853955-58-5

Basic information

• Product Name: Silane, dimethyl[2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]-
• CAS NO: 853955-58-5
• Molecular Formula: C14H22O2Si
• Molecular Weight: 250.413
• Mol File: 853955-58-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: Silane, dimethyl[2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, dimethyl[2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]-(853955-58-5)
• EPA Substance Registry System: Silane, dimethyl[2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]phenyl]-(853955-58-5)

Safety Data

• Hazardous Substances Data: 853955-58-5(Hazardous Substances Data)

Upstream product

• 110-87-2 3,4-dihydro-2H-pyran 
• 18982-54-2 o-bromobenzyl alcohol 
• 17100-66-2 2-(tetrahydropyranyloxy)methylbromobenzene 
• 1066-35-9 dimethylmonochlorosilane 

Downstream Products

• 944064-51-1 [2-(hydroxymethyl)phenyl]dimethyl(4-methoxyphenyl)silane 
• 1217863-25-6 [2-(hydroxymethyl)phenyl]dimethyl(4-chlorophenyl)silane 
• 1383440-74-1 C₂₂H₂₉NO₂Si 
• 1383440-87-6 C₂₇H₃₇NO₃Si 
• 1383440-56-9 C₂₂H₃₄O₄Si 
• 1383440-57-0 C₁₇H₂₆O₃Si 
• 1383440-72-9 C₁₈H₂₉NO₃Si 
• 1383440-86-5 C₂₃H₃₇NO₄Si 
• 1383440-71-8 C₂₀H₃₃NO₂Si 
• 1383440-85-4 C₂₅H₄₁NO₃Si 
• 137129-03-4 N,N-dibenzyl-2,4,6-trimethylaniline 

Relevant articles and documents

Straightforward synthesis of HOMSi reagents via sp2 C-H silylation

Straightforward C-H silylation of heteroarenes and alkenes was found to provide efficient access to organo-HOMSi reagents as stable silicon reagents for cross-coupling. Various heteroarenes and terminal alkenes were silylated to show the versatility of the reaction. This method was applied in double silylation reactions to give bisHOMSi reagents. The silylation products could be used in the cross-coupling reaction with haloarenes easily.

Improved Hiyama cross-coupling reactions using HOMSi

Various parameters in the Hiyama cross-coupling reaction of HOMSi reagents with ethyl bromobenzoate were studied. These included solvent, ligand, palladium source, and added water. DMF and THF were found to be excellent solvents. Palladium chloride was found to be the best palladium source and no added water was required. The use of tri-o-tolylphosphine as the ligand proved to be particularly effective.

Synthesis and cross-coupling reaction of alkenyl[(2-hydroxymethyl)phenyl]dimethylsilanes

Highly stable alkenyl[2-(hydroxymethyl)phenyl]dimethylsilanes are prepared by stereo- and regioselective hydrosilylation of alkynes catalyzed either by a platinum or ruthenium catalyst using protected [2-(hydroxymethyl)phenyl]dimethylsilanes. Cyclic silyl ether, 1,1-dimethyl-2-oxa-1-silaindan, also serves as a starting material for the alkenylsilanes by the ring-opening reaction with alkenyl Grignard reagents. The resulting alkenylsilanes undergo cross-coupling reaction with various aryl and alkenyl iodides under reaction conditions employing K2CO3 as a base at 35-50 °C in highly regio- and stereospecific manners. The reaction tolerates a diverse range of functional groups including silyl protections. The silicon residue is readily recovered and reused on a gram-scale synthesis. Intramolecular coordination of a proximal hydroxyl group is considered to efficiently form pentacoordinate silicates having a transferable group possibly at an axial position and, thus, responsible for the cross-coupling reaction under conditions significantly milder than those reported for the silicon-based reactions.