53282-55-6

Basic information

• Product Name: (cyclohexylidenemethoxy)(trimethyl)silane
• Synonyms: cyclohexane, [[(trimethylsilyl)oxy]methylene]-; Cyclohexylidenemethyl trimethylsilyl ether
• CAS NO: 53282-55-6
• Molecular Formula: C₁₀H₂₀OSi
• Molecular Weight: 184.3507
• Mol File: 53282-55-6.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 195.8°C at 760 mmHg
• Flash Point: 61.7°C
• Density: 0.927g/cm³
• Vapor Pressure: 0.577mmHg at 25°C
• Refractive Index: 1.498
• CAS DataBase Reference: (cyclohexylidenemethoxy)(trimethyl)silane(CAS DataBase Reference)
• NIST Chemistry Reference: (cyclohexylidenemethoxy)(trimethyl)silane(53282-55-6)
• EPA Substance Registry System: (cyclohexylidenemethoxy)(trimethyl)silane(53282-55-6)

Safety Data

• Hazardous Substances Data: 53282-55-6(Hazardous Substances Data)

Usage

General Description

The chemical compound (cyclohexylidenemethoxy)(trimethyl)silane, often referred to as CHMOTMS, is an organosilicon compound with the molecular formula C10H24OSi. It is commonly used as a reagent in organic synthesis, specifically in the synthesis of various silicon-based materials and compounds. It possesses a cyclohexylidene functional group and three trimethylsilyl groups attached to a silicon atom, making it a versatile building block in the production of silicon-containing polymers, resins, and coatings. CHMOTMS is also known for its ability to act as a hydrogen acceptor in catalytic hydrogenation reactions, and it is frequently utilized in the modification of surfaces and interfaces in various chemical processes and applications.

Upstream product

• 31469-15-5 1-methoxy-2-methyl-1-trimethylsiloxy-1-propene 
• 2043-61-0 cyclohexanecarbaldehyde 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 
• 27607-77-8 trimethylsilyl trifluoromethanesulfonate 
• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 75-77-4 chloro-trimethyl-silane 
• 100-49-2 cyclohexylmethyl alcohol 
• 993-07-7 trimethylsilan 
• 201230-82-2 carbon monoxide 
• 622-45-7 cyclohexyl acetate 
• 110-83-8 cyclohexene 

Downstream Products

• 53282-32-9 cyclohexylidenemethyl trifluoromethanesulfonate 
• 95541-06-3 2,4-Dicyclohexyl-5-[2,2,3,3,3-pentafluoro-prop-(E)-ylidene]-[1,3]dioxolane 
• 95540-94-6 1-Cyclohexyl-4,4,5,5,5-pentafluoro-pent-2-yn-1-ol 
• 95540-90-2 1-Cyclohexyl-4,4,4-trifluoro-2-butyn-1-ol 
• 95541-03-0 2,4-Dicyclohexyl-5-[2,2,2-trifluoro-eth-(E)-ylidene]-[1,3]dioxolane 
• 127827-62-7 1-Formyl-1-(3-butenyl)cyclohexane 
• 65946-62-5 Phenylseleno-1 cyclohexylcarboxaldehyde 
• 181060-03-7 1-methylsulfanyl-cyclohexanecarboxaldehyde 
• 181060-04-8 1-ethylsulfanyl-cyclohexanecarboxaldehyde 
• 6140-64-3 1-methylcyclohexanecarbaldehyde 
• 57768-35-1 1-(phenylthio)-1-cyclohexanecarboxaldehyde 
• 88386-36-1 1-(1-Methyl-3-oxobutyl)cyclohexancarboxaldehyd 
• 56037-77-5 1-(acetyloxy)cyclohexanecarboxaldehyde 
• 1192-88-7 1-cyclohexene-1-carboxaldehyde 

Relevant articles and documents

Chemiluminescence-promoted oxidation of alkyl enol ethers by NHPI under mild conditions and in the dark

The hydroperoxidation of alkyl enol ethers using N-hydroxyphthalimide and molecular oxygen occurred in the absence of catalyst, initiator, or light. The reaction proceeds through a radical mechanism that is initiated by N-hydroxyphthalimide-promoted autoxidation of the enol ether substrate. The resulting dioxetane products decompose in a chemiluminescent reaction that allows for photochemical activation of N-hydroxyphthalimide in the absence of other light sources.

One-pot enol silane formation-Mukaiyama aldol reactions: Crossed aldehyde-aldehyde coupling, thioester substrates, and reactions in ester solvents

Trimethylsilyl trifluoromethanesulfonate (TMSOTf) and a trialkylamine base promote both in situ enol silane/silyl ketene acetal formation and Mukaiyama aldol addition reactions between a variety of reaction partners in a single reaction flask. Isolation of the required enol silane or silyl ketene acetal is not necessary. For example, crossed aldol reactions between α-disubstituted aldehydes and non-enolizable aldehydes yield β-hydroxy aldehydes in good yield. In a related reaction, the common laboratory solvent ethyl acetate functions as both an enolate precursor and a green reaction solvent. When thioesters are employed as enolate precursors, high yields for additions to non-enolizable aldehydes are routinely observed.

Preparation of silyl enol ethers using (bistrimethylsilyl)acetamide in ionic liquids

(matrix presented) Ionic liquids have been used for the preparation of silyl enol ethers from aldehydes and ketones with (bistrimethylsilyl)acetamide (BSA) in good yields.