14630-40-1 | Bis(trimethylsilyl)acetylene

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$10.00	$7.00
5g	98%	in stock	$13.00	$9.00
10g	98%	in stock	$18.00	$12.00
25g	98%	in stock	$22.00	$15.00
50g	98%	in stock	$39.00	$27.00
100g	98%	in stock	$70.00	$49.00

Description

• Catalog Number: AA64436
• Chemical Name: Bis(trimethylsilyl)acetylene
• CAS Number: 14630-40-1
• Molecular Formula: C8H18Si2
• Molecular Weight: 170.3995
• MDL Number: MFCD00008276
• SMILES: C[Si](C#C[Si](C)(C)C)(C)C

Computed Properties

• Complexity: 149
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Rotatable Bond Count: 2

Upstream Synthesis Route

Bis(trimethylsilyl)acetylene, also known as BTMSA, is a versatile chemical reagent commonly used in organic synthesis. Due to its unique structure and properties, BTMSA finds applications in a wide range of chemical reactions and transformations.One key application of BTMSA in chemical synthesis is its role as a highly efficient acetylene source. Its reactive triple bond enables it to participate in various reactions such as Sonogashira coupling, Cadiot-Chodkiewicz cross-coupling, and various other transformations that involve acetylene intermediates. Additionally, the trimethylsilyl groups flanking the acetylene functionality serve to stabilize the molecule and control its reactivity, allowing for selective and controlled reactions.Moreover, BTMSA can act as a masked acetylene, which means that under certain conditions, the trimethylsilyl groups can be cleaved off to release free acetylene. This feature provides a strategic advantage in synthesis, particularly in cases where direct use of acetylene may be challenging due to safety concerns or reactivity issues.Overall, Bis(trimethylsilyl)acetylene is a valuable tool in the toolbox of organic chemists, offering a versatile and selective approach to incorporating acetylene functionality into complex molecules and facilitating the synthesis of a wide variety of organic compounds.

Literature

• Room-temperature dissociation of 1,2-dibromodisilenes to bromosilylenes.

  Journal of the American Chemical Society 20111214

• (Butane-1,3-diyne-1,4-diyl)bis-(tri-isopropyl-silane).

  Acta crystallographica. Section E, Structure reports online 20100801

• C-H...pi interactions in cocrystals of bis(trimethylsilyl)acetylene and diphenylacetylene with benzene.

  Acta crystallographica. Section C, Crystal structure communications 20100401

• Combination of spectroscopic methods: in situ NMR and UV/Vis measurements to understand the formation of group 4 metallacyclopentanes from the corresponding metallacyclopropenes.

  Journal of the American Chemical Society 20090401

• Di-μ-bromido-tris-(triphenyl-phosphine)-1κP,2κP-disilver(I) tetra-hydro-furan 0.85-solvate.

  Acta crystallographica. Section E, Structure reports online 20090401

• Rhodium-catalyzed anti selective cross-addition of bis(trimethylsilyl)acetylene to diarylacetylenes via carbon-silicon bond cleavage.

  Organic letters 20080501

• Shape-persistent macrocycles with intraannular alkyl groups: some structural limits of discotic liquid crystals with an inverted structure.

  Beilstein journal of organic chemistry 20080101

• Regio- and stereoselective cross-coupling of tert-propargyl alcohols with bis(trimethylsilyl)acetylene and its utilization in constructing a fluorescent donor-acceptor system.

  Organic letters 20070524

• Tandem Si-C and C-H activation for decamethylhafnocene and bis(trimethylsilyl)acetylene.

  Angewandte Chemie (International ed. in English) 20070101

• C-H-Activated aluminum hydroxide via molecular oxygen.

  Inorganic chemistry 20060306

• Reaction of ruthenium ethyne-1,2-diyl compounds with bis(trimethylsilyl)acetylene complexes of titanocene and zirconocene: remarkable transfer of a C2 ligand.

  Angewandte Chemie (International ed. in English) 20050513

• Reactions of titanium and zirconium derivatives of Bis(trimethylsilyl)acetylene with Tris(pentafluorophenyl)borane: a titanium(III) complex of an alkynylboranate.

  Angewandte Chemie (International ed. in English) 20030328