129541-12-4

Basic information

• Product Name: Silane, triethyl[[(2E)-3-phenyl-2-propenyl]oxy]-
• CAS NO: 129541-12-4
• Molecular Formula: C15H24OSi
• Molecular Weight: 248.44
• Mol File: 129541-12-4.mol

Chemical Properties

• CAS DataBase Reference: Silane, triethyl[[(2E)-3-phenyl-2-propenyl]oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: Silane, triethyl[[(2E)-3-phenyl-2-propenyl]oxy]-(129541-12-4)
• EPA Substance Registry System: Silane, triethyl[[(2E)-3-phenyl-2-propenyl]oxy]-(129541-12-4)

Safety Data

• Hazardous Substances Data: 129541-12-4(Hazardous Substances Data)

Upstream product

• 617-86-7 triethylsilane 
• 104-55-2 3-phenyl-propenal 
• 994-30-9 triethylsilyl chloride 
• 4407-36-7 (2E)-3-phenyl-2-propen-1-ol 
• 14371-10-9 (E)-3-phenylpropenal 
• 23510-72-7 (2E)-3-phenylprop-2-en-1-yl formate 
• 104-54-1 3-Phenylpropenol 

Downstream Products

• 122-97-4 3-Phenyl-1-propanol 
• 2290-40-6 3-phenylpropanol triethylsilyl ether 
• 1428137-69-2 (E)-3-phenyl-1-(triethylsilyl)prop-2-en-1-ol 
• 110659-58-0 (1R,2R)-1-hydroxymethyl-2-phenylcyclopropane 

Relevant articles and documents

Hydrosilylation of unsaturated (hetero)aromatic aldehydes and related compounds catalyzed by transition metal complexes

[Rh(COD)CI]2 has been found to be a more active catalyst than Ir, Ru, Pt and Pd complexes for the hydrosilylation of unsaturated furan and aromatic aldehydes with HSiEt3. 1,4- and 1,2-addition reactions giving unsaturated silyl ethers in cis- and trans-configurations occurred as well as the hydrogenation reactions which produce the corresponding saturated silyl ethers. The migration of the ethyl group was observed in the hydrosilylation of 3-ethyl-3-(5-nitrofuryl)acrolein. The dehydrogenative silylation occurred in the reactions of cinnamyl alcohol and furan-2-acrylic acid.

Use of Silylated Formiates as Hydrosilane Equivalents

The present invention relates to a method for preparing organic compounds of formula (I) by reaction between a silylated formiate of formula (II) and an organic compound in the presence of a catalyst and optionally of an additive. The invention also relates to use of the method for preparing organic compounds of formula (I) for the preparation of reagents for fine chemistry and for heavy chemistry, as well as in the production of vitamins, pharmaceutical products, adhesives, acrylic fibres, synthetic leathers, and pesticides.

Synergistic Catalysis by Br?nsted Acid/Carbodicarbene Mimicking Frustrated Lewis Pair-Like Reactivity

Carbodicarbene (CDC), unique carbenic entities bearing two lone pairs of electrons are well-known for their strong Lewis basicity. We demonstrate herein, upon introducing a weak Br?nsted acid benzyl alcohol (BnOH) as a co-modulator, CDC is remolded into a Frustrated Lewis Pair (FLP)-like reactivity. DFT calculation and experimental evidence show BnOH loosely interacting with the binding pocket of CDC via H-bonding and π-π stacking. Four distinct reactions in nature were deployed to demonstrate the viability of proof-of-concept as synergistic FLP/Modulator (CDC/BnOH), demonstrating enhanced catalytic reactivity in cyclotrimerization of isocyanate, polymerization process for L-lactide (LA), methyl methacrylate (MMA) and dehydrosilylation of alcohols. Importantly, the catalytic reactivity of carbodicarbene is uniquely distinct from conventional NHC which relies on only single chemical feature of nucleophilicity. This finding also provides a new spin in diversifying FLP reactivity with co-modulator or co-catalyst.

Hydrosilylation of Carbonyls Catalyzed by Hydridoborenium Borate Salts: Lewis Acid Activation and Anion Mediated Pathways

The electronically unsaturated three-coordinated hydridoborenium cations [LBH]+[HB(C6F5)3]-(1) and [LBH]+[B(C6F5)4]-(2), supported by a bis(phosphinimino)amide ligand, were found to be excellent catalysts for hydrosilylation of a range of aliphatic and ar

Electrophilic Organobismuth Dication Catalyzes Carbonyl Hydrosilylation

Bismuth compounds are gaining importance as potential alternatives to transition-metal complexes and electron deficient lighter p-block compounds in homogeneous catalysis. Computational analysis on the two-coordinate [(Me2NC6H4)Bi]2+ possessing three electrophilic sites is experimentally evidenced by the isolation of [{Me2NC6H4}Bi{OP(NMe2)3}3][B(3,5-C6H3Cl2)4]2. These observations led us to generate dicationic organobismuth catalyst, [(Me2NC6H4)Bi(L)3]2+ (L=aldehyde/ketone), evidenced by NMR spectroscopy in solution and by single-crystal X-ray diffraction in the solid state. It efficiently catalyzes hydrosilylation of aldehydes and ketones resulting in silyl ethers as the only products in high yields. Our investigations support a carbonyl activation mechanism at the bismuth center followed by Si?H addition.

Mild synthesis of silyl ethers: Via potassium carbonate catalyzed reactions between alcohols and hydrosilanes

A method has been developed for the silanolysis of alcohols using an abundant and non-corrosive base K2CO3 as a catalyst. Reactions between a variety of alcohols and hydrosilanes generate silyl ethers under mild conditions. The use of hydrosilanes leads to the formation of H2 as the only byproduct thus avoiding the formation of stoichiometric strong acids. The mild conditions lead to a wide scope of possible alcohol substrates and good functional group tolerance. Selective alcohol silanolysis is also observed in the presence of reactive C-H bonds, lending this method for extensive use in protection group chemistry.

N-Heterocyclic Olefin Catalyzed Silylation and Hydrosilylation Reactions of Hydroxyl and Carbonyl Compounds

N-Heterocyclic olefins (NHOs), the alkylidene derivatives of N-heterocyclic carbenes (NHCs), have recently emerged as a new family of promising organocatalysts with strong nucleophilicity and Br?nsted basicity. The development of a novel method is shown using NHOs as efficient promoters for the direct dehydrogenative silylation of alcohols or hydrosilylation of carbonyl compounds. Preliminary results of the first NHO-promoted asymmetric synthesis are also discussed.

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.

Large-scale preparation and labelling reactions of deuterated silanes

A catalytic synthesis of deuterated silanes SiEt3D, SiMe 2PhD and SiPh2D2 is reported that allows their facile generation in a 3-4g scale, utilizing D2 (0.5bar) as the hydrogen isotope source and low

Controlled hydrosilylation of carbonyls and imines catalyzed by a cationic aluminum alkyl complex

The synthesis, characterization, and unprecedented catalytic activity of cationic aluminum alkyl complexes toward hydrosilylation are described. X-ray crystallographic analysis of Tp*AlMe2 (1) and [Tp*AlMe][I3] (3) revealed the prefe