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14630-40-1 - Bis(trimethylsilyl)acetylene, 99% - BSTMA - A11960 - Alfa Aesar

A11960 Bis(trimethylsilyl)acetylene, 99%

CAS Number
14630-40-1
Synonyms
BSTMA

Size Price ($) Quantity Availability
10g 47.34
50g 153.60
250g 620.00
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Bis(trimethylsilyl)acetylene, 99%

MDL
MFCD00008276
EINECS
238-671-9

Chemical Properties

Formula
C8H18Si2
Formula Weight
170.40
Melting point
20-24°
Boiling Point
134-136°
Flash Point
2°(35°F)
Density
0.770
Refractive Index
1.4270
Solubility
Not miscible or difficult to mix in water. Soluble in Chloroform and Methanol.

Applications

BTMSA is used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It is also used in the synthesis of (+)-brasilenyne2 and (β-diketanato)Ag(BTMSA). Bis(trimethylsilyl)acetylene is a ligand that binds to a central metal ion (e.g. Titanium) to create a coordination complex. One of its complexes, Permethyltitanocene-bis(trimethylsilyl)acetylene, is a catalyst for the head-to-tail dimerization of 1-alkynes (e.g. 3-Penten-1-yne [P227430]).

Notes

Store away from oxidizing agents. Do not store together with acids.

Literature References

Christian Reus.; Liu NW.; Bolte M.; Lerner HW.; Wagner M. Synthesis of bromo-, boryl-, and stannyl-functionalized 1,2-bis(trimethylsilyl)benzenes via Diels-Alder or C-H activation reactions.J. Org. Chem.,2012,77(7), 3518-3523.

Denmark SE.; Yang SM. Intramolecular silicon-assisted cross-coupling: total synthesis of (+)-brasilenyne.J Am Chem Soc.,2002,124(51), 15196-15197.

Akinobu Horita.; Hayato Tsurugi.; Tetsuya Satoh.; Masahiro Miura. IRhodium-catalyzed anti selective cross-addition of bis(trimethylsilyl)acetylene to diarylacetylenes via carbon-silicon bond cleavage.Org Lett.,2008,10(9), 1751-1754.

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 ɑß-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.

Precursor of lithium TMS acetylide: J. Chem. Soc., Chem. Commun., 840 (1979), and dilithioacetylide: Tetrahedron Lett., 34, 839 (1993).

GHS Hazard and Precautionary Statements

Hazard Statements: H226

Flammable liquid and vapour.

Precautionary Statements: P210-P261

Keep away from heat/sparks/open flames/hot surfaces. - No smoking. Avoid breathing dust/fume/gas/mist/vapours/spray.

Other References

Beilstein
906870
Hazard Class
3
Packing Group
III
Harmonized Tariff Code
2931.90
TSCA
Yes

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