187437

Bis(trimethylsilyl)acetylene

99%

• Synonym(s): BTMSA
• Linear Formula: (CH₃)₃SiC≡CSi(CH₃)₃
• CAS Number: 14630-40-1
• Molecular Weight: 170.40
• Beilstein: 906870
• EC Number: 238-671-9
• MDL number: MFCD00008276
• UNSPSC Code: 12352100
• PubChem Substance ID: 24851275
• NACRES: NA.22

Properties

• 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).

Safety Information

• Pictograms: GHS02,GHS07
• Signal Word: Danger
• Hazard Statements: H225,H315,H319,H335
• Precautionary Statements: P210 - P233 - P240 - P241 - P303 + P361 + P353 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 2 - Skin Irrit. 2 - STOT SE 3
• Target Organs: Respiratory system
• Storage Class Code: 3 - Flammable liquids
• WGK: WGK 3
• Flash Point(F): 35.6 °F - closed cup
• Flash Point(C): 2 °C - closed cup
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves