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Revision as of 09:41, 24 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (changes to watched fields - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report ← Previous edit		Latest revision as of 18:01, 25 September 2023 edit undoAnomieBOT (talk | contribs)Bots6,551,003 editsm Substing templates: {{Format ISBN}}. See User:AnomieBOT/docs/TemplateSubster for info.
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	{{Chembox		{{Chembox
			| Verifiedfields = changed
	| Watchedfields = changed		| Watchedfields = changed
	| verifiedrevid = 426633785		| verifiedrevid = 446462381
	| Name =		| Name =
	| ImageFile = Methylvinylether.png		| ImageFile = Methylvinylether.png
	| ImageSize = 112px		| ImageSize = 112px
	| ImageAlt =		| ImageAlt =
	| ImageName =		| ImageName =
			| PIN = Methoxyethene
	| IUPACName =
	| SystematicName =		| SystematicName =
	| OtherNames = Methoxyethene, ethenyl methyl ether, vinyl methyl ether		| OtherNames = Ethenyl methyl ether<br />Vinyl methyl ether
	| Section1 = {{Chembox Identifiers		|Section1={{Chembox Identifiers
	| 3DMet =		| 3DMet =
	| Abbreviations =		| Abbreviations =
	| ATCvet =		| Beilstein =
			| CASNo = 107-25-5
	| ATCCode_prefix =
		⚫	| CASNo_Ref = {{cascite|correct|CAS}}
	| ATCCode_suffix =
			| EC_number = 203-475-4
	| ATC_Supplemental =
			| UNII_Ref = {{fdacite|changed|FDA}}
	| Beilstein =
	| CASNo = 107-25-5		| UNII = G2OHX46576
		⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| CASNo_Ref =
	| CASNos =
	| CASOther =
⚫	| ChEBI_Ref = {{ebicite|correct|EBI}}
	| ChEBI =		| ChEBI =
	| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}		| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
	| ChemSpiderID = 7573		| ChemSpiderID = 7573
		⚫	| UNNumber = 1087
	| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
		⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| DrugBank =
	| EC-number =
⚫	| EINECS =
	| EINECSCASNO =
	| Gmelin =
⚫	| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChI = 1S/C3H6O/c1-3-4-2/h3H,1H2,2H3		| StdInChI = 1S/C3H6O/c1-3-4-2/h3H,1H2,2H3
	| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}		| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
	| StdInChIKey = XJRBAMWJDBPFIM-UHFFFAOYSA-N		| StdInChIKey = XJRBAMWJDBPFIM-UHFFFAOYSA-N
		⚫	| PubChem = 7861
⚫	| KEGG_Ref = {{keggcite|correct|kegg}}
	| KEGG =		| SMILES = O(C=C)C
	| MeSHName =		| SMILES1 = COC=C
⚫	| PubChem = 7861
⚫	| RTECS =
	| SMILES = O(C=C)C
	| SMILES1 = COC=C
⚫	| UNNumber =
	}}		}}
	| Section2 = {{Chembox Properties		|Section2={{Chembox Properties
	| AtmosphericOHRateConstant =		| AtmosphericOHRateConstant =
	| Appearance =		| Appearance =
			| BoilingPtC = 6
	| BoilingPt = 6&nbsp;°C<ref name="GESTIS">{{GESTIS|Name=Methylvinylether|ZVG=29130|CAS=107-25-5 |Datum=20.4.2008}}</ref>		| BoilingPt_ref = <ref name="GESTIS">{{GESTIS|Name=Methylvinylether|ZVG=29130|CAS=107-25-5 |Date=20 April 2008}}</ref>
	| Boiling_notes =
			| BoilingPt_notes =
	| Density = 0.77&nbsp;g/cm<sup>–3</sup><ref name="GESTIS"/>		| Density = 0.77&nbsp;g/cm<sup>−3</sup><ref name="GESTIS"/>
	| C=3 | H=6 | O=1
	| HenryConstant =		| C=3 | H=6 | O=1
	| LogP =		| HenryConstant =
		⚫	| LogP =
⚫	| MeltingPt = –122&nbsp;°C<ref name="GESTIS"/>
			| MeltingPtC = −122
	| Melting_notes =
			| MeltingPt_ref = <ref name="GESTIS"/>
⚫	| pKa =
			| MeltingPt_notes =
	| pKb =
	| Solubility =		| pKa =
	| SolubleOther =		| pKb =
	| Solvent =		| Solubility =
			| SolubleOther =
	| VaporPressure = 157&nbsp;kPa (20&nbsp;°C)<ref name="GESTIS"/> }}
		⚫	| Solvent =
⚫	| Section3 = {{Chembox Structure
		⚫	| VaporPressure = 157&nbsp;kPa (20&nbsp;°C)<ref name="GESTIS"/> }}
	| Coordination =
		⚫	|Section3={{Chembox Structure
⚫	| CrystalStruct =
	| MolShape = }}		| Coordination =
		⚫	| CrystalStruct =
⚫	| Section4 = {{Chembox Thermochemistry
	| DeltaHc =		| MolShape = }}
		⚫	|Section4={{Chembox Thermochemistry
	| DeltaHf =
	| Entropy =		| DeltaHc =
	| HeatCapacity = }}		| DeltaHf =
			| Entropy =
⚫	| Section7 = {{Chembox Hazards
	| ExternalMSDS =		| HeatCapacity = }}
		⚫	|Section7={{Chembox Hazards
	| EUClass = {{Hazchem F+}}
	| EUIndex =		| ExternalSDS =
	| MainHazards =		| MainHazards =
	| NFPA-H =		| NFPA-H = 2
	| NFPA-F =		| NFPA-F = 4
	| NFPA-R =		| NFPA-R = 2
	| NFPA-O =		| NFPA-S = W
	| RPhrases = {{R12}}		| GHSPictograms = {{GHS02}}
			| GHSSignalWord = Danger
	| SPhrases = {{(S2)}}, {{S9}}, {{S16}}, {{S33}}
			| HPhrases = {{H-phrases|220}}
	| RSPhrases =
			| PPhrases = {{P-phrases|210|377|381|403}}
	| FlashPt = –60&nbsp;°C
	| Autoignition =		| FlashPtC = −60
	| ExploLimits =		| AutoignitionPtC =
	| LD50 =		| ExploLimits =
	| PEL = }}		| LD50 =
		⚫	| PEL = }}
	| Section8 = {{Chembox Related		|Section8={{Chembox Related
	| Function =
	| OtherAnions =		| OtherFunction_label =
	| OtherCations =		| OtherAnions =
	| OtherCpds =		| OtherCations =
			| OtherCompounds =
	| OtherFunctn = }}
			| OtherFunction =
			}}
	}}		}}
	'''Methyl vinyl ether''' is an organic compound with the chemical formula C<sub>3</sub>H<sub>6</sub>O. It is the simplest chemical that contains both an ] group and an ] group with an ] linkage. The compound can be made by reaction of ] and ] in presence of a base. <ref>''Oxygenated fuel additives: The formation of methyl vinyl ether and 1,1-dimethoxyethane by the catalysed reaction of acetylene with methanol'' David Trimma, Corresponding Author Contact Information, E-mail The Corresponding Author, Noel Cantb and Yun Leib Catalysis Today Volume 145, Issues 1-2, 15 July 2009, Pages 163-168 {{DOI|10.1016/j.cattod.2008.04.015}} </ref>		'''Methyl vinyl ether''' is an ] with the chemical formula CH<sub>3</sub>OCH=CH<sub>2</sub>. A colorless gas, it is the simplest ]. It is used as a synthetic building block, as is the related compound ] (a liquid at room temperature).
			==Preparation==
⚫	The alkene portion of the molecule is reactive in many ways. It is prone to ], leading to formation of poly(methyl vinyl ether) (PMVE, ]: 9003-09-2). This mode of reactivity is analogous to the way ] and ] can be polymerized to form ] and ], respectively. The alkene can also react in ] reactions.<ref name=longly>{{cite journal |title= The 1,4-Addition of Vinyl Ethers to α,β-Unsaturated Carbonyl Compounds |authors= Longley, Jr., R. I.; Emerson, W. S. |journal= J. Am. Chem. Soc. |year= 1950 |volume= 72 |issue= 7 |pages= 3079–3081 |doi= 10.1021/ja01163a076 }}</ref> The reaction of it with ] is the first step in the commercial synthesis of ].
			Methyl vinyl ether can be made by reaction of ] and ] in presence of a base.<ref>{{cite journal|title=Oxygenated fuel additives: The formation of methyl vinyl ether and 1,1-dimethoxyethane by the catalysed reaction of acetylene with methanol|author=David Trimma |author2=Noel Cant |author3=Yun Lei |journal=Catalysis Today|volume=145|issue=1–2|year= 2009|pages=163–168 |doi=10.1016/j.cattod.2008.04.015}}</ref><ref name=Ullm>{{cite encyclopedia|chapter=Vinyl Ethers|author=Ernst Hofmann |author2=Hans‐Joachim Klimisch |author3=René Backes |author4=Regina Vogelsang |author5=Lothar Franz |author6=Robert Feuerhake |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2011|publisher= Wiley-VCH|doi=10.1002/14356007.a27_435.pub2|isbn=978-3-527-30673-2}}</ref>
			==Reactions==
⚫	The compound is useful as a ] for ] ], via deprotonation of the alkene adjacent to the oxygen attachment.<ref name=lever>{{cite journal |title= New horizons in carbonyl chemistry: reagents for nucleophilic acylation |author= Lever, Jr., O. W. |journal= Tetrahedron |year= 1976 |volume= 32 |pages= 1943–1971 |doi= 10.1016/0040-4020(76)80088-9 }}</ref> In particular, this approach allows synthesis of a variety of acyl derivatives of silicon, germanium, and tin that cannot be made easily by other routes<ref name=soderguistJACS>{{cite journal |title= Synthetic methods. 15. Unsaturated acyl derivatives of silicon, germanium, and tin from metalated enol ethers |author= Soderquist, J. A.; Hassner, A. |journal= J. Am. Chem. Soc. |year= 1980 |volume= 102 |pages= 1577–1583 |doi= 10.1021/ja00525a019 }}</ref><ref name=soderguistJOC>{{cite journal |author= Soderquist, J. A.; Hassner, A. |title= Vinylmetalloids. 3. Sila- and germacyclopentan-2-ones from metallated enol ethers |journal= J. Org. Chem. |year= 1980 |volume= 45 |pages= 541–543 |doi= 10.1021/jo01291a041 }}</ref><ref name=orgsyn8.19>{{OrgSynth |author= Soderquist, J. A. |year= 1990 |title= Acetyltrimethylsilane |volume= 68 |pages= 25 |collvol= 8 |collvolpages= 19 |prep= cv8p0019 }}</ref>
			The alkene portion of the molecule is reactive in many ways. It is prone to ], leading to formation of ]s. Polymerization is typically initiated with ]s such as ].<ref>{{cite encyclopedia|chapter=Poly(Vinyl Ethers)|author=Gerd Schröder |encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2012|publisher= Wiley-VCH|doi=10.1002/14356007.a22_011|isbn=978-3-527-30673-2}}</ref> This mode of reactivity is analogous to the way ] and ] can be polymerized to form ] and ], respectively.
		⚫	Methyl vinyl ether also participates in ] reactions.<ref name=longly>{{cite journal |title= The 1,4-Addition of Vinyl Ethers to α,β-Unsaturated Carbonyl Compounds |author= Longley Jr., R. I. |author2= Emerson, W. S. |journal= J. Am. Chem. Soc. |year= 1950 |volume= 72 |issue= 7 |pages= 3079–3081 |doi= 10.1021/ja01163a076 }}</ref> Its reaction with ] is the first step in the commercial synthesis of ].
		⚫	The alkene can be deprotonated at the vinyl carbon adjacent to the oxygen.<ref name=lever>{{cite journal |title= New horizons in carbonyl chemistry: reagents for nucleophilic acylation |author= Lever Jr., O. W. |journal= Tetrahedron |year= 1976 |volume= 32 |issue= 16 |pages= 1943–1971 |doi= 10.1016/0040-4020(76)80088-9 }}</ref> In particular, this approach allows the synthesis of a variety of acyl derivatives of silicon, germanium, and tin that cannot be made easily by other routes.<ref name=soderguistJACS>{{cite journal |title= Synthetic methods. 15. Unsaturated acyl derivatives of silicon, germanium, and tin from metalated enol ethers |author1=Soderquist, J. A. |author2=Hassner, A. |journal= J. Am. Chem. Soc. |year= 1980 |volume= 102 |issue=5 |pages= 1577–1583 |doi= 10.1021/ja00525a019 }}</ref><ref name=soderguistJOC>{{cite journal |author1=Soderquist, J. A. |author2=Hassner, A. |title= Vinylmetalloids. 3. Sila- and germacyclopentan-2-ones from metallated enol ethers |journal= J. Org. Chem. |year= 1980 |volume= 45 |issue=3 |pages= 541–543 |doi= 10.1021/jo01291a041 }}</ref><ref name=orgsyn8.19>{{cite journal |journal=Org. Synth.|author= Soderquist, J. A. |year= 1990 |title= Acetyltrimethylsilane |volume= 68 |page= 25|doi=10.15227/orgsyn.068.0025 }}</ref>
			==Toxicity==
			The toxicity of vinyl ethers has been heavily investigated because ] has been used as an ]. The acute ] for methyl vinyl ether is greater than 4 g/kg (rats, oral).<ref name=Ullm/>
	== References ==		== References ==
	{{reflist}}		{{reflist}}
	{{organic-compound-stub}}
	]		]
	]		]
	]
	]