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.[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

"Di-n-butylmagnesium solution 345113". Sigma Aldrich. Retrieved 3 June 2021.
Encyclopedia of Reagents for Organic Synthesis Dibutylmagnesium doi:10.1002/047084289X.rd063
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.
Sigma-Aldrich Co., product no. {{{id}}}.
Google Patents: CN101362772A – Method for preparing dibutylmagnesium, retrieved 28 October 2018.
Terry L. Rathman: Dibutylmagnesium. In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063.
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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[1] "Di-n-butylmagnesium solution 345113". Sigma Aldrich. Retrieved 3 June 2021.

[2] Encyclopedia of Reagents for Organic Synthesis Dibutylmagnesium doi:10.1002/047084289X.rd063

[DOI10.1016/0022-328X(85)80298-9-3] 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.

[Sigma2-4] Sigma-Aldrich Co., product no. {{{id}}}.

[google.com-5] Google Patents: CN101362772A – Method for preparing dibutylmagnesium, retrieved 28 October 2018.

[wiley.com-6] Terry L. Rathman: Dibutylmagnesium. In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063.

[DOI10.1021/om00042a055-7] Michael J. Michalczyk: Synthesis of magnesium hydride by the reaction of phenylsilane and dibutylmagnesium. In: Organometallics. 11, 1992, S. 2307, doi:10.1021/om00042a055.