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(2-?????)??????
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(2-?????)?????? ??
- ?? ?
- 82-85 °C/60 mmHg (lit.)
- ??
- 1.121 g/mL at 25 °C (lit.)
- ???
- n
20/D 1.462(lit.)
- ???
- 87 °F
- ?? ??
- 2-8°C
- ???
- ???, ???, ???, ?????????, ??? ???? ?? ??????.
- ??? ??
- liquid
- BRN
- 3600686
- InChI
- 1S/C6H13BrSi/c1-6(7)5-8(2,3)4/h1,5H2,2-4H3
- InChIKey
- LUPQCAARZVEFMT-UHFFFAOYSA-N
- SMILES
- C[Si](C)(C)CC(Br)=C
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- ?? ? ???? ?? (GHS)
| ??? ?? | Xi | ||
|---|---|---|---|
| ?? ???? ?? | 10-36/37/38 | ||
| ????? | 16-26-36 | ||
| ????(UN No.) | UN 1993 3/PG 3 | ||
| WGK ?? | 3 | ||
| F ?????? | 8-10 | ||
| HS ?? | 2931.90.9010 | ||
| ?? ?? | 3.2 | ||
| ???? | III | ||
| ???? ??? | 3 - Flammable liquids | ||
| Hazard Classifications | Eye Irrit. 2 Flam. Liq. 3 Skin Irrit. 2 STOT SE 3 |
(2-?????)?????? C??? ??, ??, ??
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bp 46–50°C/20 mmHg,64–65°C/38– 39 mmHg.??
2-Bromo-3-trimethylsilyl-1-propene can be used as synthon for CH2=CCH2TMS1–3 and CH2=CBrCH2;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=CCH2OH (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).
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reaction of 2,3-dibromopropene with lithium (trimethylsilyl)cuprate in HMPA at 0°C (63–90%);(2) reaction of 2,3-dibromopropene with trichlorosilane in the presence of trichlorosilane and copper( I) chloride, followed by treatment with methylmagnesium bromide (63–71%).Purification Methods
It is fractionally distilled through an efficient column. It is flammable. [Trost & Chan J Am Chem Soc 104 3733 1982, Trost & Coppola J Am Chem Soc 104 6879 1982.](2-?????)?????? ?? ?? ? ???
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