CAS 1066-54-2: (Trimethylsilyl)acetylene

(Trimethylsilyl)acetylene is used in the preparation of trimethylsilanyl-propiolic acid ethyl ester by reacting with carbonochloridic acid ethyl ester as well as in the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides. It is used as a nucleophile in Friedel-Crafts type acylations and alkylations reactions, as a ligand in organometallic chemistry and an useful reagent in cycloaddition reactions. It acts as a precursor to lithium trimethylsilylacetylide It finds application in the synthesis of (±)-estrone. This Thermo Scientific Chemicals brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

S18950 - Trimethylsilylacetylene

This Thermo Scientific Chemicals brand product was originally part of the Acros Organics product portfolio. Some documentation and label information may refer to the legacy brand. The original Acros Organics product / item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific Chemicals.

Applications Ethynyltrimethylsilane is used in the production of novel histone deacetylase inhibitors for the treatment of Freidreich’s ataxia. It also aids in the preparation of conjugated polymers with sn anthracene backbone. Not a dangerous good if item is equal to or less than 1g/ml and there is less than 100g/ml in the package References Xu, C. et al.: Pharmaceu. 4, 1578 (2011); Kobayashi, E. et al.: J. Polym. Sci. Part A: Polym. Chem., 28, 2641 (1990);

Trimethylsilylacetylene is a chemical compound that belongs to the class of organic compounds. It is an intermediate in the production of fatty acids and has been shown to be involved in the metabolism of other compounds, such as halides. Trimethylsilylacetylene is also used to inhibit inflammatory diseases and metabolic disorders, such as diabetes mellitus and Alzheimer's disease. Trimethylsilylacetylene inhibits replication by binding to the amine group on purine bases or DNA at the replication fork. This prevents DNA synthesis, which prevents cell division, causing cells to die. Trimethylsilylacetylene also inhibits cell division by reacting with carbonyl groups on proteins during replication.

(Trimethylsilyl)acetylene

Alkynylsilane 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. Ethynyltrimethylsilane; Trimethylsilylacetylene Vapor pressure, 20 °C: 214 mmUseful in Sonogashira reactions with differentiated reactivity at each terminus leading to unsymmetrical diaryl acetylenesReacts with aryl aldehydes to give diethynylmethanes (1,4-diynes)Doped polymer films are conductiveEthynylates aromatic compoundsPrecursor to trimethylsilylethynyl copper reagentLithiated derivative (n-BuLi treatment) reacts with halotriazines to produce monomersEmployed in ortho ethenylation of phenolsUndergoes Diels-Alder reactions with butadienesConverts imines to propargyl aminesForms propargylic amines from aldehydes and amines in aqueous systemRegioselectively forms either regioisomeric enyne upon addition to propargyl amines depending on catalyst employedReacts with aryl aldehydes to form diethynylmethane derivativesUseful in the preparation of unsymmetrical diarylacetylenesExtensive 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