Bis(Trimethylsilyl)Acetylene

• CAS: 14630-40-1
• Catalog Number: ACM14630401
• Category: Alkynes
• Molecular Weight: 170.4 g/mol
• Molecular Formula: C8H18Si2
• Synonyms: BSTMA
• IUPAC Name: trimethyl(2-trimethylsilylethynyl)silane
• Canonical SMILES: C[Si](C)(C)C#C[Si](C)(C)C
• InChI Key: ZDWYFWIBTZJGOR-UHFFFAOYSA-N
• Boiling Point: 134.6 °C(760 mmHg)
• Melting Point: 21-24 °C
• Flash Point: 17.1 °C
• Density: 0.791 g/mL
• Appearance: White or Colorless to Almost white or Almost colorless powder to lump to clear liquid
• Application: Bis(trimethylsilyl)acetylene serves multiple functions as both a starting reagent and a ligand It facilitates the synthesis of functionalized 4-R-12-bis(trimethylsilyl)benzenes and specialized compounds like (+)-brasilenyne and (β-diketanato)Ag(BTMSA) This compound is pivotal in the creation of coordination complexes by binding to central metal ions such as titanium forming catalysts like Permethyltitanocene-bis(trimethylsilyl)acetylene which aids in the head-to-tail dimerization of 1-alkynes It acts as a nucleophile in Friedel-Crafts type acylations and alkylations and participates in rhodium-catalyzed addition reactions with diarylacetylenes Notably it undergoes cycloaddition with 15-hexadiynes in the presence of CpCo(CO)2 yielding benzocyclobutenes Additionally its structure is characterized by a center of inversion on its triple bond and it is active in TiCl4-Et2AlCl catalyzed Diels-Alder reactions with norbornadiene
• Storage: Inert atmosphere,2-8 °C
• EC Number: 2386719
• Exact Mass: 170.09500
• Hazard Statements: H315 : Causes skin irritation.; H319 : Causes serious eye irritation.; H228 : Flammable solid.
• MDL Number: MFCD00008276
• Packaging: 10 g; 100 g
• Packing Group: III
• Precautionary Statements: P210-P261-P305+P351+P338
• PubChem ID: 84564
• Refractive Index: 1.426-1.428
• RIDADR: UN 1993C 3 / PGIII
• Safety Description: S16-S26-S36
• Signal Word: Danger
• Stability: Stable under normal temperatures and pressures.
• Symbol: GHS06
• Vapor Density: 9.9 mmHg(25 °C)
• Vapor Pressure: MAY DECOMPOSE
• WGK Germany: 3

Custom Q&A

What is the molecular formula of Bis(trimethylsilyl)acetylene?

The molecular formula is C8H18Si2.

What is the molecular weight of Bis(trimethylsilyl)acetylene?

The molecular weight is 170.40 g/mol.

What is the IUPAC name of Bis(trimethylsilyl)acetylene?

The IUPAC name is trimethyl(2-trimethylsilylethynyl)silane.

What is the InChI of Bis(trimethylsilyl)acetylene?

The InChI is InChI=1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3.

What is the InChIKey of Bis(trimethylsilyl)acetylene?

The InChIKey is ZDWYFWIBTZJGOR-UHFFFAOYSA-N.

What is the canonical SMILES of Bis(trimethylsilyl)acetylene?

The canonical SMILES is C[Si](C)(C)C#C[Si](C)(C)C.

What is the CAS number of Bis(trimethylsilyl)acetylene?

The CAS number is 14630-40-1.

What is the European Community (EC) number of Bis(trimethylsilyl)acetylene?

The EC number is 238-671-9.

What is the heavy atom count of Bis(trimethylsilyl)acetylene?

The heavy atom count is 10.

Is Bis(trimethylsilyl)acetylene a canonicalized compound?

Yes, it is a canonicalized compound.

Synthetic Use

Downstream Synthesis Route 1

• 35207-75-1
• 14630-40-1

• 541-16-2
• 102127-46-8

Reference: [1] Synthesis, 1985, # 9, p. 871 - 873

Downstream Synthesis Route 2

• 73183-34-3
• 14630-40-1

• 178106-81-5
• 178106-85-9
• 159087-46-4

Reference: [1] Organometallics, 1996, vol. 15, # 24, p. 5137 - 5154
[2] Organometallics, 1996, vol. 15, # 24, p. 5137 - 5154

Downstream Synthesis Route 3

• 14630-40-1

• 18163-47-8

Reference: [1] Journal of Organometallic Chemistry, 1989, vol. 372, p. 183 - 186

Downstream Synthesis Route 4

• 79-03-8
• 14630-40-1

• 18387-58-1

Reference: [1]Ungeheuer, Felix; Fürstner, Alois
[Chemistry - A European Journal, 2015, vol. 21, # 32, p. 11387 - 11392]

Downstream Synthesis Route 5

• 75-36-5
• 14630-40-1

• 5930-98-3

Reference: [1]Maurette, Luc; Tedeschi, Christine; Sermot, Emmanuelle; Soleilhavoup, Michle; Hussain, Fatima; Donnadieu, Bruno; Chauvin, Remi
[Tetrahedron, 2004, vol. 60, # 44, p. 10077 - 10098]

Downstream Synthesis Route 6

• 79-04-9
• 14630-40-1

• 18245-82-4

Reference: [1]Bulletin de la Societe Chimique de France,1981,vol. 2,p. 7 - 13

* For details of the synthesis route, please refer to the original source to ensure accuracy.