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.
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, 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]
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.
^E. R. Coburn (1947). "3-Penten-2-ol". Org. Synth.27: 65. doi:10.15227/orgsyn.027.0065.
^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. PMC7027550. PMID 31328293.
January 01, 1970
methylmagnesium, chloride, organometallic, compound, with, general, formula, ch3mgcl, this, highly, flammable, colorless, moisture, sensitive, material, simplest, grignard, reagent, commercially, available, usually, solution, tetrahydrofuran, names, iupac, nam. 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 CAS Number 676 58 4 Y75 16 1 bromide Y 3D model JSmol Interactive image ChEBI CHEBI 51492 Y ChemSpider 10610396 Y ECHA InfoCard 100 010 573 EC Number 211 629 7 PubChem CID 12670 UNII M5E1132G4W Y22CW9773DF bromide Y CompTox Dashboard EPA DTXSID7052365 InChI InChI 1S CH3 ClH Mg h1H3 1H q 1 p 1 YKey RQNMYNYHBQQZSP UHFFFAOYSA M YInChI 1 CH3 ClH Mg h1H3 1H q 1 p 1 rCH3Mg ClH c1 2 h1H3 1H q 1 p 1Key RQNMYNYHBQQZSP OWCPXFRBAR SMILES Cl Mg C Properties Chemical formula CH3MgCl Molar mass 74 79 g mol Appearance colorless solid Solubility in water 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 Pictograms Signal word Danger Hazard statements H225 H250 H260 H314 Precautionary statements 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 332W 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 N verify what is Y N Infobox references Contents 1 Synthesis and reactions 2 See also 3 Further reading 4 ReferencesSynthesis and reactions editRelative 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 nbsp 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 2See also editMethylationFurther reading editSakai 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 edit Raymond Paul Olivier Riobe Michel Maumy 1976 E 4 Hexen 1 ol Org Synth 55 62 doi 10 15227 orgsyn 055 0062 E R Coburn 1947 3 Penten 2 ol Org Synth 27 65 doi 10 15227 orgsyn 027 0065 Fischer Reinald Gorls 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 Retrieved from https en wikipedia org w index php title Methylmagnesium chloride amp oldid 1177057262, wikipedia, wiki, book, books, library,
