28129-04-6

Basic information

• Product Name: Silane, trimethyl(3-phenyl-1-butynyl)-
• CAS NO: 28129-04-6
• Molecular Formula: C13H18Si
• Molecular Weight: 202.371
• Mol File: 28129-04-6.mol

Chemical Properties

• CAS DataBase Reference: Silane, trimethyl(3-phenyl-1-butynyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, trimethyl(3-phenyl-1-butynyl)-(28129-04-6)
• EPA Substance Registry System: Silane, trimethyl(3-phenyl-1-butynyl)-(28129-04-6)

Safety Data

• Hazardous Substances Data: 28129-04-6(Hazardous Substances Data)

Upstream product

• 100-41-4 ethylbenzene 
• 1066-54-2 trimethylsilylacetylene 
• 1253840-86-6 C₉H₁₉NSi 
• 100-58-3 phenylmagnesium bromide 
• 75-77-4 chloro-trimethyl-silane 
• 77295-70-6 (4,4-dibromobut-3-en-2-yl)benzene 
• 34713-70-7 2-Phenylpropanal 
• 98-86-2 acetophenone 
• 4544-28-9 3-phenyl-1-butyne 
• 673-32-5 1-Phenylprop-1-yne 
• 74-83-9 methyl bromide 

Downstream Products

• 1159582-94-1 C₂₂H₂₆Si 
• 1159582-95-2 C₂₂H₂₅BrSi 
• 1416452-45-3 1-(1-ethyl-1H-indol-2-yl)-4-phenyl-3λ⁵-penta-2,3-dien-1-ol 
• 78341-15-8 [η4-1,2,3-tris(trimethylsilyl)-4-(1-phenylethyl)cyclobutadiene](η5-cyclopentadienyl)cobalt 
• 779348-91-3 (3,5-dimethyl-3-phenyl-hex-5-en-1-ynyloxy)-triisopropyl-silane 

Relevant articles and documents

Three-coordinate copper(II) alkynyl complex in C-C bond formation: The sesquicentennial of the glaser coupling

Copper(II) alkynyl species are proposed as key intermediates in numerous Cu-catalyzed C-C coupling reactions. Supported by a β-diketiminate ligand, the three-coordinate copper(II) alkynyl [CuII]-C≡CAr (Ar = 2,6-Cl2C6H3) forms upon reaction of the alkyne H-C≡CAr with the copper(II) tertbutoxide complex [CuII]-OtBu. In solution, this [CuII]-C≡CAr species cleanly transforms to the Glaser coupling product ArC≡C-C≡CAr and [CuI](solvent). Addition of nucleophiles R′C≡C-Li (R′ = aryl, silyl) and Ph-Li to [CuII]-C≡CAr affords the corresponding Csp-Csp and Csp-Csp2 coupled products RC≡C-C≡CAr and Ph-C≡CAr with concomitant generation of [CuI](solvent) and {[CuI]-C≡CAr}-, respectively. Supported by density functional theory (DFT) calculations, redox disproportionation forms [CuIII](C≡CAr)(R) species that reductively eliminate R-C≡CAr products. [CuII]-C≡CAr also captures the trityl radical Ph3C· to give Ph3C-C≡CAr. Radical capture represents the key Csp-Csp3 bond-forming step in the copper-catalyzed C-H functionalization of benzylic substrates R-H with alkynes H-C≡CR′ (R′ = (hetero)aryl, silyl) that provide Csp-Csp3 coupled products R-C≡CR via radical relay with tBuOOtBu as oxidant.

Regio- and Stereospecific Copper-Catalyzed Substitution Reaction of Propargylic Ammonium Salts with Aryl Grignard Reagents

We have developed a copper-catalyzed substitution reaction of propargylic ammonium salts with aryl Grignard reagents. The reaction is stereospecific and α-regioselective and proceeds with exceptional functional group tolerance. Conveniently, a stable, inexpensive, and commercially available copper salt is used and no added ligand is required.

Direct Synthesis of α-Allenols from TMS-Protected Alkynes and Aldehydes Mediated by Tetrabutylammonium Fluoride

A unique chemoselective synthesis of α-allenic alcohols is presented. Tetrabutylammonium fluoride (TBAF) mediated this transformation under mild reaction conditions. A range of functional groups is well-tolerated in this reaction, while affording adducts

Stereo- and regiocontrol in ene-dimerisation and trimerisation of 1-trimethylsilyl-3-phenylcyclopropene

1-Trimethylsilyl-3-phenylcyclopropene and its 2D-analog undergo a highly stereocontrolled ene-reaction to give a single dimer. Further reaction leads to one or more trimers derived through two ene-reactions. The dimer formed easily undergoes cycloaddition