66270-74-4

Basic information

• Product Name: Silane, (2-cyclohexylethenyl)trimethyl-, (E)-
• CAS NO: 66270-74-4
• Molecular Formula: C11H22Si
• Molecular Weight: 182.381
• Mol File: 66270-74-4.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: Silane, (2-cyclohexylethenyl)trimethyl-, (E)-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, (2-cyclohexylethenyl)trimethyl-, (E)-(66270-74-4)
• EPA Substance Registry System: Silane, (2-cyclohexylethenyl)trimethyl-, (E)-(66270-74-4)

Safety Data

• Hazardous Substances Data: 66270-74-4(Hazardous Substances Data)

Upstream product

• 67-56-1 methanol 
• 76346-96-8 C₁₁H₂₁LiSi 
• 66270-60-8 (cyclohexylethynyl)trimethylsilane 
• 2612-42-2 (dibromomethyl)trimethylsilane 
• 2043-61-0 cyclohexanecarbaldehyde 
• 110-82-7 cyclohexane 
• 1066-54-2 trimethylsilylacetylene 
• 1568-65-6 bis(cyclohexanyl)borane 
• 931-51-1 cyclohexylmagnesiumchloride 
• 29955-07-5 trimethyl(diiodomethyl)silane 
• 336193-41-0 2-chloro-1-cyclohexyl-2-(trimethylsilyl)ethyl acetate 
• 336193-49-8 2-chloro-1-cyclohexyl-2-trimethylsilanyl-ethanol 

Downstream Products

• 67404-71-1 (E)-(2-chloroethenyl)cyclohexane 
• 42599-23-5 ((E)-2-iodovinyl)cyclohexane 

Relevant articles and documents

Transformation of aldehydes into (E)-1-alkenylsilanes and (E)-1-alkenylboronic esters with a catalytic amount of a chromium salt

(Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me 3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, and a catalytic amount of CrCl 3[thf]3 in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR) 2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.

One-pot transformation of RCHO to (E)-RCH=CHSiMe3 using CHI3, Mn, Me3SiCl, and a catalytic amount of CrCl2

Iodoform is reduced with manganese in the presence of Me3SiCl to give Me3SiCHI2 (1). A one-pot transformation of aldehydes to (E)-1- alkenyltrimethylsilanes is then performed with iodoform, manganese, Me2SiCl, and a catalytic amount of chromium(II) chloride in THF via in situ formation of 1.

The Hydroboration of (Trimethylsilyl)ethyne with Dialkylboranes and its Application to the Synthesis of (E)-1-(Trimethylsilyl)alk-1-enes and 2-(Trimethylsilyl)alk-1-enes

The reaction of (trimethylsilyl)ethyne 1 with a stoicheiometric amount of dialkylborane 2 proceeds to the monohydroboration stage, giving a mixture of regioisomers, (E)-dialkylborane 3 and dialkylborane 4.In the hydroboration with bulky dialkylboranes, derived from internal alkenes, the former predominates.Successive treatment of the mixture with methyllithium and benzenesulphenyl chloride exclusively affords highly pure (E)-2-alkyl-1-(trimethylsily)ethene 6 whose alkyl group migrates from the boron atom, while in the hydroboration with less bulky dialkylboranes, derived from terminal alkenes, the latter predominates.Successive treatment of the mixture with aq.NaOH and iodine exclusively affords highly pure 2-(trimethylsilyl)alk-1-ene 7 whose alkyl group migrates from the boron atom.