Chemical Property of (TRIISOPROPYLSILYL)ACETYLENE
Chemical Property:
- Appearance/Colour:clear colorless liquid
- Vapor Pressure:0.0981mmHg at 25°C
- Melting Point:50-51 °C
- Refractive Index:n20/D 1.4527(lit.)
- Boiling Point:230.746 °C at 760 mmHg
- Flash Point:56.111 °C
- PSA：0.00000
- Density:0.79 g/cm3
- LogP:3.83760
- Storage Temp.:under inert gas (nitrogen or Argon) at 2-8°C
- Solubility.:Miscible with organic solvents.
- Hydrogen Bond Donor Count:0
- Hydrogen Bond Acceptor Count:0
- Rotatable Bond Count:4
- Exact Mass:182.149077236
- Heavy Atom Count:12
- Complexity:159
- Purity/Quality:
-
99% *data from raw suppliers
Triisopropylsilylacetylene *data from reagent suppliers
Safty Information:
- Pictogram(s):
Xi
- Hazard Codes:Xi
- Statements:
36/37/38
- Safety Statements:
26-36/37/39-37/39
- MSDS Files:
-
SDS file from LookChem
Useful:
- Canonical SMILES:CC(C)[Si](C#C)(C(C)C)C(C)C
-
Physical properties
colorless clear liquid; bp 50–52 °C at 0.8 hPa
(0.6 mmHg), flash point 56 °C (closed cup); d = 0.813.
-
Uses
(Triisopropylsilyl)acetylene may be used as reagent for the rhodium-catalyzed asymmetric alkynylation of various α,β-unsaturated ketones. It may be used as reagent in the enantioselective synthesis of β-alkynylated nitroalkanes. (Triisopropylsilyl)acetylene (TIPS-acetylene) is an
easily handled and inexpensive monoprotected acetylene used
as an attractive substitute for trimethylsilylacetylene (TMSacetylene).
The bulkier silyl protecting group of TIPS-acetylene
provides stability in a wider range of reaction conditions than
TMS-acetylene. Its higher boiling point also provides better handling
and safety than TMS-acetylene (bp 87–88°C at 12 hPa
(9 mmHg)). The general utility of TIPS-acetylene is often highlighted
in the transition metal-catalyzed C–C bond formations， including but not limited to transition metal-catalyzed Coupling Reactions；Reaction of TIPS-acetylide with Electrophiles；Synthesis of Polyynes；Transition Metal-catalyzed Cross-addition of TIPSacetylene
to Alkynes；Hydroalkynylation；Direct Alkynylation；Conjugate Addition；Cycloaddition；Ring-opening Reactions etc.
