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187437 Sigma-Aldrich

Bis(trimethylsilyl)acetylene

99%

Synonym: BTMSA

  • CAS Number 14630-40-1

  • Linear Formula (CH3)3SiC≡CSi(CH3)3

  • Molecular Weight 170.40

  •  Beilstein/REAXYS Number 906870

  •  EC Number 238-671-9

  •  MDL number MFCD00008276

  •  PubChem Substance ID 24851275

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Properties

Related Categories Alkynes, Building Blocks, Chemical Synthesis, Internal, Organic Building Blocks More...
Quality Level   100
assay   99%
refractive index   n20/D 1.427 (lit.)
bp   136-137 °C (lit.)
mp   21-24 °C (lit.)
density   0.752 g/mL at 25 °C (lit.)
storage temp.   2-8°C
SMILES string   C[Si](C)(C)C#C[Si](C)(C)C
InChI   1S/C8H18Si2/c1-9(2,3)7-8-10(4,5)6/h1-6H3
InChI key   ZDWYFWIBTZJGOR-UHFFFAOYSA-N

Description

General description

Bis(trimethylsilyl)acetylene (BTMSA) participates as nucleophile in Friedel-Crafts type acylations and alkylations. BTMSA undergoes rhodium catalyzed addition reaction with diarylacetylenes. It undergoes cycloaddition with 1,5-hexadiynes in the presence of CpCo(CO)2 (Cp=cyclopentadienyl) to form benzocyclobutenes. Structure of BTMSA was characterized by a centre of inversion present on triple bond (length=1.208(3)Å). TiCl4-Et2AlCl catalyzed Diels-Alder reaction of BTMSA with norbornadiene has been reported.

Application

Bis(trimethylsilyl)acetylene (BTMSA) was used as starting reagent in the synthesis of functionalized 4-R-1,2-bis(trimethylsilyl)benzenes. It was also used in the synthesis of (+)-brasilenyne and (β-diketanato)Ag(BTMSA).

Packaging

10, 50 g in glass bottle

Safety & Documentation

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UN 1993BF 3 / PGII
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Protocols & Articles

Articles

Diels–Alder Reaction

The Diels–Alder reaction is the reaction between a conjugated diene and an alkene (dienophile) to form unsaturated six-membered rings. Since the reaction involves the formation of a cyclic product vi...
Keywords: Addition reactions, Asymmetric synthesis, Building blocks, Catalysis, Cycloadditions, Diels-Alder reaction, Immobilization

Reagents for C–C Bond Formation

We carry a large variety of electrophiles and nucleophiles that are widely used in C–C bond-forming reactions. This group of products contains many organometallic reagents as well as commonly-used al...
ChemFiles Volume 1 Article 3
Keywords: Acylations, Alkylations

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Peer-Reviewed Papers
15

References

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