Methylmagnesium chloride

Last updated
Methylmagnesium chloride
Methylmagnesiumchloride.svg
Names
IUPAC name
chlorido(methyl)magnesium
Other names
(chloromagnesio)methane
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.010.573 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 211-629-7
PubChem CID
UNII
  • InChI=1S/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1 Yes check.svgY
    Key: RQNMYNYHBQQZSP-UHFFFAOYSA-M Yes check.svgY
  • InChI=1/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1/rCH3Mg.ClH/c1-2;/h1H3;1H/q+1;/p-1
    Key: RQNMYNYHBQQZSP-OWCPXFRBAR
  • [Cl-].[Mg+]C
Properties
CH3MgCl
Molar mass 74.79 g/mol
Appearancecolorless solid
Reacts with water
Solubility soluble in diethyl ether and THF
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Flammable, Reacts with water
GHS labelling:
GHS-pictogram-flamme.svg GHS-pictogram-acid.svg
Danger
H225, H250, H260, H314
P210, P222, P223, P231+P232, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P334, P303+P361+P353, P304+P340, P305+P351+P338, P310, P321, P335+P334, P363, P370+P378, P402+P404, P403+P235, P405, P422, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 3: Short exposure could cause serious temporary or residual injury. E.g. chlorine gasFlammability 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. gasolineInstability 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
W
Flash point −17 °C (1 °F; 256 K)
Related compounds
Related compounds
 Phenylmagnesium bromide, Dibutylmagnesium
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

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.

Contents

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. Methylmagnesium-chloride-THF-3D-balls.png
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, ether solutions of methylmagnesium chloride reacts to give the insoluble coordination polymer with the formula MgCl2(dioxane)2. Remaining in the solution is the dioxane adduct of dimethylmagnesium. This conversion exploits the Schlenk equilibrium, which is driven to the right by the precipitation of the magnesium halide: [3]

2 CH3MgCl + 2 dioxane → (CH3)2Mg + MgCl2(dioxane)2

See also

Further reading

Related Research Articles

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<span class="mw-page-title-main">Zinc chloride</span> Chemical compound

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<span class="mw-page-title-main">Iron(II) chloride</span> Chemical compound

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<i>tert</i>-Butyl alcohol Chemical compound

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<span class="mw-page-title-main">Grignard reagent</span> Organometallic compounds used in organic synthesis

A Grignard reagent or Grignard compound is a chemical compound with the general formula R−Mg−X, where X is a halogen and R is an organic group, normally an alkyl or aryl. Two typical examples are methylmagnesium chloride Cl−Mg−CH3 and phenylmagnesium bromide (C6H5)−Mg−Br. They are a subclass of the organomagnesium compounds.

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<span class="mw-page-title-main">Dichloro(1,3-bis(diphenylphosphino)propane)nickel</span> Chemical compound

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<span class="mw-page-title-main">Chlorodiisopropylphosphine</span> Chemical compound

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<span class="mw-page-title-main">Dimethylthiocarbamoyl chloride</span> Chemical compound

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<span class="mw-page-title-main">Diethylphosphite</span> Chemical compound

Diethyl phosphite is the organophosphorus compound with the formula (C2H5O)2P(O)H. It is a popular reagent for generating other organophosphorus compounds, exploiting the high reactivity of the P-H bond. Diethyl phosphite is a colorless liquid. The molecule is tetrahedral.

<span class="mw-page-title-main">Isopropylmagnesium chloride</span> Chemical compound

Isopropylmagnesium chloride is an organometallic compound with the general formula (CH3)2HCMgCl. This highly flammable, colorless, and moisture sensitive material is the Grignard reagent derived from isopropyl chloride. It is commercially available, usually as a solution in tetrahydrofuran. This reagent is used to prepare Grignard reagents by transmetalation reactions as well as installing isopropyl groups. An illustrative generic reaction involves the generation of the Grignard reagent derived from bromo-3,5-bis(trifluoromethyl)benzene:

<span class="mw-page-title-main">(Trimethylsilyl)methyllithium</span> Chemical compound

(Trimethylsilyl)methyllithium is classified both as an organolithium compound and an organosilicon compound. It has the empirical formula LiCH2Si(CH3)3, often abbreviated LiCH2tms. It crystallizes as the hexagonal prismatic hexamer [LiCH2tms]6, akin to some polymorphs of methyllithium. Many adducts have been characterized including the diethyl ether complexed cubane [Li4(μ3-CH2tms)4(Et2O)2] and [Li2(μ-CH2tms)2(tmeda)2].

References

  1. ↑ Raymond Paul; Olivier Riobé; Michel Maumy (1976). "(E)-4-Hexen-1-ol". Org. Synth. 55: 62. doi:10.15227/orgsyn.055.0062.
  2. ↑ E. R. Coburn (1947). "3-Penten-2-ol". Org. Synth. 27: 65. doi:10.15227/orgsyn.027.0065.
  3. ↑ Fischer, Reinald; Görls, Helmar; Meisinger, Philippe R.; Suxdorf, Regina; Westerhausen, Matthias (2019). "Structure–Solubility Relationship of 1,4‐Dioxane Complexes of Di(hydrocarbyl)magnesium". Chemistry – A European Journal. 25 (55): 12830–12841. doi:10.1002/chem.201903120. PMC   7027550 . PMID   31328293.
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