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Methylmagnesium chloride: Difference between revisions

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Revision as of 17:19, 7 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report errors or [[user talk:CheMoBo← Previous edit Latest revision as of 15:48, 24 December 2024 edit undoCitation bot (talk | contribs)Bots5,455,445 edits Altered title. | Use this bot. Report bugs. | Suggested by Whoop whoop pull up | Category:Methylating agents | #UCB_Category 15/23 
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{{chembox|Verifiedfields=changed|Watchedfields=changed|verifiedrevid=448966509
{{chembox
⚫ |ImageFile=Methylmagnesiumchloride.svg
| verifiedrevid = 444014054
⚫ |ImageSize=|ImageCaption=
| ImageFile = Methylmagnesium-chloride-THF-3D-balls.png
|IUPACName=chlorido(methyl)magnesium
⚫ | ImageSize =
|OtherNames=(chloromagnesio)methane
| IUPACName = chloridomethylmagnesium
⚫ |Section1={{Chembox Identifiers
| OtherNames =
⚫ | CASNo = 676-58-4
⚫ | Section1 = {{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASNo2_Ref = {{cascite|correct|CAS}}
| CASNo2 = 75-16-1
⚫ | CASNo2_Comment = (bromide) <!-- Also CAS verified -->
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 51492
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 10610396 | ChemSpiderID = 10610396
| EC_number = 211-629-7
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = M5E1132G4W
| UNII2_Ref = {{fdacite|correct|FDA}}
| UNII2 = 22CW9773DF
| UNII2_Comment = (bromide)
⚫ | PubChem = 12670
| InChI = 1/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1/rCH3Mg.ClH/c1-2;/h1H3;1H/q+1;/p-1 | InChI = 1/CH3.ClH.Mg/h1H3;1H;/q;;+1/p-1/rCH3Mg.ClH/c1-2;/h1H3;1H/q+1;/p-1
| InChIKey = RQNMYNYHBQQZSP-OWCPXFRBAR | InChIKey = RQNMYNYHBQQZSP-OWCPXFRBAR
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = RQNMYNYHBQQZSP-UHFFFAOYSA-M | StdInChIKey = RQNMYNYHBQQZSP-UHFFFAOYSA-M
⚫ | CASNo = 676-58-4
⚫ | CASNo_Ref = {{cascite|correct|CAS}}
⚫ | CASOther = <br/>75-16-1 (bromide) <!-- Also CAS verified -->
⚫ | PubChem =
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | ChEBI = 51492
| SMILES = .C | SMILES = .C
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = CH<sub>3</sub>MgCl | Formula = CH<sub>3</sub>MgCl
| MolarMass = 74.79 g/mol | MolarMass = 74.79 g/mol
| Appearance = | Appearance = colorless solid
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = | Solubility = Reacts with water
| SolubleOther = soluble in ] and ]
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards = Flammable, Reacts with water
| FlashPt = | NFPA-H = 3
| Autoignition = | NFPA-F = 3
| NFPA-R = 2
| NFPA-S = W
| FlashPtC = -17
| AutoignitionPtC =
| GHSPictograms = {{GHS02}}{{GHS05}}
| GHSSignalWord = Danger
| HPhrases = {{H-phrases|225|250|260|314}}
| PPhrases = {{P-phrases|210|222|223|231+232|233|240|241|242|243|260|264|280|301+330+331|302+334|303+361+353|304+340|305+351+338|310|321|335+334|363|370+378|402+404|403+235|405|422|501}}
}} }}
| Section7 = {{Chembox Other |Section7={{Chembox Related
| OtherCpds = ] | OtherCompounds = ], ]
}} }}}}
'''Methylmagnesium chloride''' is an ] compound with the general formula CH<sub>3</sub>MgCl. This highly flammable, colorless, and moisture sensitive material is the simplest ] and is commercially available, usually as a solution in ].
}}
'''Methylmagnesium chloride''' is a commercially available ]. Like ], it is the synthetic equivalent to the ] carbanion ]. It is usually sold as a solution in ]. The model of the molecule shows methylmagnesium chloride with the magnesium atom in the center. Two molecules of ] (in the upper part of the drawing) coordinate by their oxygen atoms to magnesium.


==Synthesis and reactions==
this is a moisture sensitive compound.
Relative to the more commonly encountered methylmagnesium bromide<ref>{{cite journal|journal=]|year=1976|volume=55|page=62|doi=10.15227/orgsyn.055.0062|title=(E)-4-Hexen-1-ol|author=Raymond Paul |author2=Olivier Riobé |author3=Michel Maumy }}</ref> and methylmagnesium iodide, methylmagnesium chloride offers the advantages of low equivalent weight and low cost. It is prepared by the reaction of ] and magnesium in ].<ref>{{cite journal|journal=]|year=1947|volume=27|page=65|doi=10.15227/orgsyn.027.0065|title=3-Penten-2-ol|author=E. R. Coburn}}</ref>


]


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

Like ], it is the synthetic equivalent to the ] carbanion ]. It reacts with water and other protic reagents to give methane, e.g.,:
:CH<sub>3</sub>MgCl + ROH → CH<sub>4</sub> + MgCl(OR)

When treated with ], ether solutions of methylmagnesium chloride reacts to give the insoluble ] with the formula MgCl<sub>2</sub>(dioxane)<sub>2</sub>. Remaining in the solution is the dioxane adduct of ]. This conversion exploits the ], which is driven to the right by the precipitation of the magnesium halide:<ref>{{cite journal |doi=10.1002/chem.201903120|title=Structure–Solubility Relationship of 1,4-Dioxane Complexes of Di(hydrocarbyl)magnesium |year=2019 |last1=Fischer |first1=Reinald |last2=Görls |first2=Helmar |last3=Meisinger |first3=Philippe R. |last4=Suxdorf |first4=Regina |last5=Westerhausen |first5=Matthias |journal=Chemistry – A European Journal |volume=25 |issue=55 |pages=12830–12841 |pmid=31328293 |pmc=7027550 }}</ref>
:2 CH<sub>3</sub>MgCl + 2 dioxane → (CH<sub>3</sub>)<sub>2</sub>Mg + MgCl<sub>2</sub>(dioxane)<sub>2</sub>


==See also== ==See also==
* ] * ]


==Further reading==
*{{cite journal|doi=10.1021/ja00378a047|title=Ab initio study of the structure and vibrational frequencies of the Grignard reagent methylmagnesium chloride|year=1982|last1=Sakai|first1=Shogo|last2=Jordan|first2=K. D.|journal=]|volume=104|issue=14|page=4019}}


==References==
⚫ ]
<references />


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