40595-34-4

Basic information

• Product Name: trimethyl[(2E)-3-phenylprop-2-en-1-yl]silane
• Synonyms: cinnamyltrimethylsilane; Silane, trimethyl(3-phenyl-2-propenyl)-
• CAS NO: 40595-34-4
• Molecular Formula: C₁₂H₁₈Si
• Molecular Weight: 190.3568
• Mol File: 40595-34-4.mol
• Article Data: 57

Chemical Properties

• Boiling Point: 243.4°C at 760 mmHg
• Flash Point: 88.2°C
• Density: 0.882g/cm³
• Vapor Pressure: 0.0503mmHg at 25°C
• Refractive Index: 1.512
• CAS DataBase Reference: trimethyl[(2E)-3-phenylprop-2-en-1-yl]silane(CAS DataBase Reference)
• NIST Chemistry Reference: trimethyl[(2E)-3-phenylprop-2-en-1-yl]silane(40595-34-4)
• EPA Substance Registry System: trimethyl[(2E)-3-phenylprop-2-en-1-yl]silane(40595-34-4)

Safety Data

• Hazardous Substances Data: 40595-34-4(Hazardous Substances Data)

Upstream product

• 63922-84-9 2-(trimethylsilyl)ethyltriphenylphosphonium iodide 
• 100-52-7 benzaldehyde 
• 75-77-4 chloro-trimethyl-silane 
• 7217-71-2 1-phenyl-2-propenyl acetate 
• 1450-14-2 1,1,1,2,2,2-hexamethyldisilane 
• 21040-45-9 Cinnamyl acetate 
• 40595-35-5 (Z)-1-phenyl-3-(trimethylsilyl)-1-propene 
• 156-60-5 trans-1,2-dichloroethylene 
• 2344-80-1 Chloromethyltrimethylsilane 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 87802-71-9 (E)-methyl cinnamyl carbonate 
• 85669-63-2 (E)-cinnamyl diethyl phosphate 
• 101306-31-4 benzyl cinnamyl ether 
• 17763-67-6 Phenyl triflate 

Downstream Products

• 96746-40-6 4-phenyl-5-hexen-1-ol 
• 1825-61-2 Trimethylmethoxysilane 
• 22665-13-0 1-phenylallyl methyl ether 
• 24808-73-9 (E)-(3-methoxyprop-1-en-1-yl)benzene 
• 90929-16-1 (2E)-3-phenylprop-2-en-1-yl nitrate 
• 135121-13-0 (3S,4R)-3-Phenyl-4-trimethylsilanylmethyl-azetidin-2-one 
• 74120-63-1 (E)-1,4-diphenyl-1,5-hexadiene 
• 76524-55-5 (E)-(5-methylhexa-1,5-dienyl)benzene 
• 73222-66-9 (5-methylhexa-1,5-dien-3-yl)benzene 
• 68060-18-4 (4-methylhexa-1,5-dien-3-yl)benzene 
• 76524-56-6 4-methyl-1-phenyl-1,5-hexadiene 
• 105140-54-3 (E)-3,3,6,6-Tetramethyl-7-phenyl-nona-4,8-dienal 
• 105140-45-2 ((E)-2,2,5,5-Tetramethyl-1-vinyl-hepta-3,6-dienyl)-benzene 
• 21087-29-6 trans-3-phenylprop-2-enyl chloride 

Relevant articles and documents

Electrophilic difluoro(phenylthio)methylation: Generation, stability, and reactivity of α-fluorocarbocations

Electrophilic difluoro(phenylthio)methylation of allylsilanes has been achieved using bromodifluoro(phenylthio)methane (PhSCF2Br) and silver hexafluoroantimonate (AgSbF6). The structural assignment and observation of α-fluorocarbocation were substantiated by NMR and theoretical calculations. Detailed mechanistic and electronic studies have provided a fundamental understanding of the reactivity and stability of the difluoro(phenylthio)methylium cation (PhSCF2+).

Diastereoselective Addition of Prochiral Nucleophilic Alkenes to α-Chiral N-Sulfonyl Imines

The Lewis-acid-promoted addition of prochiral E- and Z-allyl nucleophiles to chiral α-alkoxy N-tosyl imines is described. Alkene geometry is selectively transferred to the newly formed carbon-carbon bond, resulting in stereochemical control of C1, C2, and C3 of the resulting 2-alkoxy-3-N-tosyl-4-alkyl-5-hexene products. A computational analysis to elucidate the high selectivity is also presented. This methodology was employed in the synthesis of two naturally occurring isomers of clausenamide.

Oxoammonium-Mediated Allylsilane–Ether Coupling Reaction

A new C(sp3)?H functionalization reaction consisting of the oxidative α-allylation of allyl- and benzyl- methyl ethers has been developed. The C?C coupling could be carried out under mild conditions thanks to the use of cheap and green oxoammonium salts. The scope of the reaction was studied over 27 examples, considering the nature of the substituents on the two coupling partners.

Visible Light-Induced Room-Temperature Heck Reaction of Functionalized Alkyl Halides with Vinyl Arenes/Heteroarenes

The first visible light-induced Pd-catalyzed Heck reaction of α-heteroatom substituted alkyl iodides and -bromides with vinyl arenes/heteroarenes has been developed. This transformation efficiently proceeds at room temperature and enables synthesis of valuable functionalized allylic systems, such as allylic silanes, boronates, germanes, stannanes, pivalates, phosphonates, phthalimides, and tosylates from the corresponding α-substituted methyl iodides. Notably, synthesis of the latter substrates failed under existing thermally induced Pd-catalyzed conditions, which highlights the importance of visible light for this transformation.