ethenyltrimethylsilane

• ChemBase ID: 137326
• Molecular Formular: C5H12Si
• Molecular Mass: 100.23428
• Monoisotopic Mass: 100.07082692
• SMILES: C[Si](C)(C)C=C
• Canonical SMILES: C=C[Si](C)(C)C
• InChI: InChI=1S/C5H12Si/c1-5-6(2,3)4/h5H,1H2,2-4H3
• InChIKey: GCSJLQSCSDMKTP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethenyltrimethylsilane
• IUPAC Traditional name: silane, ethenyltrimethyl-
• Synonyms: (Trimethylsilyl)ethylene; Ethenyltrimethylsilane; Trimethyl(vinyl)silane; Vinyltrimethylsilane; Trimethyl(vinyl)silane; Trimethylvinylsilane; ethenyltrimethylsilane; 三甲基乙烯基硅烷; 三甲基硅乙烯; 乙烯基三甲基硅; 乙烯基三甲基硅烷; 三甲基乙烯基硅烷

Database IDs

• CAS Number: 754-05-2
• EC Number: 212-042-9
• MDL Number: MFCD00008606
• Beilstein Number: 956572
• PubChem SID: 24884541; 24852813; 162231589
• PubChem CID: 79102

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.5601
• LogD (pH = 7.4): 2.5601
• Log P: 2.5601
• Molar Refractivity: 26.1296 cm^3
• Polarizability: 12.652486 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: -132°C
• Boiling Point: 54-56°C; 55 °C(lit.)
• Flash Point: -11.2 °F; -24 °C; -24°C(-11°F)
• Density: 0.684 g/mL at 25 °C(lit.); 0.690
• Refractive Index: 1.3910; n20/D 1.391; n20/D 1.391(lit.)
• Vapor Pressure: 4.44 psi ( 20 °C)
• Hydrophobicity(logP): 2.809

Safety Information

• European Hazard Symbols: Flammable (F); Irritant (Xi); Harmful (Xn)
• UN Number: 1993; UN1993
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-22-36/37/38; 11-36/37/38
• Safety Statements: 16-26; 9-16-26-29-33-37
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H302-H315-H319-H335; H225-H315-H319-H335
• GHS Precautionary statements: P210-P261-P305 + P351 + P338; P210-P280G-P243-P305+P351+P338-P403+P233
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US)
• RID/ADR: UN 1993 3/PG 2

Product Information

• Purity: ≥97.0% (GC); ≥99.5%; 95%; 97%; 98+%
• Grade: purum
• Impurities: <3% tetrahydrofuran
• Linear Formula: (CH3)3SiCHCH2

DETAILS

Sigma Aldrich - 213950

Application
Used for the preparation of trimethylsilylethyl sulfoxides which in the presence of fluoride ion generate sulfenate nucleophiles.1
Packaging
5, 25, 100 g in glass bottle

Sigma Aldrich - 661724

Application
Preparation of silyl-ethers by Rh(I) catalysis.1
Packaging
25 g in glass bottle

Sigma Aldrich - 95100

Other Notes
Review 1,2,3,4

REFERENCES

• Useful ethylene equivalent in its reaction with electrophiles. The reactivity is controlled by the ability of the Si atom to stabilize a positive charge on a ?-carbon atom. See Appendix 4.
• Acylation under Friedel-Crafts conditions leads to vinyl ketones. Using ɑ?-unsaturated acyl halides, the products are divinyl ketones, which, under the reaction conditions, undergo the Nazarov cyclization to enones: J. Org. Chem., 45, 1046 (1980):
  
• For reviews of the Nazarov cyclization, see: Synthesis, 429 (1983); Org. React., 45, 159 (1994).
• Coupling with the electrophilic reagent generated from an aryl iodide in the presence of Pd(OAc)₂, triphenylphosphine and base, provides a route to styrenes: Chem. Lett., 1993 (1982).
• Also undergoes regioselective addition reactions with alkyllithiums: J. Chem. Soc., Perkin 1, 1131 (1983), and Grignards: Chem. Ber., 117, 383 (1984), to giveɑ-metallated products.
• For use in a 2-carbon extension of aldehydes to ɑ?-unsaturated aldehydes based on cycloaddition to the nitrone, see N-Methylhydroxylamine hydrochloride, L02202.
• For an extensive review of the reactions of vinyl (and allyl) silanes, see: Org. React., 37, 57 (1989).