| (2-BROMOALLYL)TRIMETHYLSILANE Basic information |
| Product Name: | (2-BROMOALLYL)TRIMETHYLSILANE |
| Synonyms: | (2-BROMOALLYL)TRIMETHYLSILANE;(2-BROMOALLY)TRIMETHYLSILANE;2-BROMO-3-(TRIMETHYLSILYL)PROPENE;(2-BROMOALLYL)TRIMETHYLSILANE, TECH., 90 %; (2-Bromo-2-propen-1-yl)(trimethyl)silane;Silane,(2-bromo-2-propen-1-yl)trimethyl-;2-Bromo-3-trimethylsilyl-1-propene;(2-Bromoallyl)trimethylsilane > |
| CAS: | 81790-10-5 |
| MF: | C6H13BrSi |
| MW: | 193.16 |
| EINECS: | |
| Product Categories: | Si (Classes of Silicon Compounds);Si-(C)4 Compounds;Silicon Compounds (for Synthesis);Synthetic Organic Chemistry;Vinylsilanes, Allylsilanes;Chemical Synthesis;Organometallic Reagents;Organosilicon;Others |
| Mol File: | 81790-10-5.mol |
| (2-BROMOALLYL)TRIMETHYLSILANE Chemical Properties |
| Boiling point | 82-85 °C/60 mmHg (lit.) |
| density | 1.121 g/mL at 25 °C (lit.) |
| refractive index | n |
| Fp | 87 °F |
| storage temp. | 2-8°C |
| solubility | sol alcohol, acetone, ether, THF, pentane; insol water. |
| BRN | 3600686 |
| Safety Information |
| Hazard Codes | Xi |
| Risk Statements | 10-36/37/38 |
| Safety Statements | 16-26-36 |
| RIDADR | UN 1993 3/PG 3 |
| WGK Germany | 3 |
| F | 8-10 |
| HazardClass | 3.2 |
| PackingGroup | III |
| MSDS Information |
| Provider | Language |
|---|---|
| SigmaAldrich | English |
| (2-BROMOALLYL)TRIMETHYLSILANE Usage And Synthesis |
| 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.] |
| (2-BROMOALLYL)TRIMETHYLSILANE Preparation Products And Raw materials |
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