399264

(tert-Butyldimethylsilyl)acetylene

99%

• Synonym(s): Ethynyl-tert-butyldimethylsilane
• Linear Formula: (CH₃)₃CSi(CH₃)₂C≡CH
• CAS Number: 86318-61-8
• Molecular Weight: 140.30
• Beilstein/REAXYS Number: 1921466
• MDL number: MFCD00191877
• UNSPSC Code: 12352100
• PubChem Substance ID: 24864798
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 99%
• refractive index: n20/D 1.451 (lit.)
• bp: 116-117 °C (lit.)
• density: 0.751 g/mL at 25 °C (lit.)
• SMILES string: CC(C)(C)[Si](C)(C)C#C
• InChI: 1S/C8H16Si/c1-7-9(5,6)8(2,3)4/h1H,2-6H3
• InChI key: RTYNRTUKJVYEIE-UHFFFAOYSA-N

Description

General description

(tert-Butyldimethylsilyl)acetylene is a bulky trialkylsilyl-protected alkyne. It participates in Cadiot-Chodkiewicz cross-coupling reaction with various bromoalkynes to afford synthetically useful unsymmetrical diynes.

(tert-Butyldimethylsilyl)acetylene readily undergoes cross-dimerization reaction with various internal phenyl acetylenes in the presence of rhodium dimers and bidentate phosphine ligands to afford enynes.

Application

(tert-Butyldimethylsilyl)acetylene may be used in the synthesis of β-alkynylketone and β-alkynyl aldehydes.

Safety Information

• pictograms: GHS02
• signalword: Danger
• hcodes: H225
• pcodes: P210
• Hazard Classifications: Flam. Liq. 2
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 42.8 °F - closed cup
• flash_point_c: 6 °C - closed cup
• ppe: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter