Jump to content

Dibutylmagnesium: Difference between revisions

From Wikipedia, the free encyclopedia
Browse history interactively
← Previous edit
Content deleted Content added
VisualWikitext
 
(9 intermediate revisions by 8 users not shown)
Line 32: Line 32:
| GHSPictograms = {{GHS02}} {{GHS05}} {{GHS07}} {{GHS08}} {{GHS09}}
| GHSPictograms = {{GHS02}} {{GHS05}} {{GHS07}} {{GHS08}} {{GHS09}}
| GHSSignalWord = Danger
| GHSSignalWord = Danger
| HPhrases = {{H-Phrases|250|260|314}}
| HPhrases = {{H-phrases|250|260|314}}
| PPhrases = {{P-phrases|210|222|223|231+232|260|264|280|301+330+331|302+334|303+361+353|304+340|305+351+338|303+361+353|310|321|335+334|370+378|402+404|405|422|501}}
| PPhrases = {{P-phrases|210|222|223|231+232|260|264|280|301+330+331|302+334|303+361+353|304+340|305+351+338|310|321|335+334|370+378|402+404|405|422|501}}
| FlashPtC =
| FlashPtC =
| AutoignitionPt = }}
| AutoignitionPt = }}
Line 41: Line 41:
}}
}}


'''Dibutylmagnesium''' is an [[organometallic]] chemical compound of [[magnesium]]. Its chemical formula is {{chem|C|8|H|18|Mg}}.<ref>{{cite web |title=Di-n-butylmagnesium solution 345113 |url=https://www.sigmaaldrich.com/catalog/product/aldrich/345113?lang=en&region=RU |publisher=[[Sigma Aldrich]] |access-date=3 June 2021}}</ref> Dibutylmagnesium is a chemical compound from the group of [[organomagnesium compound]]s. The pure substance is a waxy solid. Commercially, it is marketed as solution in [[heptane]].<ref>[[Encyclopedia of Reagents for Organic Synthesis]] ''Dibutylmagnesium'' [[doi:org/10.1002/047084289X.rd063]]</ref>
'''Dibutylmagnesium''' is an [[organometallic]] chemical compound of [[magnesium]]. Its chemical formula is {{chem|C|8|H|18|Mg}}.<ref name=Sigma /> Dibutylmagnesium is a chemical compound from the group of [[organomagnesium compound]]s. The pure substance is a waxy solid. Commercially, it is marketed as solution in [[heptane]].<ref name=Encyc />


==Synthesis==
==Synthesis==
Dibutylmagnesium can be obtained by reaction of [[butyllithium]] with magnesium butylchloride and subsequent addition of magnesium 2-ethylhexanoate.<ref name="DOI10.1016/0022-328X(85)80298-9" /> The compound can also be prepared by hydrogenation of magnesium, followed by reaction with [[1-butene]].<ref name="Sigma2">{{Sigma-Aldrich|Aldrich|731110|Name=Di-n-butylmagnesium solution, 1 M in ether and hexanes|Abruf=2018-10-28}}</ref> It is also possible to prepare dibutylmagnesium using [[2-chlorobutane]], magnesium powder, and [[n-butyllithium]].<ref name="google.com">Google Patents: [https://patents.google.com/patent/CN101362772A/en CN101362772A – Method for preparing dibutylmagnesium], abgerufen am 28. Oktober 2018.</ref>
Dibutylmagnesium can be obtained by reaction of [[butyllithium]] with magnesium butylchloride and subsequent addition of magnesium 2-ethylhexanoate.<ref name=Orig /> The compound can also be prepared by hydrogenation of magnesium, followed by reaction with [[1-butene]].<ref name="Sigma" /> It is also possible to prepare dibutylmagnesium using [[2-chlorobutane]], magnesium powder, and [[n-butyllithium]].<ref name=Patent />


==Use==
==Use==
Dibutylmagnesium is used as a convenient reagent for the preparation of [[organomagnesium compound]]s.<ref name=Orig /><ref name=Encyc /><ref name=TransMet />
⚫
Dibutylmagnesium is used as a convenient reagent for the preparation of [[organomagnesium compound]]s.<ref name="DOI10.1016/0022-328X(85)80298-9">Alan W. Duff, Peter B. Hitchcock u.&nbsp;a.: ''“Dibutylmagnesium”, a convenient reagent for the synthesis of useful organic magnesium reagents MgA<sub>2</sub> including cyclopentadienyls, aryloxides, and amides. Preparation of Zr(C5H5)Cl3. X-ray structure of [{μ-N(SiMe)<sub>3</sub>C<sub>6</sub>H<sub>4</sub>N}(SiMe<sub>3</sub>)-o(OEt<sub>2</sub>)]<sub>2</sub>.'' In: ''[[Journal of Organometallic Chemistry]].'' 293, 1985, S.&nbsp;271, {{DOI|10.1016/0022-328X(85)80298-9}}.</ref><ref name="wiley.com">Terry L. Rathman: ''Dibutylmagnesium''. In: ''[[Encyclopedia of Reagents for Organic Synthesis]]'', 2001, [[doi:10.1002/047084289X.rd063]].</ref><ref name="DOI10.1021/om00042a055">Michael J. Michalczyk: ''Synthesis of magnesium hydride by the reaction of phenylsilane and dibutylmagnesium.'' In: ''[[Organometallics]].'' 11, 1992, S.&nbsp;2307, {{DOI|10.1021/om00042a055}}.</ref>


==References==
==References==
<references>
{{Reflist}}
<ref name=Encyc>Terry&nbsp;L. Rathman: "Dibutylmagnesium". In:&nbsp;''[[Encyclopedia of Reagents for Organic Synthesis]]'', 2001, [[doi:10.1002/047084289X.rd063]]</ref>
⚫
<ref name=Orig>Alan&nbsp;W. Duff, Peter&nbsp;B. Hitchcock, ''et&nbsp;al'': "'Dibutylmagnesium', a convenient reagent for the synthesis of useful organic magnesium reagents MgA<sub>2</sub> including cyclopentadienyls, aryloxides, and amides. Preparation of Zr(C<sub>5</sub>H<sub>5</sub>)Cl<sub>3</sub>. X-ray structure of [{μ-N(SiMe)<sub>3</sub>C<sub>6</sub>H<sub>4</sub>N}(SiMe<sub>3</sub>)-o(OEt<sub>2</sub>)]<sub>2</sub>." In:&nbsp;''[[Journal of Organometallic Chemistry]].'' Issue&nbsp;293 (1985), p.&nbsp;271, {{doi|10.1016/0022-328X(85)80298-9}}.</ref>
<ref name=Patent>"[https://patents.google.com/patent/CN101362772A/en Method for preparing dibutylmagnesium]" (Patent CN101362772A), retrieved via [[Google Patents]] 28&nbsp;October 2018.</ref>
<ref name=Sigma>{{Sigma-Aldrich|id=731110|name=Di-n-butylmagnesium solution, 1 M in ether and hexanes|accessdate=2018-10-28}}</ref>
<ref name=TransMet>Michael&nbsp;J. Michalczyk: "Synthesis of magnesium hydride by the reaction of phenylsilane and dibutylmagnesium." In:&nbsp;''[[Organometallics]].'' Issue&nbsp;11 (1992), p.&nbsp;2307, {{doi|10.1021/om00042a055}}.</ref>
</references>


[[Category:Magnesium compounds]]
[[Category:Magnesium compounds]]
[[Category:Organomagnesium compounds]]
[[Category:Organomagnesium compounds]]
[[Category:Butyl compounds]]
[[Category:Pyrophoric materials]]

Latest revision as of 06:37, 10 June 2024

Dibutylmagnesium
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
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).

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

[edit]

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

[edit]

Dibutylmagnesium is used as a convenient reagent for the preparation of organomagnesium compounds.[3][2][5]

References

[edit]
  1. ^ a b Sigma-Aldrich Co., Di-n-butylmagnesium solution, 1 M in ether and hexanes. Retrieved on 2018-10-28.
  2. ^ a b Terry L. Rathman: "Dibutylmagnesium". In: Encyclopedia of Reagents for Organic Synthesis, 2001, doi:10.1002/047084289X.rd063
  3. ^ a b 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.
Retrieved from "https://en.wikipedia.org/enwiki/w/index.php?title=Dibutylmagnesium&oldid=1228248184"