Silican-protected group Application
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Trimethylsilylacetylene

Silican-protected group Application
Trimethylsilylacetylene Structure
Trimethylsilylacetylene
  • CAS No.1066-54-2
  • Chemical Name:Trimethylsilylacetylene
  • CBNumber:CB3175930
  • Molecular Formula:C5H10Si
  • Formula Weight:98.22
  • MOL File:1066-54-2.mol
Trimethylsilylacetylene Property
  • 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 Gravity :0.695
  • Water Solubility  :reacts
  • Hydrolytic Sensitivity :4: no reaction with water under neutral conditions
  • BRN  :906752
  • InChIKey :CWMFRHBXRUITQE-UHFFFAOYSA-N
  • CAS DataBase Reference :1066-54-2(CAS DataBase Reference)
  • NIST Chemistry Reference :(Trimethylsilyl)acetylene(1066-54-2)
  • EPA Substance Registry System :Trimethylsilylacetylene (1066-54-2)
Safety
  • 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
  • NFPA 704:
    3
    1 0
Hazard and Precautionary Statements (GHS)
  • Symbol(GHS)
  • Signal wordDanger
  • Hazard statements H225-H315-H319
  • Precautionary statements P210-P305+P351+P338-P370+P378-P403+P235-P240-P241-P280a-P303+P361+P353-P501a
Trimethylsilylacetylene Price More Price(15)
  • Brand: Sigma-Aldrich
  • Product number: 218170
  • Product name : Ethynyltrimethylsilane
  • Purity: 98%
  • Packaging: 5g
  • Price: $57.2
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 8.14226
  • Product name : Trimethylsilylacetylene
  • Purity: for synthesis
  • Packaging: 5 mL
  • Price: $57.81
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: Sigma-Aldrich
  • Product number: 218170
  • Product name : Ethynyltrimethylsilane
  • Purity: 98%
  • Packaging: 1g
  • Price: $29.6
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: T1239
  • Product name : Trimethylsilylacetylene
  • Purity: >98.0%(GC)
  • Packaging: 5mL
  • Price: $34
  • Updated: 2021/03/22
  • Buy: Buy
  • Brand: TCI Chemical
  • Product number: T1239
  • Product name : Trimethylsilylacetylene
  • Purity: >98.0%(GC)
  • Packaging: 25mL
  • Price: $101
  • Updated: 2021/03/22
  • Buy: Buy

Trimethylsilylacetylene Chemical Properties,Usage,Production

  • Silican-protected group Trimethylsilylacetylene 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 Properties CLEAR COLORLESS LIQUID
  • Physical properties bp 53 °C; d 0.695 g cm?3.
  • Uses Trimethylsilylacetylene 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.
  • Uses Ethynyltrimethylsilane 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 Methods Distil 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
Raw materials
Preparation Products
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  • 1066-54-2
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  • CH33SiCCH
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  • HCCSiCH33
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  • Building Blocks
  • Terminal
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