360031

(Triisopropylsilyl)acetylene

97%

• Synonym(s): Ethynyltriisopropylsilane
• Linear Formula: [(CH₃)₂CH]₃SiC≡CH
• CAS Number: 89343-06-6
• Molecular Weight: 182.38
• Beilstein/REAXYS Number: 3536241
• MDL number: MFCD00075452
• UNSPSC Code: 12352100
• PubChem Substance ID: 24862139
• NACRES: NA.22

Properties

• Quality Level: 100
• assay: 97%
• form: liquid
• refractive index: n20/D 1.4527 (lit.)
• bp: 50-52 °C/0.6 mmHg (lit.)
• density: 0.813 g/mL at 25 °C (lit.)
• SMILES string: CC(C)[Si](C#C)(C(C)C)C(C)C
• InChI: 1S/C11H22Si/c1-8-12(9(2)3,10(4)5)11(6)7/h1,9-11H,2-7H3
• InChI key: KZGWPHUWNWRTEP-UHFFFAOYSA-N

Description

General description

Asymmetric addition of (triisopropylsilyl)acetylene to α,β,γ,δ-unsaturated carbonyl compounds in the presence of a cobalt/Duphos catalyst is reported. A Sonogashira coupling reaction between 1-bromo-3-iodo-5-tertbutylbenzene and (triisopropylsilyl)acetylene is reported.

Application

(Triisopropylsilyl)acetylene may be used as reagent for the rhodium-catalyzed asymmetric alkynylation of various α,β-unsaturated ketones. It may be used as reagent in the enantioselective synthesis of β-alkynylated nitroalkanes.

Safety Information

• pictograms: GHS02,GHS07
• signalword: Warning
• hcodes: H226,H315,H319,H335
• pcodes: P210 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: Eye Irrit. 2 - Flam. Liq. 3 - Skin Irrit. 2 - STOT SE 3
• target_organs: Respiratory system
• Storage Class: 3 - Flammable liquids
• wgk_germany: WGK 3
• flash_point_f: 132.8 °F - closed cup
• flash_point_c: 56 °C - closed cup
• ppe: Eyeshields, Gloves, type ABEK (EN14387) respirator filter