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698180 Sigma-Aldrich

Tris(trimethylsilyl)silyl vinyl ether

Synonym: Tris(trimethylsilyl)silyloxyethylene, Vinyloxytris(trimethylsilyl)silane

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Properties

Related Categories Building Blocks, Chemical Synthesis, Enol Ethers, Organic Building Blocks, Organometallic Reagents,
mp   51-61 °C
storage temp.   2-8°C
SMILES string   C[Si](C)(C)[Si](OC=C)([Si](C)(C)C)[Si](C)(C)C
InChI   1S/C11H30OSi4/c1-11-12-16(13(2,3)4,14(5,6)7)15(8,9)10/h11H,1H2,2-10H3
InChI key   WPZQENSANSNYSI-UHFFFAOYSA-N

Description

Application

Super Silyl Protecting Groups

Used for:
• Diastereoselective [2+2] cyclizations
• Cross-Aldol cascade reaction
• Diastereoselective sequential reactions for generating polyols
• Accessing distinct diastereomers and 4-component reactions
• Supersilyl-directed aldol reactions

• Strong electron-donating effect of the supersilyl group operates only in the α-position and not in the β-position

Safety & Documentation

Safety Information

Symbol 
Signal word 
Warning
Hazard statements 
Precautionary statements 
RIDADR 
UN1325 - class 4.1 - PG 3 - Flammable solids, organic, n.o.s., HI: all
WGK Germany 
3
Flash Point(F) 
170.6 °F
Flash Point(C) 
77 °C

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

Super Silyl Protecting Groups

Tris(trimethylsilyl)silane (360716) won the Fluka Reagent of the Year award in 1990 for its use as an alternative to tributylstannane (Bu3SnH) in radical reactions. Currently, the tris(trimethylsilyl...
Mark Redlich
Chemfiles Volume 9 Article 3

Yamamoto Group - Professor Product Portal

From our library of Articles, Sigma-Aldrich presents Yamamoto Group - Professor Product Portal
Keywords: Amidations, Asymmetric synthesis, Catalysis, Diels-Alder reaction, Epoxidations, Esterifications, Ligands, Oxidations

Related Content

Super Silyl Protecting Groups – Unique Reactivity in C–C Bond Forming Reactions

Tris(trimethylsilyl)silane, 360716 (Figure 1) is commonly used as an alternative to tributylstannane (Bu3SnH) in radical reactions. Tris(trimethylsilyl)silane has been used in hydrosilylations,1 radi...
Keywords: Addition reactions, Aldol reaction, Cyclizations, Deprotonations, Grignard Reaction, Hydrosilylations, Racemizations, Reductions, transformation

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