Dibutylmagnesium: Difference between revisions
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'''Dibutylmagnesium''' is an [[organometallic]] chemical compound of [[magnesium]]. Its chemical formula is {{chem|C|8|H|18|Mg}}.<ref |
'''Dibutylmagnesium''' is an [[organometallic]] chemical compound of [[magnesium]]. Its chemical formula is {{chem|C|8|H|18|Mg}}.<ref name=Sigma /> Dibutylmagnesium is a chemical compound from the group of [[organomagnesium compound]]s. The pure substance is a waxy solid. Commercially, it is marketed as solution in [[heptane]].<ref name=Encyc /> |
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==Synthesis== |
==Synthesis== |
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Dibutylmagnesium can be obtained by reaction of [[butyllithium]] with magnesium butylchloride and subsequent addition of magnesium 2-ethylhexanoate.<ref name= |
Dibutylmagnesium can be obtained by reaction of [[butyllithium]] with magnesium butylchloride and subsequent addition of magnesium 2-ethylhexanoate.<ref name=Orig /> The compound can also be prepared by hydrogenation of magnesium, followed by reaction with [[1-butene]].<ref name="Sigma" /> It is also possible to prepare dibutylmagnesium using [[2-chlorobutane]], magnesium powder, and [[n-butyllithium]].<ref name=Patent /> |
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==Use== |
==Use== |
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Dibutylmagnesium is used as a convenient reagent for the preparation of [[organomagnesium compound]]s.<ref name=Orig /><ref name=Encyc /><ref name=TransMet /> |
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==References== |
==References== |
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<references> |
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{{Reflist}} |
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<ref name=Encyc>Terry L. Rathman: "Dibutylmagnesium". In: ''[[Encyclopedia of Reagents for Organic Synthesis]]'', 2001, [[doi:10.1002/047084289X.rd063]]</ref> |
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| ⚫ | <ref name=Orig>Alan W. Duff, Peter B. Hitchcock, ''et al'': "'Dibutylmagnesium', a convenient reagent for the synthesis of useful organic magnesium reagents MgA<sub>2</sub> including cyclopentadienyls, aryloxides, and amides. Preparation of Zr(C<sub>5</sub>H<sub>5</sub>)Cl<sub>3</sub>. X-ray structure of [{μ-N(SiMe)<sub>3</sub>C<sub>6</sub>H<sub>4</sub>N}(SiMe<sub>3</sub>)-o(OEt<sub>2</sub>)]<sub>2</sub>." In: ''[[Journal of Organometallic Chemistry]].'' Issue 293 (1985), p. 271, {{doi|10.1016/0022-328X(85)80298-9}}.</ref> |
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<ref name=Patent>"[https://patents.google.com/patent/CN101362772A/en Method for preparing dibutylmagnesium]" (Patent CN101362772A), retrieved via [[Google Patents]] 28 October 2018.</ref> |
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<ref name=Sigma>{{Sigma-Aldrich|id=731110|name=Di-n-butylmagnesium solution, 1 M in ether and hexanes|accessdate=2018-10-28}}</ref> |
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<ref name=TransMet>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}}.</ref> |
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</references> |
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[[Category:Magnesium compounds]] |
[[Category:Magnesium compounds]] |
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[[Category:Organomagnesium compounds]] |
[[Category:Organomagnesium compounds]] |
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[[Category:Butyl compounds]] |
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[[Category:Pyrophoric materials]] |
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Latest revision as of 06:37, 10 June 2024
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| Names | |
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| Other names
Di-n-butylmagnesium
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| Identifiers | |
3D model (JSmol)
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| ChemSpider | |
| ECHA InfoCard | 100.013.397 |
| EC Number |
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PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C 8H 18Mg | |
| Molar mass | 138.53 |
| Appearance | Waxy solid |
| Density | 0.713 g/mL at 25°C |
| Hazards | |
| GHS labelling: | |
    
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| 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
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Dimethylmagnesium |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Dibutylmagnesium is an organometallic chemical compound of magnesium. Its chemical formula is C
8H
18Mg.[1] Dibutylmagnesium is a chemical compound from the group of organomagnesium compounds. The pure substance is a waxy solid. Commercially, it is marketed as solution in heptane.[2]
Synthesis
[edit]Dibutylmagnesium can be obtained by reaction of butyllithium with magnesium butylchloride and subsequent addition of magnesium 2-ethylhexanoate.[3] The compound can also be prepared by hydrogenation of magnesium, followed by reaction with 1-butene.[1] It is also possible to prepare dibutylmagnesium using 2-chlorobutane, magnesium powder, and n-butyllithium.[4]
Use
[edit]Dibutylmagnesium is used as a convenient reagent for the preparation of organomagnesium compounds.[3][2][5]
References
[edit]- ^ 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.