Methyl magnesium iodide

Structural formula
General
Surname	Methyl magnesium iodide
other names	Iodomethylmagnesium
Molecular formula	CH 3 MgI
External identifiers / databases
CAS number 917-64-6 ECHA InfoCard 100,011,847 PubChem 101907 ChemSpider 10254344 Wikidata Q58215242
properties
Molar mass	166.24 g mol −1
Physical state	liquid
density	1.261 g cm −3 (25 ° C)
safety instructions
GHS labeling of hazardous substances Solution in diethyl ether danger H and P phrases H: 225-260-314-336 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 iodide is a chemical compound from the group of organomagnesium compounds .

Extraction and presentation

Methyl magnesium iodide can be obtained in an ethereal solution by reacting iodomethane and magnesium shavings. The compound forms dimeric structures in solution, which are described by the Schlenk equilibrium .

use

Methyl magnesium iodide is used in organic synthesis. In Grignard reactions with the compound, additions to carbonyl compounds produce secondary or tertiary alcohols , and α-branched amines to imines or nitriles . The compound opens epoxides to alcohols. Methyl element compounds are obtained by reaction with element halides. In organic analysis, methyl magnesium iodide is used to determine Zerewitinoff (see active hydrogen).

Individual evidence

1. ↑ ^{a b c d} data sheet Methylmagnesium iodide solution, 3.0 M in diethyl ether from Sigma-Aldrich , accessed on January 30, 2019 ( PDF ).
2. ↑ ^{a b} Entry on methyl magnesium iodide. In: Römpp Online . Georg Thieme Verlag, accessed on January 30, 2019.