| Identification | Back Directory | [Name]
(2-BROMOALLYL)TRIMETHYLSILANE | [CAS]
81790-10-5 | [Synonyms]
(2-BROMOALLY)TRIMETHYLSILANE
(2-BROMOALLYL)TRIMETHYLSILANE
2-BROMO-3-(TRIMETHYLSILYL)PROPENE
(2-Bromoallyl)trimethylsilane >
2-Bromo-3-trimethylsilyl-1-propene
Silane,(2-bromo-2-propen-1-yl)trimethyl-
(2-Bromo-2-propen-1-yl)(trimethyl)silane
(2-BROMOALLYL)TRIMETHYLSILANE, TECH., 90 % | [Molecular Formula]
C6H13BrSi | [MDL Number]
MFCD00043054 | [MOL File]
81790-10-5.mol | [Molecular Weight]
193.16 |
| Chemical Properties | Back Directory | [Boiling point ]
82-85 °C60 mm Hg(lit.)
| [density ]
1.121 g/mL at 25 °C(lit.)
| [refractive index ]
n20/D 1.462(lit.)
| [Fp ]
87 °F
| [storage temp. ]
2-8°C
| [solubility ]
sol alcohol, acetone, ether, THF, pentane; insol water. | [form ]
liquid | [BRN ]
3600686 |
| Hazard Information | Back Directory | [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). | [Preparation]
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.] |
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Energy Chemical
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021-021-58432009 400-005-6266 |
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http://www.energy-chemical.com |
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