Bis(trimethylsilyl)acetylene

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Bis(trimethylsilyl)acetylene
Skeletal formula of bis(trimethylsilyl)acetylene
Ball-and-stick model of the bis(trimethylsilyl)acetylene molecule
Names
Preferred IUPAC name
Ethynediylbis(trimethylsilane)
Other names
BTMSA
Identifiers
3D model (
JSmol
)
ChemSpider
ECHA InfoCard
 100.035.141 Edit this at Wikidata
  • InChI=1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3 ☒N
    Key: ZDWYFWIBTZJGOR-UHFFFAOYSA-N ☒N
  • InChI=1/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3
    Key: ZDWYFWIBTZJGOR-UHFFFAOYAF
  • C(#C[Si](C)(C)C)[Si](C)(C)C
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
 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

  1. doi:10.1016/S0022-328X(00)89260-8
    .
  2. ISBN 978-0471936237
    .
  3. doi:10.1021/om0208570
    .
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