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Revision as of 16:40, 12 May 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChemSpiderID_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEMBL_Ref', 'KEGG_Ref') per Chem/Drugbox validation (← Previous edit		Latest revision as of 19:14, 29 September 2022 edit undoOlliverWithDoubleL (talk | contribs)Extended confirmed users24,701 edits chem formatting
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			{{Short description|Ionic compound with the formula I}}
	{{chembox		{{chembox
			| Verifiedfields = changed
	| verifiedrevid = 399920468		| verifiedrevid = 428779443
	| Name = Eschenmoser's salt		| Name = Eschenmoser's salt
	| ImageFile = Eschenmosersalz.png		| ImageFile = Eschenmosersalz.png
	| ImageSize = 120px
	| ImageName = Eschenmoser's salt		| ImageSize = 120px
			| ImageName = Eschenmoser's salt
	| IUPACName = Dimethylmethylideneammonium iodide		| PIN = ''N'',''N''-Dimethylmethaniminium iodide
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| SMILES = C(C)=C.		| SMILES = C(C)=C.
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 2006292		| ChemSpiderID = 2006292
	| PubChem = 2724133		| PubChem = 2724133
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	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = VVDUZZGYBOWDSQ-UHFFFAOYSA-M		| StdInChIKey = VVDUZZGYBOWDSQ-UHFFFAOYSA-M
			| CASNo_Ref = {{cascite|correct|??}}
	| CASNo = 33797-51-2		| CASNo = 33797-51-2
	| CASOther = <br>(Iodide) (Chloride)		| CASNo_Comment = (Iodide)
			| CASNo2_Ref = {{cascite|changed|??}}
⚫	| RTECS =
			| CASNo2 = 30354-18-8
			| CASNo2_Comment = (Chloride)
			| UNII_Ref = {{fdacite|correct|FDA}}
			| UNII = 5C42I004S1
		⚫	| RTECS =
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| Formula = C<sub>3</sub>H<sub>8</sub>NI		| Formula = {{chem2|C3H8NI}}
	| MolarMass = 185.01 g/mol		| MolarMass = 185.01 g/mol
	| Appearance = colorless hygroscopic crystals		| Appearance = colorless hygroscopic crystals
	| Solubility = decomp.		| Solubility = decomposes
	| MeltingPtC = 116		| MeltingPtC = 116
	}}		}}
	| Section7 = {{Chembox Hazards		|Section7={{Chembox Hazards
	| ExternalMSDS =		| ExternalSDS =
	| MainHazards =		| MainHazards =
	| FlashPt =		| FlashPt =
			| GHS_ref=
	| RPhrases = {{R36/37/38}}
	| SPhrases = {{S26}} {{S36}}		| GHSPictograms = {{GHS07}}
			| GHSSignalWord = Warning
⚫	}}
			| HPhrases = {{H-phrases|315|319|335}}
⚫	| Section8 = {{Chembox Related
			| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}
	| OtherCpds =
	}}		}}
		⚫	|Section8={{Chembox Related
			| OtherCompounds =
		⚫	}}
	}}		}}
			In ], '''Eschenmoser's salt''' (named for ]) is the ], ] {{chem2|I}}. It is the iodide ] of the dimethylaminomethylene ] {{chem2|+}}.
	'''Eschenmoser's salt''', dimethylmethylideneammonium iodide, is a strong dimethylaminomethylating agent, used to prepare derivatives of the type RCH<sub>2</sub>N(CH<sub>3</sub>)<sub>2</sub>.<ref>E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York.</ref><ref>H. Böhme, E. Mundlos, O.-E.Herboth, "Über Darstellung und Eigenschaften alpha-Halogenierter Amine" '']'' '''1957''', ''90'', 2003-2008.</ref> ]s, ]s, and even more acidic ]s undergo efficient dimethylaminomethylation. Once prepared, such ]s can be further ]ated and then subjected to base-induced ] to afford methylenated ]s. The salt was first prepared by the group of ] after whom the reagent is named.<ref>{{cite journal
⚫	| author = Jakob Schreiber, Hans Maag, Naoto Hashimoto, Albert Eschenmoser
			The dimethylaminomethylene cation is a strong dimethylaminomethylating agent, used to prepare ] of the type {{chem2|RCH2N(CH3)2}}.<ref name=Kleinman>E. F. Kleinman in "Dimethylmethyleneammonium Iodide and Chloride" in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2004, J. Wiley & Sons, New York. {{doi|10.1002/047084289X.rd346}}</ref><ref name=Boehme>{{cite journal
	| title = Dimethyl(methylene)ammonium Iodide
			|author1=Horst Böhme |author2=Eberhard Mundlos |author3=Otto-Erich Herboth | title = Über Darstellung und Eigenschaften α-Halogenierter Amine
			| journal = ]
			| volume = 90
			| issue = 9
			| year = 1957
			| pages = 2003–2008
			| doi = 10.1002/cber.19570900942}}</ref> ]s, ]s, and even more acidic ]s undergo efficient dimethylaminomethylation. Once prepared, such ]s can be further ]ated and then subjected to base-induced ] to afford methylidenated ]s. The salt was first prepared by the group of ]<ref name=EROS>{{cite journal
		⚫	|author1=Jakob Schreiber |author2=Hans Maag |author3=Naoto Hashimoto |author4=Albert Eschenmoser | title = Dimethyl(methylene)ammonium Iodide
	| journal = ]		| journal = ]
	| volume = 10		| volume = 10
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	| year = 1971		| year = 1971
	| pages = 330–331		| pages = 330–331
	| doi = 10.1002/anie.197103301}}</ref>		| doi = 10.1002/anie.197103301}}</ref> after whom the reagent is named.
			==Structure and bonding==
			Dimethylaminomethylene cation is described as a ] of the ] and an ] cation:
			:<chem>(CH3)2N-CH2+ <=> (CH3)2N+=CH2</chem>
			The {{chem2|C3N}} atoms are coplanar. The cation is isoelectronic with ].
			==Preparation==
			Pyrolysis of iodomethyltrimethylammonium iodide affords the desired salt:<ref name=EROS/>
			:<chem>I -> I + CH3I</chem>
			An alternative route starts with bis(dimethylamino)methane:
			:<chem>2CH2 + (CH3)3SiI -> I + (CH3)3SiN(CH3)2</chem>
			==Related salts==
			Other salts of the dimethylaminomethylene cation:
			*Dimethyl(methylidene)ammonium trifluoroacetate.<ref>{{cite journal |doi=10.15227/orgsyn.059.0153|title=Regioselective Mannich Condensation with Dimethyl(Methylene)Ammonium Trifluoroacetate: 1-(Dimethylamino)-4-Methyl-3-Pentanone|journal=Organic Syntheses|year=1979|volume=59|page=153|first1=Michel|last1= Gaudry|first2=Yves|last2=Jasor|first3=Trung Bui|last3=Khac}}</ref>{{r|Kleinman}}
			*Dimethyl(methylidene)ammonium chloride (''Böhme's salt''{{r|Kleinman}}, after ])
			==See also==
			* ], {{chem2|Cl}}.
	==References==		==References==
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