Methylmagnesium chloride

Methylmagnesium chloride is an organometallic compound with the general formula CH3MgCl. This highly flammable, colorless, and moisture sensitive material is the simplest Grignard reagent and is commercially available, usually as a solution in tetrahydrofuran.

Methylmagnesium chloride
Names
IUPAC name
chlorido(methyl)magnesium
Other names
(chloromagnesio)methane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.573
UNII
Properties
CH3MgCl
Molar mass 74.79 g/mol
Appearance colorless solid
Reacts with water
Solubility soluble in diethyl ether and THF
Hazards
Main hazards Flammable, Reacts with water
NFPA 704 (fire diamond)
Flammability code 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineHealth code 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasReactivity code 2: Undergoes violent chemical change at elevated temperatures and pressures, reacts violently with water, or may form explosive mixtures with water. E.g. white phosphorusSpecial hazard W: Reacts with water in an unusual or dangerous manner. E.g. sodium, sulfuric acid
3
3
2
Flash point -17°C
Related compounds
Related compounds
 Phenylmagnesium bromide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Synthesis and reactions

Relative to the more commonly encountered methylmagnesium bromide[1] and methylmagnesium iodide, methylmagnesium chloride offers the advantages of low equivalent weight and low cost. It is prepared by the reaction of methyl chloride and magnesium in ethyl ether.[2]

Structure of CH3MgCl(thf)2, which is representative of the species in donor solvents.

As with most Grignard reagents, methylmagnesium chloride is highly solvated by ether solvents via coordination from two oxygen atoms to give a tetrahedrally bonded magnesium center.

Like methyllithium, it is the synthetic equivalent to the methyl carbanion synthon. It reacts with water and other protic reagents to give methane, e.g.,:

CH3MgCl + ROH → CH4 + MgCl(OR)

When treated with dioxane, methylmagnesium chloride converts to dimethylmagnesium via the Schlenk equilibrium:

2 CH3MgCl + dioxane → (CH3)2Mg + MgCl2(dioxane)
gollark: No, I'm just using some audio routing hax™ to play https://www.youtube.com/watch?v=WQPncqz6PoI into voice chat.
gollark: This is NOT true. I have not in any way been sponsored by pizza companies. There have been no advertising agreements whatsoever with any companies producing pizza or otherwise to have me subliminally advertise pizza, as my profile picture is not a pizza. Since it is not a pizza, this is obviously not pizza advertisement whatsoever. No monetary exchanges or otherwise have occurred with companies engaged in pizza production for any reason relating to my profile picture. You are clearly engaged in libel and attempting to discredit my non-pizza-advertising status. It is IN NO WAY subliminal pizza advertising because I DO NOT work for pizza companies in any form. It's not pizza. There were no deals, under-the-table or otherwise, with pizza companies. No pizza companies pay for any kind of subliminal advertising involving me. People make that mistake, but I am not working for pizza companies doing subliminal advertising; that is not in any way what I am doing. I am NOT being sponsored by ANY pizza companies to display subliminal pizza advertising OF ANY KIND.
gollark: I am engaging in music.
gollark: I disagree.
gollark: I agree, it does NOT need to be much more complex than "send PNGs and metadata over, poll for print status".

See also

Further reading
  • Sakai, Shogo; Jordan, K. D. (1982). "Ab initio study of the structure and vibrational frequencies of the Grignard reagent methylmagnesium chloride". Journal of the American Chemical Society. 104 (14): 4019. doi:10.1021/ja00378a047.

References
  1. Raymond Paul, Olivier Riobé, Michel Maumy (1976). "(E)-4-Hexen-1-ol". Org. Synth. 55: 62. doi:10.15227/orgsyn.055.0062.CS1 maint: uses authors parameter (link)
  2. E. R. Coburn (1947). "3-Penten-2-ol". Org. Synth. 27: 65. doi:10.15227/orgsyn.027.0065.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.