Dibutylmagnesium

Dibutylmagnesium

Names
Other names Di-n-butylmagnesium
Identifiers
CAS Number	1191-47-5  Y
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/c2*1-3-4-2;/h2*1,3-4H2,2H3;/q2*-1;+2 Key: KJJBSBKRXUVBMX-UHFFFAOYSA-N
SMILES CCC[CH2-].CCC[CH2-].[Mg+2]
Properties
Chemical formula	(CH3CH2CH2CH2)2Mg
Molar mass	138.537 g·mol−1
Appearance	Waxy white solid
Density	0.713 g/mL at 25°C
Solubility in water	Reacts with water
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 (CH₃CH₂CH₂CH₂)₂Mg. ^[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 butylmagnesium chloride 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

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