89343-06-6

Basic information

• Product Name: (TRIISOPROPYLSILYL)ACETYLENE
• Synonyms: ETHYNYLTRIISOPROPYLSILANE;(TRIISOPROPYLSILYL)ACETYLENE;(Triisopropylsilyl)acetylene,97%;(Triisopropylsilyl)Acetylene 98+%;(Triisopropylsilyl)acetylene,Ethynyltriisopropylsilane;(TRIISOPROPYLSILYL)ACETYLENE 97%;Triiopropyl silyl acetylene;[Tris(isopropyl)silyl]acetylene
• CAS NO: 89343-06-6
• Molecular Formula: C₁₁H₂₂Si
• Molecular Weight: 182.38
• EINECS: 1312995-182-4
• Product Categories: Acetylenes;Ethynylsilanes;Functionalized Acetylenes;Si (Classes of Silicon Compounds);Si-(C)4 Compounds
• Mol File: 89343-06-6.mol
• Article Data: 8

Chemical Properties

• Melting Point: 50-51 °C
• Boiling Point: 50-52 °C0.6 mm Hg(lit.)
• Flash Point: 133 °F
• Appearance: clear colorless liquid
• Density: 0.813 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.0981mmHg at 25°C
• Refractive Index: n20/D 1.4527(lit.)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Miscible with organic solvents.
• BRN: 3536241
• CAS DataBase Reference: (TRIISOPROPYLSILYL)ACETYLENE(CAS DataBase Reference)
• NIST Chemistry Reference: (TRIISOPROPYLSILYL)ACETYLENE(89343-06-6)
• EPA Substance Registry System: (TRIISOPROPYLSILYL)ACETYLENE(89343-06-6)

Safety Data

• Hazard Codes: Xi
• 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
• Hazardous Substances Data: 89343-06-6(Hazardous Substances Data)

Usage

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

Different sources of media describe the Uses of 89343-06-6 differently. You can refer to the following data:
1. (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.
2. (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.

InChI:InChI=1/C11H22Si/c1-8-12(9(2)3,10(4)5)11(6)7/h1,9-11H,2-7H3

Upstream product

• 1174908-08-7 propargyl alcohol 
• 4131-50-4 tris(1-methylethyl)(phenylethynyl)silane 
• 13154-24-0 triisopropylsilyl chloride 
• 74-86-2 acetylene 
• 74-96-4 ethyl bromide 
• 136449-68-8 4-{Dimethyl-[(triisopropylsilanyl)-ethynyl]-silanyl}-biphenyl 

Downstream Products

• 176977-34-7 ((4-((trimethylsilyl)ethynyl)phenyl)-ethynyl)triisopropylsilane 
• 186772-45-2 1-t-butyl-3-[(triisopropylsilyl)ethynyl]-5-[(trimethylsilyl)ethynyl]benzene 
• 186772-46-3 ethyl 3-[(trimethylsilyl)ethynyl]-5-[(triisopropylsilyl)ethynyl]benzoate 
• 350230-73-8 2,5-bis(octyloxy)-4-[(triisopropylsilyl)ethynyl]benzaldehyde 
• 347399-61-5 N,N-diethyl-N'-[2,6-bis(triisopropylsilylethynyl)-4-tert-butylphenyl]triazene 
• 373596-55-5 4-{4-[(11-{4-[2-(Triisopropylsilyl)ethynyl]phenoxy}undecyl)oxy]phenyl}benzonitrile 
• 448895-62-3 2,2'-bis-(triisopropylsilyl)ethynyltolan 
• 373596-08-8 6,13-bis[(triisopropylsilyl)ethynyl]pentacene 
• 1007374-17-5 1-triisopropylsilyl-2-(dimethylphenylsilyl)ethyne 

Relevant articles and documents

Rhodium(I)-Catalyzed Sequential C(sp)-C(sp3) and C(sp3)-C(sp3) Bond Formation through Migratory Carbene Insertion

A RhI-catalyzed three-component reaction of tert-propargyl alcohol, diazoester, and alkyl halide has been developed. This reaction can be considered as a carbene-involving sequential alkyl and alkynyl coupling, in which C(sp)-C(sp3) and C(sp3)-C(sp3) bonds are built successively on the carbenic carbon atom. The RhI-carbene migratory insertion of an alkynyl moiety and subsequent alkylation are proposed to account for the two separate C-C bond formations. This reaction provides an efficient and tunable method for the construction of all-carbon quaternary center.

Synthesis and characterization of fluorinated heterofluorenecontaining donor-acceptor systems

Chemical Equation Presented A series of oligothiophene- perfluoro-9-heterofluorene donor-acceptor (DA) compounds was synthesized via a combination of nucleophilic aromatic substitution (SNArF) and palladium coupling reactions. These compounds are of interest as possible building blocks for materials with useful electron transport properties, since they possess relatively low LUMO energy levels of-3.3 to -3.6 eV (as determined by differential pulse voltammetry). The HOMO-LUMO energy gaps, as determined by UV-vis spectroscopy, range between 2.4 and 2.5 eV, and photoluminescence emission spectra reveal λems values in the range of 480-600 nm (corresponding to yellow-orange emission). Dilute solution-state photoluminescence quantum yields were significantly lower than those of the pure acceptor heterofluorenes (0.02-0.38 for the DA compounds vs ～1 for the pure acceptors), and notable solvatochromism in the fluorescence suggests emission from a charge-separated state. Theoretical calculations show that HOMO-level electron density is more localized on the thiophene fragment, while the LUMO level electron density is mostly associated with the electron-deficient portion of the molecule. Photovoltaic (PV) devices based on DA/poly-3-hexylthiophene (P3HT) blends exhibit improved performance over P3HT-only devices, suggesting the ability of these DA compounds to transport electrons in the solid state.

Novel reactions of steric encumbered 1,4-dilithio-1,3-butadiene with group 14 electrophiles: Formation and structure of stable dihydroxygermole

Reactions of 1,4-dilithio-1,3-butadiene 1 having bulky silyl ligands at the 1,4-positions with group 14 electrophiles were examined. Reactions of 1,4-dilithio-1,3-butadiene 1 with tetraethoxygermane gave diethoxygermole 5, which was hydrolyzed to give sta