Methyl magnesium bromide

Structural formula
General
Surname	Methyl magnesium bromide
other names	Bromomethyl Magnesium
Molecular formula	CH 3 MgBr
External identifiers / databases
EC number	200-844-1
ECHA InfoCard	100,000,768
PubChem	6349
Wikidata	Q9667145
properties
Molar mass	119.24 g mol −1
density	1.035 g cm −3 (25 ° C)
solubility	soluble in ether and THF; practically insoluble in benzene;
safety instructions
H and P phrases	H: 225-260-302-314-336
	P: 210-223-231 + 232-261-370 + 378-422
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

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

Extraction and presentation

Methyl magnesium bromide can be obtained by reacting magnesium with methyl bromide .

{\ displaystyle {\ ce {CH3Br + Mg -> CH3MgBr}}}

properties

Methyl magnesium bromide is marketed commercially as a solution in diethyl ether or 2-methyltetrahydrofuran .

use

Methyl magnesium bromide is used to make other chemical compounds (such as clemastine ). Cram selectivity occurs in the addition of methyl magnesium bromide to α- chiral aldehydes and ketones that do not contain a heteroatom at the α stereocenter .

safety instructions

Since the heat of decomposition of Grignard reagents with water is great and the solvents in which they are dissolved become highly volatile and flammable, they must be handled with extreme care. In particular, the solution of methyl magnesium bromide in diethyl ether can spontaneously ignite on contact with water or even damp soil.

Individual evidence

↑ ^a ^b ^c ^d data sheet Methylmagnesium bromide solution, 3.0 M in diethyl ether from Sigma-Aldrich , accessed on April 12, 2018 ( PDF ).
^ ^A ^b William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2016, ISBN 978-1-4665-7115-0 , pp. 380 ( limited preview in Google Book search).
^ Robert A. Lewis: Hawley's Condensed Chemical Dictionary . Ed .: Richard J. Lewis, Michael D Larrañaga. John Wiley & Sons Inc., 2016, ISBN 978-1-118-13515-0 , pp. 911 ( limited preview in Google Book Search).
↑ Data sheet Methylmagnesium bromide, 35% (3.2M) in 2-MeTHF, packaged under Argon in resealable septum cap bottles from AlfaAesar, accessed on April 12, 2018 ( PDF )(JavaScript required) .
^ Fv Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 983 ( limited preview in Google Book Search).
↑ Organic chemistry. [Main volume] Walter de Gruyter, 1980, ISBN 978-3-11-082970-9 , pp. 783 ( limited preview in Google Book search).
↑ ^a ^b Reinhard Brückner: reaction mechanisms, organic reactions, stereochemistry, modern synthesis methods . Springer-Verlag, 2014, ISBN 978-3-662-45684-2 , pp. 440 ( limited preview in Google Book Search).
^ Robert A. Lewis: Hawley's Condensed Chemical Dictionary . John Wiley & Sons, 2016, ISBN 978-1-119-19372-2 , pp. 686 ( limited preview in Google Book Search).

[Sigma-1] ta sheet Methylmagnesium bromide solution, 3.0 M in diethyl ether from Sigma-Aldrich , accessed on April 12, 2018 ( PDF ).

[William_M._Haynes-2] A ^b William M. Haynes: CRC Handbook of Chemistry and Physics, 94th Edition . CRC Press, 2016, ISBN 978-1-4665-7115-0 , pp. 380 ( limited preview in Google Book search).

[Hawley's-3] Robert A. Lewis: Hawley's Condensed Chemical Dictionary . Ed .: Richard J. Lewis, Michael D Larrañaga. John Wiley & Sons Inc., 2016, ISBN 978-1-118-13515-0 , pp. 911 ( limited preview in Google Book Search).

[Alfa-4] Data sheet Methylmagnesium bromide, 35% (3.2M) in 2-MeTHF, packaged under Argon in resealable septum cap bottles from AlfaAesar, accessed on April 12, 2018 ( PDF )(JavaScript required) .

[F.v._Bruchhausen,_S._Ebel,_A.W._Frahm,_E._Hackenthal-5] Fv Bruchhausen, S. Ebel, AW Frahm, E. Hackenthal: Hager's handbook of pharmaceutical practice substances AD . Springer-Verlag, 2013, ISBN 978-3-642-57995-0 , pp. 983 ( limited preview in Google Book Search).

[6] Organic chemistry. [Main volume] Walter de Gruyter, 1980, ISBN 978-3-11-082970-9 , pp. 783 ( limited preview in Google Book search).

[Reinhard_Brückner-7] Reinhard Brückner: reaction mechanisms, organic reactions, stereochemistry, modern synthesis methods . Springer-Verlag, 2014, ISBN 978-3-662-45684-2 , pp. 440 ( limited preview in Google Book Search).

[Robert_A._Lewis-8] Robert A. Lewis: Hawley's Condensed Chemical Dictionary . John Wiley & Sons, 2016, ISBN 978-1-119-19372-2 , pp. 686 ( limited preview in Google Book Search).