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| (TRIISOPROPYLSILYL)ACETYLENE Basic information |
| (TRIISOPROPYLSILYL)ACETYLENE Chemical Properties |
| Melting point | 50-51 °C | | Boiling point | 50-52 °C/0.6 mmHg (lit.) | | density | 0.813 g/mL at 25 °C (lit.) | | refractive index | n20/D 1.4527(lit.) | | Fp | 133 °F | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Miscible with organic solvents. | | Specific Gravity | 0.813 | | Hydrolytic Sensitivity | 4: no reaction with water under neutral conditions | | BRN | 3536241 | | InChIKey | KZGWPHUWNWRTEP-UHFFFAOYSA-N | | CAS DataBase Reference | 89343-06-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36/37/39-37/39 | | RIDADR | UN 1993 3/PG 3 | | WGK Germany | 3 | | TSCA | N | | HazardClass | 3.2 | | PackingGroup | III | | HS Code | 29319090 |
| (TRIISOPROPYLSILYL)ACETYLENE Usage And Synthesis |
| Chemical Properties | clear colorless liquid | | Physical properties | colorless clear liquid; bp 50–52 °C at 0.8 hPa
(0.6 mmHg), flash point 56 °C (closed cup); d = 0.813. | | Uses | (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. | | Uses | (Triisopropylsilyl)acetylene (TIPS-acetylene) is an
easily handled and inexpensive monoprotected acetylene used
as an attractive substitute for trimethylsilylacetylene (TMSacetylene).
The bulkier silyl protecting group of TIPS-acetylene
provides stability in a wider range of reaction conditions than
TMS-acetylene. Its higher boiling point also provides better handling
and safety than TMS-acetylene (bp 87–88°C at 12 hPa
(9 mmHg)). The general utility of TIPS-acetylene is often highlighted
in the transition metal-catalyzed C–C bond formations， including but not limited to transition metal-catalyzed Coupling Reactions；Reaction of TIPS-acetylide with Electrophiles；Synthesis of Polyynes；Transition Metal-catalyzed Cross-addition of TIPSacetylene
to Alkynes；Hydroalkynylation；Direct Alkynylation；Conjugate Addition；Cycloaddition；Ring-opening Reactions etc. | | 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. |
| (TRIISOPROPYLSILYL)ACETYLENE Preparation Products And Raw materials |
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