Bis(trimethylsilyl)acetylene
Names | |
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Preferred IUPAC name
Ethynediylbis(trimethylsilane) | |
Other names
BTMSA
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Identifiers | |
3D model (
JSmol ) |
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ChemSpider | |
ECHA InfoCard
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100.035.141 |
PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C8H18Si2 | |
Molar mass | 170.402 g·mol−1 |
Appearance | Colorless to white Liquid |
Density | 0.791 g/cm3 |
Melting point | 26 °C (79 °F; 299 K) |
Boiling point | 134.6 ± 8.0 °C |
0.031 g/L | |
Hazards | |
Occupational safety and health (OHS/OSH): | |
Main hazards
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Flammable, Irritant |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Bis(trimethylsilyl)acetylene (BTMSA) is an
soluble in organic solvents. This compound is used as a surrogate for acetylene
.
BTMSA is prepared by treating acetylene with
chlorotrimethylsilane:[1]
- Li2C2 + 2 Me3SiCl → Me3SiC≡CSiMe3 + 2 LiCl
Applications
BTMSA is used as a
Friedel-Crafts type acylations and alkylations and a precursor to lithium trimethylsilylacetylide. The TMS groups can be removed with tetra-n-butylammonium fluoride (TBAF) and replaced with protons. BTMSA is also a useful reagent in cycloaddition reactions. Illustrating its versatility, BTMSA was used in a concise total synthesis of (±)-estrone.[2] A key step in this synthesis was the formation of the steroidal skeleton, catalyzed by CpCo(CO)2
.
BTMSA also serves as a ligand in organometallic chemistry. For example, it forms stable adducts with metallocenes.[3]
- Cp2TiCl2 + Mg + Me3SiC≡CSiMe3 → Cp2Ti[(CSiMe3)2] + MgCl2
BTMSA is also used in the total synthesis of epibatidine (and analogs), and also in the synthesis of iclaprim.
References
- .
- ISBN 978-0471936237.
- .