ALLYLTRIMETHYLSILANE

CAS: 762-72-1

Ref. 3H-SIA0555.0

Product Information

• Name: ALLYLTRIMETHYLSILANE
• Synonyms: 3-(Trimethylsilyl)-1-propene, 3-(Trimethylsilyl)propene, Aliltrimetilsilano, Allyl(trimethyl)silane, Allyltrimethylisilane, Allyltrimethylsilan, Allytrimethylsilane, Sia 0555.0, Silane, allyltrimethyl-, Silane, trimethyl-2-propen-1-yl-, Silane, trimethyl-2-propenyl-, Trimethyl(2-propenyl)silane, Trimethyl(Prop-2-En-1-Yl)Silane, Trimethyl-2-propen-1-ylsilane, Trimethyl-prop-2-enylsilane, Trimethylallylsilane, Trimethylsilane, Allyl-, Allyltrimethylsilane

Description

Trimethylsilyl Blocking Agent
Used as a protecting group for reactive hydrogens in alcohols, amines, thiols, and carboxylic acids. Organosilanes are hydrogen-like, can be introduced in high yield, and can be removed under selective conditions. They are stable over a wide range of reaction conditions and can be removed in the presence of other functional groups, including other protecting groups. The tolerance of silylated alcohols to chemical transformations summary is presented in Table 1 of the Silicon-Based Blocking Agents brochure.
Alkenylsilane Cross-Coupling Agent
The cross-coupling reaction is a highly useful methodology for the formation of carbon-carbon bonds. It involves two reagents, with one typically being a suitable organometallic reagent - the nucleophile - and the other a suitable organic substrate, normally an unsaturated halide, tosylate or similar - the electrophile.
Allytrimethylsilane; Propenyltrimethylsilane; 3-Trimethylsilylpropene
Neutral propylene by-productAcid-catalyzed silylationsUsed for acids and thiolsEmployed in the synthesis of N-trimethylsilylpyridinium triflate an active trimethylsilylating agentNafion SAC-13 has been shown to be a recyclable catalyst for the trimethylsilylation of primary, secondary, and tertiary alcohols in excellent yields and short reaction timesReacts with vinyl bromides to give 1,4-dienes and Versatile synthon- transfers allyl group, highly nucleophilic double bondUndergoes polymerization with zirconocene complexesProvides functional termination of living carbocationic polymerized polyisobutylenesAllylates dioxolanesProvides alternative for the formation of trans-allyl-2,3-O-isopropylidene-protected pyrrolidinesCarries out deoxygenative allylation of benzylic alcoholsAllylates imines under fluoride catalysisReacts with allyl bromides to give 1,5-dienesDiallylates ketones via their ketalsForms benzylic homoallylic alcohols in a 3-component reaction with aldehydesAllylates lithium alkoxides w/ loss of the lithium oxideSummary of selective deprotection conditions is provided in Table 7 through Table 20 of the Silicon-Based Blocking Agents brochureExtensive review of silicon based cross-coupling agents: Denmark, S. E. et al. "Organic Reactions, Volume 75" Denmark, S. E. ed., John Wiley and Sons, 233, 2011

• Brand: Gelest

Chemical properties

• Molecular weight: 114.26
• Formula: C₆H₁₄Si
• Purity: 97%
• Color/Form: Straw Liquid