187437

Bis(trimethylsilyl)acetylene

99%

• Synonym(s): BTMSA
• Linear Formula: (CH₃)₃SiC≡CSi(CH₃)₃
• CAS Number: 14630-40-1
• Molecular Weight: 170.40
• UNSPSC Code: 12352100
• NACRES: NA.22
• PubChem Substance ID: 24851275
• EC Number: 238-671-9
• Beilstein/REAXYS Number: 906870
• MDL number: MFCD00008276
• Assay: 99%

Properties

• Quality Segment: 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.[1] 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[2]. It was also used in the synthesis of (+)-brasilenyne[3] and (β-diketanato)Ag(BTMSA)[3].

Safety Information

• pictograms: GHS02,GHS07
• signalword: Danger
• hcodes: H225,H315,H319,H335
• pcodes: 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: 3 - Flammable liquids
• wgk: WGK 3
• flash_point_f: 35.6 °F - closed cup
• flash_point_c: 2 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter