65946-59-0

Basic information

• Product Name: 1,1-BIS(TRIMETHYLSILYLOXY)-2-TRIMETHYLSILYLETHENE
• Synonyms: (TRIMETHYLSILYL)KETENE BIS(TRIMETHYL-SIL YL) ACETAL;1,1-BIS(TRIMETHYLSILYLOXY)-2-TRIMETHYLSILYLETHENE
• CAS NO: 65946-59-0
• Molecular Formula: C₁₁H₂₈O₂Si₃
• Molecular Weight: 276.6
• Mol File: 65946-59-0.mol

Chemical Properties

• Boiling Point: 86 °C10 mm Hg(lit.)
• Flash Point: 106 °F
• Appearance: /
• Density: 0.848 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.139mmHg at 25°C
• Refractive Index: n20/D 1.428(lit.)
• Storage Temp.: 0-6°C
• CAS DataBase Reference: 1,1-BIS(TRIMETHYLSILYLOXY)-2-TRIMETHYLSILYLETHENE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,1-BIS(TRIMETHYLSILYLOXY)-2-TRIMETHYLSILYLETHENE(65946-59-0)
• EPA Substance Registry System: 1,1-BIS(TRIMETHYLSILYLOXY)-2-TRIMETHYLSILYLETHENE(65946-59-0)

Safety Data

• Statements: 10
• Safety Statements: 16
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• Hazardous Substances Data: 65946-59-0(Hazardous Substances Data)

Usage

Usage

Building block in organic synthesis

Specific use

Production of silicone polymers and resins

Reactivity

Reactive intermediate

Chemical reactions

Can undergo addition and substitution reactions

Protective group

Used to block the reactivity of certain functional groups in organic chemistry

Applications

Key ingredient in the production of specialty coatings, adhesives, and sealants

Role

Crucial in the synthesis and production of various silicone-based materials

Industries

Chemical and materials industries

InChI:InChI=1/C11H28O2Si3/c1-14(2,3)10-11(12-15(4,5)6)13-16(7,8)9/h10H,1-9H3

Upstream product

• 2754-27-0 trimethylsilyl acetate 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 75-77-4 chloro-trimethyl-silane 
• 24082-11-9 α-trimethylsilyl trimethylsilylacetic ester 

Downstream Products

• 19866-51-4 (Z)-3-methyl-2-pentenoic acid 
• 19866-50-3 (E)-3-methylpent-2-enoic acid 
• 704-79-0 (Z)-3-phenylbut-2-enoic acid 
• 704-80-3 (E)-3-phenyl-2-butenoic acid 
• 606-84-8 3,3-diphenylacrylic acid 
• 140-10-3 cis-cinnamic acid 
• 140-10-3 (E)-3-phenylacrylic acid 

Relevant articles and documents

KOH-promoted reaction of C,O,O-tris(trimethylsilyl) ketene acetal with aldehydes: Practical and easy access to (E)-α,β-ethylenic carboxylic acids

The use of a catalytic amount of KOH has been found to be very efficient in promoting reaction of silylketene acetal 1 with aldehydes 2 to afford the corresponding (E)-α,β-ethylenic carboxylic acids 3 under very mild conditions.

Two-carbon homologation of aldehydes via silyl ketene acetals: A new stereoselective approach to (E)-alkenoic acids

Aldehydes are converted into (E)-α,β-unsaturated carboxylic acids using C,O,O-tris(trimethylsilyl)ketene acetal 1. This organosilicon reagent is easily generated from trimethylsilyl acetate, LDA, and chlorotrimethylsilane. The effectiveness of the reaction has been explored for a large variety of aldehydes with Lewis acids and fluorides as catalysts.

STEREOSELECTIVE SYNTHESIS OF (E)-α,β-UNSATURATED ACIDS FROM C,O,O-TRI(TRIMETHYLSILYL) KETENE ACETAL AND ALDEHYDS

Aldehydes are converted into (E)-α,β-unsatured carboxylic acids by means of C,O,O-tri(trimethylsilyl) ketene acetal and a catalytic a mount of ZnBr2.

Reactions of Trialkylsilyl Trifluoromethanesulfonates, II. - Synthesis of O-Alkyl-O-(trialkylsilyl)ketene Acetals and 2-(Trialkylsilyl)carboxylates

Alkyl carboxylates 2 are silylated by trialkylsilyl triflates 1 in the presence of triethylamine (3) to yield ketene acetals 4.In reactions of the esters 6 mixtures of ketene acetals 7 and at the α-carbon silylated esters 8 are obtained.Ethanoic acid esters and lactones are doubly silylated to give the products 11, 12, and 15, respectively.Under suitable conditions silylation of the esters 10 gives rise to the 2-trimethylsilylethanoic acid esters 13.The thermodynamically more stable products are obtained.Product distributions depend on the structure of the esters and the silylating agents 1.