trimethyl(prop-1-yn-1-yl)silane

• ChemBase ID: 122853
• Molecular Formular: C6H12Si
• Molecular Mass: 112.24498
• Monoisotopic Mass: 112.07082692
• SMILES: C(#CC)[Si](C)(C)C
• Canonical SMILES: CC#C[Si](C)(C)C
• InChI: InChI=1S/C6H12Si/c1-5-6-7(2,3)4/h1-4H3
• InChIKey: DCGLONGLPGISNX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethyl(prop-1-yn-1-yl)silane
• IUPAC Traditional name: trimethyl(prop-1-yn-1-yl)silane
• Synonyms: Trimethyl-1-propynylsilane; 1-(Trimethylsilyl)propyne; trimethyl(prop-1-yn-1-yl)silane; Methyl trimethylsilyl acetylene; Propargyltrimethylsilane; 1-Trimethylsilyl-1-propyne; 1-(Trimethylsilyl)-1-propyne; Trimethyl-1-propyn-1-ylsilane; 1-(Trimethylsilyl)-1-propyne; 1-Methyl-2-trimethylsilylacetylene; 1-Propynyltrimethylsilane; Methyl(trimethylsilyl)acetylene; Methyl(trimethylsilyl)ethyne; T 3728; Trimethyl(1-propyn-1-yl)silane; 1-(Trimethylsilyl)propyne; 三甲基-1-丙炔基硅烷; 1-(三甲基硅基)丙炔; 1-三甲基甲硅烷基-1-丙炔

Database IDs

• CAS Number: 6224-91-5
• EC Number: 228-314-5
• MDL Number: MFCD00009271
• Beilstein Number: 1071311
• PubChem SID: 24889721; 24854680; 162217206
• PubChem CID: 80363

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.8286
• LogD (pH = 7.4): 2.8286
• Log P: 2.8286
• Molar Refractivity: 29.1311 cm^3
• Polarizability: 13.626703 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -69°C
• Boiling Point: 99-100 °C(lit.); 99-100°C
• Flash Point: -3°C(26°F); 39.2 °F; 4 °C
• Density: 0.753; 0.758 g/mL at 25 °C(lit.)
• Refractive Index: 1.4200; n20/D 1.417; n20/D 1.417(lit.)
• Vapor Density: >1 (vs air)
• Hydrophobicity(logP): 2.264

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11; 11-36/37/38
• Safety Statements: 16-26-36; 9-16-29-33
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H225-H315-H319-H335
• GHS Precautionary statements: P210-P243-P403; P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (GC); 95%; 97%; 98%; 99%
• Grade: purum
• Linear Formula: CH3C≡CSi(CH3)3

DETAILS

Sigma Aldrich - 244481

Packaging
5, 25 g in glass bottle
Application
Reagent for the conversion of aldehydes to 1,3-dienes in the presence of Cp2Zr(H)CI.1 Polymerization catalyzed by tantalum pentachloride/triphenylbismuth2 yields polymers with high oxygen permeability.3
Used in a synthesis of highly substituted indenes via palladium-catalyzed carboannulation. Synthesis of indenones via a rhodium-catalyzed reaction with 2-bromophenylboronic acids.

Sigma Aldrich - 92767

Other Notes
Important building block for synthesizing alkynes, 1,5-dienes, 1,5-enynes and 1,5-diynes via its lithium or copper derivative1,2,3; Synthesis of α-allenic alcohols and amines4,5

Toronto Research Chemicals - T796890

1-(Trimethylsilyl)propyne is used in the synthesis of alkynyl silane derivative.

REFERENCES

• Falck, J., et al.: Bioorg. Med. Chem. Lett., 14, 4987 (2004)
• Zlotos, D., et al.: J. Med. Chem., 47, 3561 (2004)
• Alkylation of the lithio-derivative proceeds with only a small amount of allylic rearrangement to the allene, and is thus a useful route to substituted terminal alkynes: Tetrahedron Lett., 5041 (1968):