Dibutylmagnesium

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Dibutylmagnesium
Di-n-butylmagnesium.svg
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
8H
18Mg
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
Signal word
 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 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[]

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.[4] It is also possible to prepare dibutylmagnesium using 2-chlorobutane, magnesium powder, and n-butyllithium.[5]

Use[]

Dibutylmagnesium is used as a convenient reagent for the preparation of organomagnesium compounds.[3][6][7]

References[]

  1. ^ "Di-n-butylmagnesium solution 345113". Sigma Aldrich. Retrieved 3 June 2021.
  2. ^ Encyclopedia of Reagents for Organic Synthesis Dibutylmagnesium doi:org/10.1002/047084289X.rd063
  3. ^ a b Alan W. Duff, Peter B. Hitchcock u. a.: “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. 293, 1985, S. 271, doi:10.1016/0022-328X(85)80298-9.
  4. ^ Sigma-Aldrich Co., product no. {{{id}}}.
  5. ^ Google Patents: CN101362772A – Method for preparing dibutylmagnesium, abgerufen am 28. Oktober 2018.
  6. ^ Terry L. Rathman: Dibutylmagnesium. In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063.
  7. ^ Michael J. Michalczyk: Synthesis of magnesium hydride by the reaction of phenylsilane and dibutylmagnesium. In: Organometallics. 11, 1992, S. 2307, doi:10.1021/om00042a055.
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