27490-78-4

Usage

Uses

Used in Organic Synthesis:
Trimethyl(2-phenylethyl)stannane is used as a reagent in organic synthesis for facilitating Stille coupling reactions, which are cross-coupling reactions between an organotin compound and an organohalide to form carbon-carbon bonds. This application is crucial for the synthesis of complex organic molecules and pharmaceuticals.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, trimethyl(2-phenylethyl)stannane is utilized as a precursor in the synthesis of various drugs and medicinal compounds. Its role in Stille coupling reactions allows for the creation of specific molecular structures that are otherwise difficult to achieve, contributing to the development of new therapeutic agents.
However, due to its toxic nature and potential health risks, including skin and eye irritation, respiratory issues, and carcinogenic effects, trimethyl(2-phenylethyl)stannane must be handled with extreme care. Adequate safety measures and disposal methods are essential to mitigate any adverse effects on human health and the environment.

Upstream product

• 17620-97-2 diphenyl-(1-phenylethenyl)phosphine 
• 1631-73-8 trimethylstannane 
• 3277-89-2 phenethylmagnesium bromide 
• 1066-45-1 trimethyltin(IV)chloride 
• 103-63-9 1-phenyl-2-bromoethane 
• 97664-45-4 β-phenethyldimethyltin bromide 
• 124-41-4 sodium methylate 

Downstream Products

• 100-42-5 styrene 
• 101-48-4 phenylacetaldehyde dimethyl acetal 
• 35373-47-8 (CH₃)2Sn{CH(CH₃)C₆H₅}(CH₂CH₂C₆H₅) 
• 27490-65-9 (CH₃)3SnCH₂CH(C₆H₅)CHCl₂ 

Relevant academic research and scientific papers

Sila-Reichstoffe und Riechstoffisostere XII. Geruchsvergleiche homologer Organoelementverbindungen der vierten Hauptgruppe (C, Si, Ge, Sn)

Homologous compounds of the linalool type R(CH3)2El-OH (with R=C6H5CH2 and C6H5CH2CH2) as well as their derivatives R(CH3)2El-OCH3 and 2O show, in dependence of El=C, Si, Ge and Sn partly similar, but sometimes very different characteristics of odor.Unexpected are high qualities of fragrance with El=Ge, whereas derivatives with El=Sn remain scentless, obviously owing to polymerization.Noteworthy are the strong differences of odor in the system C6H5CH2El(CH3)3 from C via Si and Ge up to Sn, standing fully contrary to the postulation of Amoore whereupon smell qualities are only controlled by size and shape of molecules.C6H5CH2Sn(CH3)2OH(A1Sn) crystallizes as poly-μ-hydroxo-benzyldimethyltin with an one dimensional Sn-O-Sn-O chain (Sn-O 2.17(9) and 2.29(9) Angstroem) in the monoclinic space group C2 (a=12.696(4), b=4.181(2), c=10.626(3) Angstroem and β=106.8(3) deg).

Stannylated phosphines. I. Preparation of (β-trimethylstannyl)alkyldiphenylphosphines

(β-Trimethylstannyl)alkyldiphenylphosphines can be readily prepared by addition of diphenylphosphine to the corresponding vinyltrimethyltin Me3SnCR=CH2 under free radical conditions.In contrast, free radical hydrostannation of the corresponding phosphines Ph2PCR=CH2 is a more complex process, and is apparently of little synthetic value.The title compound can be easily oxidised by potassium permanganate to give the corresponding phosphine oxides in good yields.Hydrostannation of model alkynyldiphenylphosphines (RCCPPh2, R=H, Me3Sn) occurs regiospecifically.