Methyl magnesium chloride

Structural formula
General
Surname	Methyl magnesium chloride
other names	Chloromethylmagnesium
Molecular formula	CH 3 ClMg
Brief description	gray liquid (dissolved in THF)
External identifiers / databases
EC number	211-629-7
ECHA InfoCard	100.010.573
PubChem	12670
Wikidata	Q392954
properties
Molar mass	74.79 g mol −1
Physical state	liquid
solubility	soluble in tetrahydrofuran; insoluble in petroleum ether and benzene;
safety instructions
H and P phrases	H: 225-260-302-314-335-351
	EUH: 014-019
	P: 210-231 + 232-280-370 + 378-402 + 404-403 + 235
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Methyl magnesium chloride is a chemical compound from the group of Grignard compounds , which belong to the organometallic compounds .

Extraction and presentation

Methyl magnesium chloride can be obtained by reacting methyl chloride with magnesium in tetrahydrofuran :

{\ displaystyle \ mathrm {CH_ {3} Cl \ + \ Mg \ {\ xrightarrow {THF}} \ CH_ {3} MgCl}}

properties

Methyl magnesium chloride is commercially available as a solution in tetrahydrofuran and in this case is a gray liquid. At temperatures below 5 ° C, methyl magnesium chloride can crystallize out as a solid.

use

Methyl magnesium chloride is used as a Grignard reagent in the synthesis of organic compounds (e.g. in nucleophilic substitutions ). The lower reactivity towards methyl magnesium bromide allows milder reaction conditions.

It can also be used to determine the molecular weight of carboxylic acids. For this purpose, the methane released during the reaction of methyl magnesium chloride and carboxylic acid is determined volumetrically.

Individual evidence

↑ ^a ^b ^c ^d ^e data sheet Methylmagnesium chloride solution, 3.0 M in THF from Sigma-Aldrich , accessed on October 14, 2017 ( PDF ).
^ CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 380 ( books.google.de ).
↑ Parts of the labeling of hazardous substances relate to the hazards caused by the solvent.
↑ Michael T. Holbrook: Kirk-Othmer Encyclopedia of Chemical Technology: Methyl Chloride. doi: 10.1002 / 0471238961.1305200808151202.a01.pub2
^ Methylmagnesium chloride in THF. (PDF; 199 kB) FMC Lithium, accessed on October 14, 2017 (English).
↑ Patrick Groß: The total synthesis of (+) - fumimycin . Ed .: Stefan Bräse. Logos Verlag, Berlin 2010, ISBN 978-3-8325-2571-2 , p. 37 ( limited preview in Google Book search).
↑ Reinhard Brückner: reaction mechanisms: organic reactions, stereochemistry, modern synthesis methods . 3. Edition. Springer-Verlag, Berlin / Heidelberg 2015, ISBN 978-3-662-45684-2 , p. 315 ( limited preview in Google Book search).

[Sigma-1] ↑ ^a ^b ^c ^d ^e data sheet Methylmagnesium chloride solution, 3.0 M in THF from Sigma-Aldrich , accessed on October 14, 2017 ( PDF ).

[2] CRC Handbook of Chemistry and Physics, 97th Edition . CRC Press, 2016, ISBN 978-1-4987-5429-3 , pp. 380 ( books.google.de ).

[LM-3] Parts of the labeling of hazardous substances relate to the hazards caused by the solvent.

[Holbrook-4] Michael T. Holbrook: Kirk-Othmer Encyclopedia of Chemical Technology: Methyl Chloride. doi: 10.1002 / 0471238961.1305200808151202.a01.pub2

[5] Methylmagnesium chloride in THF. (PDF; 199 kB) FMC Lithium, accessed on October 14, 2017 (English).

[6] Patrick Groß: The total synthesis of (+) - fumimycin . Ed .: Stefan Bräse. Logos Verlag, Berlin 2010, ISBN 978-3-8325-2571-2 , p. 37 ( limited preview in Google Book search).

[7] Reinhard Brückner: reaction mechanisms: organic reactions, stereochemistry, modern synthesis methods . 3. Edition. Springer-Verlag, Berlin / Heidelberg 2015, ISBN 978-3-662-45684-2 , p. 315 ( limited preview in Google Book search).