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Trimethylsilylacetylene

Basic information Silican-protected group Application Safety Related Supplier
Trimethylsilylacetylene Basic information
Trimethylsilylacetylene Chemical Properties
  • Melting point:>0°C
  • Boiling point:53 °C(lit.)
  • Density 0.695 g/mL at 25 °C(lit.)
  • vapor pressure 4.18 psi ( 20 °C)
  • refractive index n20/D 1.388(lit.)
  • Flash point:<−30 °F
  • storage temp. Store below +30°C.
  • solubility Miscible with organic solvents.
  • form liquid
  • color colorless
  • Specific Gravity0.695
  • Water Solubility reacts
  • Hydrolytic Sensitivity4: no reaction with water under neutral conditions
  • BRN 906752
  • InChIKeyCWMFRHBXRUITQE-UHFFFAOYSA-N
  • CAS DataBase Reference1066-54-2(CAS DataBase Reference)
  • NIST Chemistry Reference(Trimethylsilyl)acetylene(1066-54-2)
  • EPA Substance Registry SystemTrimethylsilylacetylene (1066-54-2)
Safety Information
  • Hazard Codes F,Xi
  • Risk Statements 11-36/37/38
  • Safety Statements 16-26-36
  • RIDADR UN 1993 3/PG 2
  • WGK Germany -
  • Hazard Note Flammable/Irritant
  • TSCA T
  • HazardClass 3
  • PackingGroup II
  • HS Code 29310095
MSDS
Trimethylsilylacetylene Usage And Synthesis
  • Silican-protected groupTrimethylsilylacetylene is a silican-protected group, also known as trimethylethynylsilane, trimethylethynyl silicon and ethynyltrimethylsilane. It is a colorless transparent liquid at room temperature. It could be used to synthesize parazole by the addition of 1,3-bipolar ring of acetylene diazide. It is also the substrate of nickel catalyzed reaction and benzonitrile coupling reaction.
  • Application
    • Common intermediate for asymmetric synthesis
    • Silica reagent
  • Chemical PropertiesCLEAR COLORLESS LIQUID
  • Physical propertiesbp 53 °C; d 0.695 g cm?3.
  • UsesTrimethylsilylacetylene is a valuable reagent used in ethynylation by palladium(0)-catalyzed coupling/condensation with aryl and vinyl halides and triflates, or by nucleophilic attack of the corresponding acetylide on electrophilic centers; reacts with alkyl iodides, tin hydrides,6 and dichloroketene in a regioselective and stereoselective manner, participating in the following synthesis reactions: Ethynylations, Palladium(0)-Catalyzed Coupling Reactions,Reaction of Trimethylsilylacetylides with Electrophiles, Radical-Initiated and Transition Metal-Catalyzed Additions, Cycloaddition Reactions, Ethynylations, Cycloaddition Reactions, Further Transformations etc.
  • UsesEthynyltrimethylsilane was used in: ? microwave-assisted, one-pot, three-step Sonogashira cross-coupling-desilylation-cycloaddition reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles synthesis of poly(ethynyltrimethylsilane) containing Pd (II) coordination sites pyrazole synthesis via 1,3-dipolar cycloaddition of diazo compounds to acetylenes
  • Purification MethodsDistil it through an efficient column. The IR has bands at max 2041 (CC) and 3289 (C-H) cm-1. [Kr.hnke & Goss Chem Ber 92 30 1959, Beilstein 4 IV 3937.]
Trimethylsilylacetylene Preparation Products And Raw materials
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