(Triisopropylsilyl)Acetylene

• CAS: 89343-06-6
• Catalog Number: ACM89343066
• Category: Alkynes
• Molecular Weight: 182.38 g/mol
• Molecular Formula: C11H22Si
• Synonyms: (Triisopropylsilyl)Acetylene,97%; (Triisopropylsilyl)Acetylene 98+%; (Triisopropylsilyl)Acetylene,Ethynyltriisopropylsilane; (Triisopropylsilyl)Acetylene 97%; Triiopropyl Silyl Acetylene; [Tris(Isopropyl)Silyl]Acetylene; Ethynyl[Tris(1-Methylethyl)]Silane; Ethynyltriisopropylsilane; (Triisopropylsilyl)Acetylene; (Triisopropylsilyl)Acetylene; Ethynyl[Tris(1-Methylethyl)]Silane; Ethynyl[Tris(1-Methylethyl)]Silane; Ethynyltriisopropylsilane
• IUPAC Name: ethynyl-tri(propan-2-yl)silane
• Canonical SMILES: CC(C)[Si](C#C)(C(C)C)C(C)C
• InChI Key: KZGWPHUWNWRTEP-UHFFFAOYSA-N
• Boiling Point: 50-52 °C(0.6 mmHg,lit.)
• Flash Point: 56 °C
• Density: 0.813 g/mL(25 °C,lit.)
• Appearance: Clear colorless liquid
• Application: (Triisopropylsilyl)acetylene serves as a versatile reagent frequently employed in various chemical reactions due to its enhanced stability and higher boiling point compared to trimethylsilylacetylene This makes it particularly useful for rhodium-catalyzed asymmetric alkynylation of αβ-unsaturated ketones and the enantioselective synthesis of β-alkynylated nitroalkanes The monoprotected acetylene's bulkier silyl group allows it to endure a broader range of reaction conditions making it an attractive option in transition metal-catalyzed processes It facilitates numerous C–C bond formations including coupling reactions reactions with electrophiles synthesis of polyynes and cross-additions to alkynes Its applications extend to hydroalkynylation direct alkynylation conjugate and cycloaddition additions as well as ring-opening reactions Additionally the asymmetric addition to unsaturated carbonyl compounds using cobalt/Duphos catalysts and Sonogashira coupling reactions with other compounds further highlight its utility in synthetic chemistry
• Exact Mass: 182.14900
• Hazard Statements: H226 Flammable liquid and vapour.; H315 Causes skin irritation.; H319 Causes serious eye irritation.; H335 May cause respiratory irritation.
• H-Bond Acceptor: 0
• H-Bond Donor: 0
• Packing Group: III
• Precautionary Statements: P261 Avoid breathing dust/fume/gas/mist/vapours/spray.; P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
• RIDADR: NONH for all modes of transport
• Safety Description: S26-S37/39
• Signal Word: Warning
• Symbol: GHS07
• WGK Germany: 3

Custom Q&A

What is the molecular formula of (Triisopropylsilyl)acetylene?

The molecular formula is C11H22Si.

What is the molecular weight of (Triisopropylsilyl)acetylene?

The molecular weight is 182.38 g/mol.

What is the IUPAC name of (Triisopropylsilyl)acetylene?

The IUPAC name is ethynyl-tri(propan-2-yl)silane.

What is the InChI of (Triisopropylsilyl)acetylene?

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

What is the InChIKey of (Triisopropylsilyl)acetylene?

The InChIKey is KZGWPHUWNWRTEP-UHFFFAOYSA-N.

What is the Canonical SMILES of (Triisopropylsilyl)acetylene?

The Canonical SMILES is CC(C)[Si](C#C)(C(C)C).

What is the CAS number of (Triisopropylsilyl)acetylene?

The CAS number is 89343-06-6.

What is the European Community (EC) Number of (Triisopropylsilyl)acetylene?

The European Community (EC) Number is 629-580-9.

What is the UNII of (Triisopropylsilyl)acetylene?

The UNII is DWX24P8A9S.

Does (Triisopropylsilyl)acetylene have a defined atom stereocenter count?

No, (Triisopropylsilyl)acetylene does not have a defined atom stereocenter count.

Synthetic Use

Upstream Synthesis Route 1

• 136449-68-8

• 89343-06-6

Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 31, p. 3787 - 3790

Upstream Synthesis Route 2

• 13154-24-0
• 74-86-2

• 89343-06-6

Reference: [1] Journal of Organic Chemistry, 2002, vol. 67, # 19, p. 6841 - 6844

Downstream Synthesis Route 1

• 873-75-6
• 89343-06-6

• 10602-04-7

Reference: [1] Tetrahedron, 2015, vol. 71, # 35, p. 5965 - 5972

Downstream Synthesis Route 2

• 35578-47-3
• 89343-06-6

• 189619-30-5

Reference: [1]Angewandte Chemie - International Edition in English,1997,vol. 36,p. 631 - 634

Downstream Synthesis Route 3

• 89343-06-6
• 202865-66-5

• 229027-94-5

Reference: [1]Collection of Czechoslovak Chemical Communications,1999,vol. 64,p. 649 - 672

* For details of the synthesis route, please refer to the original source to ensure accuracy.