95061-68-0

Usage

Uses

Used in Silicone Production:
(1-HYDROXYALLYL)TRIMETHYLSILANE is used as a crosslinking agent for the production of polymers and other silicone-based materials. Its ability to form crosslinks is crucial in creating stable silicone networks, which are essential for various applications in the polymer industry.
Used in Organic Synthesis:
(1-HYDROXYALLYL)TRIMETHYLSILANE is used as a building block in the synthesis of various organic compounds. Its unique structure allows it to be a valuable component in the creation of a wide range of organic molecules, contributing to the development of new chemical products and innovations.
Safety Considerations:
It is important to handle (1-HYDROXYALLYL)TRIMETHYLSILANE with care due to its flammable nature and potential harmful effects if inhaled or ingested. Proper safety measures should be taken during its use to ensure the well-being of individuals and the environment.

InChI:InChI=1/C6H14OSi/c1-5-6(7)8(2,3)4/h5-7H,1H2,2-4H3

Upstream product

• 18146-00-4 allyloxytrimethylsilane 
• 1826-67-1 vinyl magnesium bromide 
• 106881-72-5 2,2-Dimethyl-2-silapropanal 
• 75-77-4 chloro-trimethyl-silane 
• 107-18-6 allyl alcohol 

Downstream Products

• 18052-94-3 1-(trimethylsilyl)-1-(benzoyloxy)-2-propene 
• 250234-74-3 trimethyl-[1-(1-phenyl-allyloxy)-allyl]-silane 
• 911466-04-1 (E)-(1-(cinnamyloxy)allyl)trimethylsilane 
• 250234-79-8 (1-benzyloxy-allyl)-trimethyl-silane 
• 121386-64-9 α-(trimethylsilyl)-n-propyl alcohol 
• 193970-99-9 C₂₀H₁₃F₁₀N₃O₃SSi 

Relevant academic research and scientific papers

α-β Unsaturated Acylsilanes as Surrogates of Acrolein for Morita–Baylis–Hillman Reactions

α-β-unsaturated acylsilanes are excellent substrates for Morita–Baylis–Hillman (MBH) reactions, affording the expected adducts in good to excellent yields. In these derivatives, as well as the corresponding acetates, the acylsilanes can be smoothly transf

Switchable C-H Functionalization of N-Tosyl Acrylamides with Acryloylsilanes

A controllable Rh-catalyzed protocol to access alkylation and alkenylation-annulation of N-tosyl acrylamide with acryloyl silane is reported. In contrast to the directing group or catalyst-dependent divergent sp2 C-H alkylation/alkenylation, the intrinsic property of acryloylsilane allows the switchable reaction manifold, thereby affording either alkylation or annulation products with slight modification of the reaction conditions.

Stereoconvergent [1,2]- and [1,4]-wittig rearrangements of 2-silyl-6-aryl-5,6-dihydropyrans: A tale of steric Vs electronic regiocontrol of divergent pathways

The regiodivergent ring contraction of diastereomeric 2-silyl-5,6-dihydro-6-aryl-(2H)-pyrans via [1,2]- and [1,4]-Wittig rearrangements to the corresponding α-silylcyclopentenols or (α-cyclopropyl)acylsilanes favor the [1,4]-pathway by ortho and para directing groups in the aromatic appendage and/or by sterically demanding silyl groups. The [1,2]-pathway is dominant with meta directing or electron-poor aromatic moieties. Exclusive [1,2]-Wittig rearrangements are observed when olefin substituents proximal to the silyl are present. cis and trans diastereomers exhibit different reactivities, but converge to a single [1,2]- or [1,4]-Wittig product with high diastereoselectivity and yield.

Divergent Functionalization of Indoles with Acryloyl Silanes via Rhodium-Catalyzed C-H Activation

(Chemical Equation Presented) A protocol enabled by rhodium-catalyzed C-H functionalization of indoles with acryloyl silanes was developed, providing a convenient and highly effective method for the synthesis of functionalized acylsilane derivatives. By tuning the reaction condition, this C-H-activation-initiated reaction proceeds divergently with acryloyl silianes to selectively afford alkylation or alkenylation products via hydroarylation or oxidative cross-coupling, respectively. The mild reaction conditions employed in both cases enable the tolerance of a wide scope of functionalities as well as high reaction efficiency. Furthermore, polycyclic indole derivatives were easily accessed from 2-alkenylation products through a visible-light-induced reaction cascade.

Synthesis of acylsilanes via nickel-catalyzed reactions of α-hydroxyallylsilanes

The redox isomerization processes and tandem isomerization-aldolization reactions, mediated by nickel catalysts, offer new versatile entries to acylsilanes. For the second reaction, high diastereoselectivities, up to 98:2, have been obtained with bulky substituents on silicon.

Enzymatic kinetic resolution of α-hydroxysilanes

The enzymatic kinetic resolution of α-hydroxysilanes where the silicon bears a variety of substituents has been explored. Reactions were performed on various α-hydroxysilanes with several commercially available enzymes, solvents, acetylation reagents, and temperatures. The resulting optically active α-hydroxysilanes and their corresponding acetates were obtained in varying yields and ees.

Synthesis and fluoride-promoted Wittig rearrangements of α-alkoxysilanes

(matrix presented) Lewis acid-catalyzed reaction of allyl and benzyl trichloroacetimidates with α-silyl alcohols was found to be a general method for the synthesis of α-alkoxysilanes. Upon exposure to CsF, these α-alkoxysilanes could be made to undergo [2,3]-Wittig rearrangement with an efficiency similar to that realized by the analogous but inherently more toxic α-alkoxystannanes.

The Reaction of Polyhalides with Allylsilanes Catalyzed by Copper(I) Chloride

Allyltrimethylsilane reacted with polyhalogen compounds in the presence of copper species, such as copper(I) chloride, copper(II) chloride or metallic copper, to form polyhalo compounds containing an allyl group. Other allylsilane derivatives than allyltrimethylsilane were also subjected to a reaction with carbon tetrachloride. 3-Chloro- or 3-bromo-3-trimethylsilyl-1-propene gave 4,4,4-trichloro-1-trimethylsilyl-1-butene. Ethyl 1-trimethylsilylallyl carbonate afforded ethyl 4,4,4-trichloro-1-butenyl carbonate along with a hydrotrichloromethylation product. 2-Methyl-3-trimethylsilyl-1-propene yielded a product based on the addition of a trichloromethyl group followed by hydrogen-elimination from a 2-methyl group.