31683-47-3

Basic information

• Product Name: trimethyl(3-phenylprop-1-ynyl)silane
• Synonyms: trimethyl(3-phenylprop-1-ynyl)silane;1-(Trimethylsilyl)-3-phenyl-1-propyne
• CAS NO: 31683-47-3
• Molecular Formula: C₁₂H₁₆Si
• Molecular Weight: 188.34094
• Mol File: 31683-47-3.mol
• Article Data: 29

Chemical Properties

• Appearance: /
• CAS DataBase Reference: trimethyl(3-phenylprop-1-ynyl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: trimethyl(3-phenylprop-1-ynyl)silane(31683-47-3)
• EPA Substance Registry System: trimethyl(3-phenylprop-1-ynyl)silane(31683-47-3)

Safety Data

• Hazardous Substances Data: 31683-47-3(Hazardous Substances Data)

Upstream product

• 75-77-4 chloro-trimethyl-silane 
• 10147-11-2 propargyl benzene 
• 100-39-0 benzyl bromide 
• 250643-77-7 tris(2-(trimethylsilyl)ethynyl)indium 
• 1066-54-2 trimethylsilylacetylene 
• 61210-52-4 (trimethylsilyl)ethynylmagnesium bromide 
• 38002-45-8 3-bromo-1-(trimethylsilyl)-1-propyne 
• 54655-07-1 lithium trimethylsilylacetylenide 
• 260783-80-0 N,N,N--trimethyl--1--phenylmethanaminium trifluoromethanesulfonate 
• 56849-88-8 N,N-dimethyl-3-(trimethylsilyl)prop-2-yn-1-amine 
• 100-58-3 phenylmagnesium bromide 
• 100-44-7 benzyl chloride 
• 762-72-1 allyl-trimethyl-silane 
• 166734-87-8 Pd(P(C₆H₅)3)2(CH₂CHCHSi(CH₃)3)⁽¹⁺⁾*B(C₆H₅)4^(1-)=[Pd(P(C₆H₅)3)2(CH₂CHCHSi(CH₃)3)]B(C₆H₅)4 

Downstream Products

• 31650-09-6 1,3-bis(trimethylsilyl)-3-phenyl-allene 
• 31650-08-5 1,3-bis(trimethylsilyl)-3-phenyl-1-propyne 
• 89828-25-1 (Z)-1-phenyl-3-trimethylsilyl-2-heptene 
• 73727-44-3 (Z)-trimethyl(3-phenylprop-1-en-1-yl)silane 
• 58040-61-2 (1,3-diphenylpropa-1,2-dien-1-yl)trimethylsilane 

Relevant articles and documents

Pd-catalyzed sp-sp3cross-coupling of benzyl bromides using lithium acetylides

Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C-C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp2, and sp3) with aromatic (pseudo) halides (sp2). Here we present an efficient method for the cross-coupling of benzyl bromides (sp3) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products.

Palladium-Catalyzed Coupling of Terminal Alkynes with Benzyl Ammonium Salts

A highly efficient palladium-catalyzed Sonogashira coupling of benzylic ammonium salts with terminal alkynes is developed. This strategy provides a facile access to a series of internal alkyne derivatives in moderate to excellent yields via C-N bond cleavage and C(sp3)-C(sp) bond formation. The broad substrate scope and high functional group tolerance make this reaction attractive for organic synthesis.

Propargylsilanes as Reagents for Synergistic Gold(I)-Catalyzed Propargylation of Carbonyl Compounds: Isolation and Characterization of σ-Gold(I) Allenyl Intermediates

Reported herein is the isolation and characterization, for the first time, of a σ-gold allenyl complex as an intermediate in gold catalysis. This intermediate was captured during the study of a novel gold(I)-catalyzed propargylation of carbonyl compounds with propargylsilanes. Notably, the gold-catalyzed propargylation reaction, which proceeds with aldehydes and ketones, can be driven to the formation of either homopropargyl silyl ethers or the in situ synthesis of corresponding 2-silyl-4,5-dihydrofurans.