19752-23-9

Basic information

• Product Name: Cinnamyltrimethylsilane
• Synonyms: Cinnamyltrimethylsilane;Silane, trimethyl(3-phenyl-2-propenyl)-;TRIMETHYL[(2E)-3-PHENYL-2-PROPENYL]SILANE
• CAS NO: 19752-23-9
• Molecular Formula: C₁₂H₁₈Si
• Molecular Weight: 190.35682
• Mol File: 19752-23-9.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Cinnamyltrimethylsilane(CAS DataBase Reference)
• NIST Chemistry Reference: Cinnamyltrimethylsilane(19752-23-9)
• EPA Substance Registry System: Cinnamyltrimethylsilane(19752-23-9)

Safety Data

• Hazardous Substances Data: 19752-23-9(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
Cinnamyltrimethylsilane is used as a synthetic intermediate for the production of various organic compounds, including fragrances, flavors, and pharmaceuticals. Its versatility in organic synthesis is attributed to its unique chemical structure and reactivity.
Used in Fragrance and Flavor Industry:
Cinnamyltrimethylsilane is used as a key component in the synthesis of fragrances and flavors, enhancing the sensory experience of various products. Its unique properties contribute to the development of novel and complex scents and tastes.
Used in Pharmaceutical Industry:
Cinnamyltrimethylsilane is employed as a reagent in the synthesis of pharmaceutical compounds, facilitating the formation of carbon-carbon bonds. Its application in this industry is crucial for the development of new and effective medications.
Used in Organic Reactions:
Cinnamyltrimethylsilane is utilized as a reagent in various organic reactions, particularly in the formation of carbon-carbon bonds. Its unique reactivity allows for the efficient synthesis of complex organic molecules, making it a valuable tool in the field of organic chemistry.

Upstream product

• 21087-29-6 trans-3-phenylprop-2-enyl chloride 
• 75-77-4 chloro-trimethyl-silane 
• 103-54-8 cinnamyl acetate 
• 20605-46-3 3-(benzenesulfonyl)propenylbenzene 
• 100-52-7 benzaldehyde 
• 123159-55-7 <2-(trimethylsilyl)ethyl>tris(2-methylphenyl)phosphonium iodide 
• 2687-12-9 cinnamyl chloride 
• 103-64-0 bromostyrene 
• 13170-43-9 (trimethylsilyl)methylmagnesium chloride 
• 73476-18-3 1-benzenesulfonyl-2-trimethylsilylethane 
• 124475-06-5 2-(Trimethylsilyl)ethyl Phenylacetate 
• 1496617-11-8 2-(trimethylsilyl)ethyl 2-diazo-2-phenylacetate 
• 2916-68-9 2-(Trimethylsilyl)ethanol 
• 1822-00-0 trimethylsilylmethyllithium 

Downstream Products

• 81194-41-4 3,4-diphenyl-4-methyl-1-pentene 
• 637-50-3 1-phenylpropene 
• 14213-84-4 2-phenylethylstyrene 
• 51751-11-2 1,4-diphenyl-1-buten-4-ol 
• 128721-78-8 N-(1-Ethyl-2-phenyl-but-3-enyl)-4-methyl-benzenesulfonamide 
• 128721-81-3 N-(1-Isopropyl-2-phenyl-but-3-enyl)-4-methyl-benzenesulfonamide 
• 170118-13-5 3,4-diethoxy-2-methyl-4-(1-phenyl-2-propenyl)-2-cyclobutenone 
• 1080487-98-4 1-[5-O-benzyl-2,3-O-(3-pentylidene)-β-D-ribofuranosyl]-2-propenylbenzene 
• 81194-40-3 3,4,4-triphenyl-1-butene 
• 1244556-55-5 methoxy 4-(2-phenylbut-3-en-1-yl)benzene 

Relevant articles and documents

A convenient synthesis of z-allylsilanes with good stereoselectivity promoted by samarium diiodide

Synthesis of Z-allylsilanes in high or good yields and with good stereoselectivity is achieved from O-acetylated 1-silyl-3-chloro alcohols promoted by SmI2. The starting compounds were easily prepared from 2-chloroaldehydes and a mechanism is p

TfO-···H-O-H Interaction-Assisted Generation of a Silicon Cation from Allylsilanes: Access to Phenylallyl Ferrier Glycosides from Glycals

We demonstrate here that the strained and bulky protonated 2,4,6-tri-tert-butylpyridine (TTBPy) triflate salt serves as a mild and efficient organocatalyst for the diastereoselective C-Ferrier glycosylation of various glycals. The importance of the role of the 1/2 H2O molecule trapped in the catalyst has been disclosed. The mechanism of action involves unique anionic triflate and H2O hydrogen-bond interactions that assist the activation of allylsilanes, providing unprecedented access to diastereoselective phenylallyl Ferrier glycosides.

Three-Component Visible-Light-Induced Palladium-Catalyzed 1,2-Alkyl Carbamoylation/Cyanation of Alkenes

A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation and cyanation of alkenes was developed. This general transformation, which proceeds via the in situ formation of a reactive ketenimine intermediate, allows for a rapid construction of a broad range of valuable amides and nitriles from readily available alkenes, alkyl iodides, and isocyanides. An efficient synthesis of tetrazole and amidine via this approach was also demonstrated.

Arylboronic Acid Catalyzed C-Alkylation and Allylation Reactions Using Benzylic Alcohols

The arylboronic acid catalyzed dehydrative C-alkylation of 1,3-diketones and 1,3-ketoesters using secondary benzylic alcohols as the electrophile is reported, forming new C-C bonds (19 examples, up to 98% yield) with the release of water as the only byproduct. The process is also applicable to the allylation of benzylic alcohols using allyltrimethylsilane as the nucleophile (12 examples, up to 96% yield).

METHOD FOR PRODUCING ALLYLSILANE COMPOUND UTILIZING PALLADIUM NANOPARTICLE CATALYST

PROBLEM TO BE SOLVED: To provide a method for efficiently producing an allylsilane compound from a substrate being inexpensive and capable of being easily handled in one step without using a large amount of a metal catalyst. SOLUTION: The method for producing an allylsilane compound represented by formula (C) includes a reaction step of reacting an allyl alcohol compound represented by formula (A) and a disilane compound represented by formula (B) in the presence of a palladium nanoparticle catalyst having a coordinating organic compound coordinated to the surface of a palladium nanoparticle and a co-catalyst. (In formulae (A) to (C), R1 to R3 each independently represent a hydrogen atom, a 1-20C aliphatic hydrocarbon group, a 6-20C aromatic hydrocarbon group or a 3-20C aromatic heterocyclic group; R4 and R5 each independently represent a hydrogen atom, 1-20C aliphatic hydrocarbon group, a 6-20C aromatic hydrocarbon group or a 3-20C aromatic heterocyclic group; and R6 to R8 each independently represent a hydrogen atom, a halogen atom, a 1-20C aliphatic hydrocarbon group or a 6-20C aromatic hydrocarbon group.) SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT

Energy Transfer from CdS QDs to a Photogenerated Pd Complex Enhances the Rate and Selectivity of a Pd-Photocatalyzed Heck Reaction

This Article describes the design of a colloidal quantum dot (QD) photosensitizer for the Pd-photocatalyzed Heck coupling of styrene and iodocyclohexane to form 2-cyclohexylstyrene. In the presence of 0.05 mol % CdS QDs, which have an emission spectrum that overlaps the absorption spectrum of a key Pd(II)alkyl iodide intermediate, the reaction proceeds with 82% yield for the Heck product at 0.5 mol % loading of Pd catalyst; no product forms at this loading without a sensitizer. A radical trapping experiment and steady-state and transient optical spectroscopies indicate that the QDs transfer energy to a Pd(II)alkyl iodide intermediate, pushing the reaction toward a Pd(I) alkyl radical species that leads to the Heck coupled product, and suppressing undesired β-hydride elimination directly from the Pd(II)alkyl iodide. Functionalization of the surfaces of the QDs with isonicotinic acid increases the rate constant of this reaction by a factor of 2.4 by colocalizing the QD and the Pd-complex. The modularity and tunability of the QD core and surface make it a convenient and effective chromophore for this alternative mode of cooperative photocatalysis.

Regioselectivity of Stoichiometric Metathesis of Vinylsilanes with Second-Generation Grubbs Catalyst: A Combined DFT and Experimental Study

The regioselectivity of metathesis reactions of trisubstituted vinylsilanes H2C=CHSiR3 (SiR3 = SiCl3, SiCl2Me, SiClMe2, SiMe3, Si(OEt)3) with the second-generation rut

Palladium-Catalyzed Oxidative Silylation of Simple Olefins To Give Allylsilanes Using Hexamethyldisilane and Molecular Oxygen as the Sole Oxidant

A Pd-catalyzed oxidative silylation of simple olefins with hexamethyldisilane to give allylsilanes has been achieved using molecular oxygen as the sole oxidant. The reaction provides a useful protocol to access synthetically useful allylsilanes from easil

Palladium-catalyzed C(sp 3)-C(sp 2) cross-coupling of (trimethylsilyl)methyllithium with (hetero)aryl halides

The palladium-catalyzed direct cross-coupling of a range of organic chlorides and bromides with the bifunctional C(sp3)-(trimethylsilyl)methyllithium reagent is reported. The use of Pd-PEPPSI-IPent as the catalyst allows for the preparation of structurally diverse and synthetically versatile benzyl- and allylsilanes in high yields under mild conditions (room temperature) with short reaction times.

Catalysis and chemodivergence in the interrupted, formal homo-nazarov cyclization using allylsilanes

A chemodivergent, Lewis acid catalyzed allylsilane interrupted formal homo-Nazarov cyclization is disclosed. With catalytic amounts of SnCl4 and in the presence of allyltrimethylsilane, a formal Hosomi-Sakurai-type allylation of the oxyallyl cation intermediate is observed. A variety of functionalized donor-acceptor cyclopropanes and allylsilanes were shown to be amenable to the reaction transformation and the allyl products were formed in up to 92% yield. Under dilute reaction conditions with stoichiometric SnCl4 and at reduced temperatures, an unusual formal [3 + 2]-cycloaddition between the allylsilane and the oxyallyl cation occurred to give hexahydrobenzofuran products in up to 69% yield.