Dibutyl magnesium

Structural formula
General
Surname	Dibutyl magnesium
other names	Di- n -butyl magnesium; DBM;
Molecular formula	C 8 H 18 Mg
External identifiers / databases
ECHA InfoCard	100.013.397
PubChem	70929
Wikidata	Q57904232
properties
Molar mass	138.53 g mol −1
density	0.713 g cm −3 (25 ° C)
solubility	soluble in heptane
safety instructions
H and P phrases	H: 225-250-260-304-314-336-410
	P: 210-231 + 232-280-305 + 351 + 338-370 + 378-422
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Dibutylmagnesium is a chemical compound from the group of organic magnesium compounds . The pure substance is a waxy solid. It is sold commercially as a 1 M solution in heptane , this has a density of 0.72 g cm ⁻³ , and a viscosity of 0.91 cP at 25 ° C and 0.76 cP at 35 ° C

Extraction and presentation

Dibutylmagnesium can be obtained by reacting butyllithium to form magnesium butyl chloride and then adding magnesium 2-ethylhexanoate . The compound can also be prepared by hydrogenation of magnesium followed by reaction with 1-butene . It is also possible to produce dibutylmagnesium using 2-chlorobutane , magnesium powder and n- butyllithium.

use

Dibutyl magnesium is used to make organomagnesium compounds.

Individual evidence

↑ ^a ^b ^c ^d data sheet Di-n-butylmagnesium solution, 1.0 M in heptane from Sigma-Aldrich , accessed on October 28, 2018 ( PDF ).
↑ Encyclopedia of Reagents for Organic Synthesis Dibutylmagnesium doi: org / 10.1002 / 047084289X.rd063
↑ ^a ^b Alan W. Duff, Peter B. Hitchcock u. a .: “Dibutylmagnesium”, a convenient reagent for the synthesis of useful organic magnesium reagents MgA ₂ including cyclopentadienyls, aryloxides, and amides. Preparation of Zr (C5H5) Cl3. X-ray structure of [{μ-N (SiMe) ₃ C ₆ H ₄ N} (SiMe ₃ ) -o (OEt ₂ )] ₂ . In: Journal of Organometallic Chemistry . 293, 1985, p. 271, doi : 10.1016 / 0022-328X (85) 80298-9 .
↑ Data sheet Di-n-butylmagnesium solution, 1 M in ether and hexanes from Sigma-Aldrich , accessed on October 28, 2018 ( PDF ).
↑ Google Patents: CN101362772A - Method for preparing dibutylmagnesium , accessed October 28, 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, p. 2307, doi : 10.1021 / om00042a055 .

[Sigma-1] ta sheet Di-n-butylmagnesium solution, 1.0 M in heptane from Sigma-Aldrich , accessed on October 28, 2018 ( PDF ).

[2] Encyclopedia of Reagents for Organic Synthesis Dibutylmagnesium doi: org / 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 MgA ₂ including cyclopentadienyls, aryloxides, and amides. Preparation of Zr (C5H5) Cl3. X-ray structure of [{μ-N (SiMe) ₃ C ₆ H ₄ N} (SiMe ₃ ) -o (OEt ₂ )] ₂ . In: Journal of Organometallic Chemistry . 293, 1985, p. 271, doi : 10.1016 / 0022-328X (85) 80298-9 .

[Sigma2-4] Data sheet Di-n-butylmagnesium solution, 1 M in ether and hexanes from Sigma-Aldrich , accessed on October 28, 2018 ( PDF ).

[google.com-5] Google Patents: CN101362772A - Method for preparing dibutylmagnesium , accessed October 28, 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, p. 2307, doi : 10.1021 / om00042a055 .