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Dibutylmagnesium

From Wikipedia, the free encyclopedia
Dibutylmagnesium
Names
Other names
Di-n-butylmagnesium
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.013.397 Edit this at Wikidata
EC Number
  • 214-736-7
  • InChI=1S/2C4H9.Mg/c2*1-3-4-2;/h2*1,3-4H2,2H3;/q2*-1;+2
    Key: KJJBSBKRXUVBMX-UHFFFAOYSA-N
  • CCC[CH2-].CCC[CH2-].[Mg+2]
Properties
C
8
H
18
Mg
Molar mass 138.53
Appearance Waxy solid
Density 0.713 g/mL at 25°C
Hazards
GHS labelling:
GHS02: Flammable GHS05: Corrosive GHS07: Exclamation mark GHS08: Health hazard GHS09: Environmental hazard
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).

Dibutylmagnesium is an organometallic chemical compound of magnesium. Its chemical formula is C
8
H
18
Mg
.[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]
  1. ^ a b Sigma-Aldrich Co., Di-n-butylmagnesium solution, 1 M in ether and hexanes. Retrieved on 2018-10-28.
  2. ^ a b Terry L. Rathman: "Dibutylmagnesium". In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063
  3. ^ 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.
  4. ^ "Method for preparing dibutylmagnesium" (Patent CN101362772A), retrieved via Google Patents 28 October 2018.
  5. ^ 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.