Chemical Property of (2-BROMOALLYL)TRIMETHYLSILANE
Chemical Property:
- Vapor Pressure:6.14mmHg at 25°C
- Refractive Index:n20/D 1.462(lit.)
- Boiling Point:82-85 °C60 mm Hg(lit.)
- Flash Point:87 °F
- PSA：0.00000
- Density:1.121 g/mL at 25 °C(lit.)
- LogP:3.23320
- Storage Temp.:2-8°C
- Solubility.:sol alcohol, acetone, ether, THF, pentane; insol water.
- Hydrogen Bond Donor Count:0
- Hydrogen Bond Acceptor Count:0
- Rotatable Bond Count:2
- Exact Mass:191.99699
- Heavy Atom Count:8
- Complexity:91.2
- Purity/Quality:
-
98%,99%, *data from raw suppliers
(2-Bromoallyl)trimethylsilane *data from reagent suppliers
Safty Information:
- Pictogram(s):
- Hazard Codes:Xi
- Statements:
10-36/37/38
- Safety Statements:
16-26-36
- MSDS Files:
-
SDS file from LookChem
Useful:
- Canonical SMILES:C[Si](C)(C)CC(=C)Br
-
Physical properties
bp 46–50°C/20 mmHg,64–65°C/38–
39 mmHg.
-
Uses
2-Bromo-3-trimethylsilyl-1-propene can be used as synthon for CH2=C?CH2TMS1–3 and CH2=CBrC?H2;2 for
synthesis of 1-trimethylsilylmethyl-substituted 1,3-butadienes.The 1-trimethylsilylmethylvinyl
anion CH2=C(M)CH2TMS (2) (M = Li, Mg, Cu,
etc.), readily prepared from 2-bromo-3-trimethylsilyl-1-propene
(1) under typical conditions, allows the introduction of the
synthetically useful 1-trimethylsilylmethylvinyl group to a wide
variety of substrates. Ring opening of 1-butene oxide with the
Grignard reagent (2) (M = MgBr) in the presence of copper(I)
iodide gives only one regioisomer. Subsequent desilylative oxidation
of this allyl alcohol to α-methylene-γ-lactones provides
further utility of (1) as a 1-hydroxymethylvinyl anion equivalent,
i.e. CH2=?C?CH2OH (eq 1).Alternatively, the alcohol
from trans-2,3-epoxybutane provides a route to the unstable sixmembered
β,γ-unsaturated lactone (eq 2).The copper-catalyzed
1,4-addition to the typically unreactive mesityl oxide proceeds
smoothly. The versatility of the allylsilane moiety is again illustrated
in the ethylaluminum dichloride-induced cyclization of the
adduct to a tertiary cyclopentanol in high yield (eq 3).
