Dibutylmagnesium

Dibutylmagnesium
Names
	Other names Di-n-butylmagnesium
Identifiers
CAS Number	1191-47-5 ;
3D model (JSmol)	Interactive image;
ChemSpider	10659503;
ECHA InfoCard	100.013.397
EC Number	214-736-7;
PubChem CID	70929;
CompTox Dashboard (EPA)	DTXSID9061590 ;
	InChI InChI=1S/2C4H9.Mg/c21-3-4-2;/h21,3-4H2,2H3;/q2*-1;+2 Key: KJJBSBKRXUVBMX-UHFFFAOYSA-N;
	SMILES CCC[CH2-].CCC[CH2-].[Mg+2];
Properties
Chemical formula	C; 8H; 18Mg
Molar mass	138.53
Appearance	Waxy solid
Density	0.713 g/mL at 25°C
Hazards
	GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H250, H260, H314
Precautionary statements	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.[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

Sigma-Aldrich Co., Di-n-butylmagnesium solution, 1 M in ether and hexanes. Retrieved on 2018-10-28.
Terry L. Rathman: "Dibutylmagnesium". In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063
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.

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[Sigma-1] Sigma-Aldrich Co., Di-n-butylmagnesium solution, 1 M in ether and hexanes. Retrieved on 2018-10-28.

[Encyc-2] Terry L. Rathman: "Dibutylmagnesium". In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063

[Orig-3] 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.

[Patent-4] "Method for preparing dibutylmagnesium" (Patent CN101362772A), retrieved via Google Patents 28 October 2018.

[TransMet-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.