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399264 Sigma-Aldrich

(tert-Butyldimethylsilyl)acetylene

99%

Synonym: Ethynyl-tert-butyldimethylsilane

  • CAS Number 86318-61-8

  • Linear Formula (CH3)3CSi(CH3)2C≡CH

  • Molecular Weight 140.30

  •  Beilstein/REAXYS Number 1921466

  •  MDL number MFCD00191877

  •  PubChem Substance ID 24864798

  •  NACRES NA.22

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Properties

Related Categories Alkynes, Building Blocks, Chemical Synthesis, Organic Building Blocks, Terminal More...
assay   99%
refractive index   n20/D 1.451 (lit.)
bp   116-117 °C (lit.)
density   0.751 g/mL at 25 °C (lit.)
SMILES string   CC(C)(C)[Si](C)(C)C#C
InChI   1S/C8H16Si/c1-7-9(5,6)8(2,3)4/h1H,2-6H3
InChI key   RTYNRTUKJVYEIE-UHFFFAOYSA-N

Description

General description

(tert-Butyldimethylsilyl)acetylene is a bulky trialkylsilyl-protected alkyne. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes.

(tert-Butyldimethylsilyl)acetylene readily undergoes cross-dimerization reaction with various internal phenyl acetylenes in the presence of rhodium dimers and bidentate phosphine ligands to afford enynes.

Application

(tert-Butyldimethylsilyl)acetylene may be used in the synthesis of β-alkynylketone and β-alkynyl aldehydes.

Packaging

1, 5 g in ampule

Safety & Documentation

Safety Information

Symbol 
GHS02  GHS02
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
UN 1993BF 3 / PGII
WGK Germany 
WGK 3
Flash Point(F) 
42.8 °F - closed cup
Flash Point(C) 
6 °C - closed cup

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Protocols & Articles

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Peer-Reviewed Papers
15

References

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