ethynyltrimethylsilane

• ChemBase ID: 8579
• Molecular Formular: C5H10Si
• Molecular Mass: 98.2184
• Monoisotopic Mass: 98.05517685
• SMILES: C[Si](C)(C)C#C
• Canonical SMILES: C#C[Si](C)(C)C
• InChI: InChI=1S/C5H10Si/c1-5-6(2,3)4/h1H,2-4H3
• InChIKey: CWMFRHBXRUITQE-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethynyltrimethylsilane
• IUPAC Traditional name: trimethylsilylacetylene
• Synonyms: Trimethylsilylacetylene; Ethynyltrimethylsilane; (Trimethylsilyl)acetylene; TMS acetylene; (Trimethylsilyl)acetylene; EthynyltriMethylsilane; Ethynyltrimethylsilane; TRIMETHYLSILYLACETYLENE; 三甲基硅乙炔; 乙炔基三甲基硅烷; (三甲基硅烷基)乙炔

Database IDs

• CAS Number: 1066-54-2
• EC Number: 213-919-9
• MDL Number: MFCD00008569
• Beilstein Number: 906752
• PubChem SID: 24845295; 160971886; 24853048
• PubChem CID: 66111
• Chemspider ID: 59499
• Wikipedia Title: Trimethylsilylacetylene

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.2404
• LogD (pH = 7.4): 2.2404
• Log P: 2.2404
• Molar Refractivity: 23.6303 cm^3
• Polarizability: 11.780916 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: colorless liquid
• Boiling Point: 52-53°C; 52-53°C; 53 °C(lit.); 53°C
• Flash Point: <-34°C(-29°F); -26°C; -29.2 °F; -34 °C
• Density: 0.69 g/mL; 0.695 g/mL at 25 °C(lit.); 0.709; 0.710
• Refractive Index: 1.3900; 1.3990; n20/D 1.388(lit.)
• Vapor Pressure: 4.18 psi ( 20 °C)

Safety Information

• Storage Warning: Highly Flammable/Irritant/Keep Cold; IRRITANT, KEEP COLD, FLAMMABLE
• 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; R:36/37/38; R11
• Safety Statements: 16-26; 9-16-29-33; S:20-25-26-37/39; S16 S24/25 S29 S33 S9
• TSCA Listed: false; 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225; H225-H315-H319-H335
• GHS Precautionary statements: P210-P241-P280-P303+P361+P353-P403+P235-P501A; P210-P261-P305 + P351 + P338
• Personal Protective Equipment: Faceshields, full-face respirator (US), Gloves, Goggles, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (GC); 97%; 98%
• Grade: purum
• Linear Formula: (CH3)3SiC≡CH

DETAILS

MP Biomedicals - 05206015

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 218170

Application
Pyrazole syntheses via 1,3-Dipolar cycloaddition of diazo compounds to acetylenes.1
Substrate for nickel-catalyzed cross-coupling with benzonitriles.
Packaging
1, 5, 25 g in ampule
100 g in glass bottle

Sigma Aldrich - 02470

Other Notes
Reagent for ethynylations, review1,2,3

REFERENCES

• Pd catalyzed coupling with aryl bromides or iodides gives aryl TMS alkynes, from which the TMS group is readily cleaved by K₂CO₃ in MeOH: Synthesis, 627 (1980); J. Org. Chem., 46, 2280 (1981). Coupling with 1-bromo-2-nitrobenzene or ethyl 2-bromocarbanilate gives indole precursors. Other terminal alkynes lead to 2-substituted indoles: Heterocycles, 24, 31 (1986):
  
• Cross-coupling with aryl halides can also be catalyzed by Pd-C in the presence of Ph₃P, CuI and Et₃N: Synth. Commun., 20, 2059 (1990); for an example, see 2-Bromonaphthalene, A15300. Pd catalyzed coupling with quinolinol and isoquinolinol triflates has also been reported: Tetrahedron, 51, 3737 (1995). For coupling with vinyl halides catalyzed by Tetrakis(triphenylphosphine)palladium(0), 10548 in the presence of CuI as an example of a route to enynes, see: Tetrahedron Lett., 30, 6997 (1989); Org. Synth. Coll., 9, 117 (1998). CuCl-TMEDA catalyzed oxidative (Hay) coupling gives bis(TMS)-1,3-butadiyne: Org. Synth. Coll., 8, 63 (1993).
• For the synthesis of iodoalkenes by radical addition of perfluoroalkyl iodides, see: J. Org. Chem., 47, 2251 (1982).