Dibutylmagnesium
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| Names | |
|---|---|
| Other names Di-n-butylmagnesium | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider | |
| ECHA InfoCard | 100.013.397 |
| EC Number |
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PubChem CID | |
CompTox Dashboard (EPA) | |
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| Properties | |
| (CH3CH2CH2CH2)2Mg | |
| Molar mass | 138.537 g·mol−1 |
| Appearance | Waxy white solid |
| Density | 0.713 g/mL at 25°C |
| Reacts with water | |
| Hazards | |
| GHS labelling: | |
     | |
| Danger | |
| H250, H260, H314 | |
| P210, P222, P223, P231+P232, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, P370+P378, P402+P404, P405, P422, P501 | |
| Related compounds | |
Related compounds | Dimethylmagnesium |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references | |
Dibutylmagnesium is an organometallic chemical compound of magnesium. Its chemical formula is (CH3CH2CH2CH2)2Mg.[1] Dibutylmagnesium is a chemical compound from the group of organomagnesium compounds. The pure substance is a waxy solid. Commercially, it is marketed as a solution in heptane.[2]
Synthesis
Dibutylmagnesium can be obtained by the reaction of butyllithium with butylmagnesium chloride and the subsequent addition of magnesium 2-ethylhexanoate.[3] The compound can also be prepared by hydrogenation of magnesium, followed by a reaction with 1-butene.[1] It is also possible to prepare dibutylmagnesium using 2-chlorobutane, magnesium powder, and n-butyllithium.[4]
Use
Dibutylmagnesium is used as a convenient reagent for the preparation of organomagnesium compounds.[3][2][5]
References
- ^ a b Sigma-Aldrich Co., Di-n-butylmagnesium solution, 1 M in ether and hexanes. Retrieved on 2018-10-28.
- ^ a b Terry L. Rathman: "Dibutylmagnesium". In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063
- ^ a b Alan W. Duff, Peter B. Hitchcock, et al: "'Dibutylmagnesium', a convenient reagent for the synthesis of useful organic magnesium reagents MgA2 including cyclopentadienyls, aryloxides, and amides. Preparation of Zr(C5H5)Cl3. X-ray structure of [{μ-N(SiMe)3C6H4N}(SiMe3)-o(OEt2)]2." In: Journal of Organometallic Chemistry. Issue 293 (1985), p. 271, doi:10.1016/0022-328X(85)80298-9.
- ^ "Method for preparing dibutylmagnesium" (Patent CN101362772A), retrieved via Google Patents 28 October 2018.
- ^ Michael J. Michalczyk: "Synthesis of magnesium hydride by the reaction of phenylsilane and dibutylmagnesium." In: Organometallics. Issue 11 (1992), p. 2307, doi:10.1021/om00042a055.