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Bis(trimethylsilyl)acetylene

Catalog No. A11960 Name Alfa Aesar
CAS Number 14630-40-1 Website
M. F. C8H18Si2 Telephone
M. W. 170.39952 Fax
Purity 99% Email
Storage Chembase ID: 126168

SYNONYMS

Title
双(三甲基硅基)乙炔
IUPAC name
trimethyl[2-(trimethylsilyl)ethynyl]silane
IUPAC Traditional name
bis(trimethylsilyl)acetylene
Synonyms
BSTMA

DATABASE IDS

Beilstein Number 906870
MDL Number MFCD00008276
CAS Number 14630-40-1
EC Number 238-671-9

PROPERTIES

Purity 99%
Boiling Point 134-136°C
Density 0.770
Flash Point 2°C(35°F)
Melting Point 20-24°C
Refractive Index 1.4270
GHS Pictograms GHS02
GHS Hazard statements H226
GHS Precautionary statements P210-P261
Risk Statements 10
Safety Statements 16
TSCA Listed
Hazard Class 3
UN Number UN1993
Packing Group III

DETAILS

REFERENCES

  • Precursor of lithium TMS acetylide: J. Chem. Soc., Chem. Commun., 840 (1979), and dilithioacetylide: Tetrahedron Lett., 34, 839 (1993).
  • Reacts with electrophiles via Si-stabilized carbocations ions and subsequent desilylation; see Appendix 4. Thus, Lewis acid promoted reaction with acid chlorides gives alkynyl ketones, leading to a synthesis of ɑ?-enals: J. Org. Chem., 38, 2254 (1973); 57, 3203 (1992):
  • Addition to chiral acetals in the presence of TiCl4 leads to ɑ-hydroxy alkynes in high yield and ee: J. Am . Chem. Soc., 105, 2904 (1983); J. Chem. Soc., Perkin 1, 3301 (1991). Sulfonyl chlorides give alkynyl sulfones: Org. Synth. Coll., 8, 281 (1993), and references therein.