trimethyl(prop-2-en-1-yl)silane

• ChemBase ID: 107361
• Molecular Formular: C6H14Si
• Molecular Mass: 114.26086
• Monoisotopic Mass: 114.08647698
• SMILES: C[Si](C)(C)CC=C
• Canonical SMILES: C=CC[Si](C)(C)C
• InChI: InChI=1S/C6H14Si/c1-5-6-7(2,3)4/h5H,1,6H2,2-4H3
• InChIKey: HYWCXWRMUZYRPH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: trimethyl(prop-2-en-1-yl)silane
• IUPAC Traditional name: silane, trimethyl-2-propenyl-
• Synonyms: ALLYL TRIMETHYLSILANE; 3-(Trimethylsilyl)propene; Allyltrimethylsilane; Allyltrimethylsilane; 3-(三甲基甲硅烷基)丙烯; 烯丙基三甲基硅烷

Database IDs

• CAS Number: 762-72-1
• EC Number: 212-104-5
• MDL Number: MFCD00008635
• Beilstein Number: 906755
• PubChem SID: 162093901; 24852502
• PubChem CID: 69808

CALCULATED PROPERTIES

• H Acceptors: 0
• H Donor: 0
• LogD (pH = 5.5): 2.9051
• LogD (pH = 7.4): 2.9051
• Log P: 2.9051
• Molar Refractivity: 31.4083 cm^3
• Polarizability: 14.499341 Å^3
• Polar Surface Area: 0.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 84-88 °C(lit.); 85-86°C
• Flash Point: -10°C(14°F); 16 °C; 60.8 °F
• Density: 0.717; 0.719 g/mL at 25 °C(lit.)
• Refractive Index: 1.4080; n20/D 1.407(lit.)

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: 11-36/37/38; R:36/37/38
• Safety Statements: 16-26-36; 9-16-23-26-33-37; S:20-25-26-37/39
• TSCA Listed: 是
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H315-H319-H335
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P405-P501A; 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%; 98%; 98+%
• Linear Formula: H2C=CHCH2Si(CH3)3

DETAILS

MP Biomedicals - 05203439

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 208264

Packaging
10, 50 g in glass bottle

REFERENCES

• Reactions with electrophiles illustrate the ?-effect (see Appendix 4); e.g. acid chlorides with a Lewis acid give allyl ketones: J. Organomet. Chem., 85, 149 (1975):
  
• Similarly, carbonyl compounds are converted to homoallylic alcohols: J. Organomet. Chem., 69, C15 (1974). In the TiCl₄ promoted reaction with enones, behaves as an allyl anion equivalent, giving the product of conjugate addition (Hosomi-Sakurai reaction): J. Am. Chem. Soc., 99, 1673 (1977);105, 2354 (1983); Org. Synth. Coll., 7, 443 (1990):
  
• More recent studies have shown that TMS cyclopentanes are also formed in these reactions via a competing [3+2] cycloaddition mechanism: Tetrahedron, 49, 9955 (1993). Chemoselective addition to aldehydes can be accomplished in the presence of a ketone, using Scandium(III) trifluoromethanesulfonate hydrate, 40566 as catalyst: Synthesis, 1822 (1998).
• In the presence of F^-, functions as an allyl anion equivalent, affording homoallylic alcohols from carbonyl compounds: Tetrahedron Lett., 3043 (1978), and adding to a variety of Michael acceptors: Tetrahedron Lett., 25, 3213 (1984); J. Org. Chem., 51, 1745 (1986). For a review of reactivity in the presence of Lewis acids and F^-, see: J. Prakt. Chem./ Chem. Ztg., 336, 375 (1994).
• Has also been used, in the presence of a catalyst such as p-TsOH, I₂, Br₂ or TfOH, as a silylating agent for alcohols, phenols and carboxylic acids: Tetrahedron Lett., 21, 835 (1980); J. Org. Chem., 46, 5212 (1981). The advantage over more conventional silylation methods is that the only by-product is the neutral gas propene.