienes, and special alkenes are generated with broad functional group tolerance. Strategic applications of this method are also demonstrated.