| 词条 | Methyl vinyl ether |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 446462381 | Name = | ImageFile = Methylvinylether.png | ImageSize = 112px | ImageAlt = | ImageName = | PIN = Methoxyethene | SystematicName = | OtherNames = Ethenyl methyl ether Vinyl methyl ether |Section1={{Chembox Identifiers | 3DMet = | Abbreviations = | Beilstein = | CASNo = 107-25-5 | CASNo_Ref = {{cascite|correct|CAS}}= | CASNoOther = | UNII_Ref = {{fdacite|changed|FDA}} | UNII = G2OHX46576 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7573 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | EC_number = | EINECS = | Gmelin = | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C3H6O/c1-3-4-2/h3H,1H2,2H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = XJRBAMWJDBPFIM-UHFFFAOYSA-N | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = | MeSHName = | PubChem = 7861 | RTECS = | SMILES = O(C=C)C | SMILES1 = COC=C | UNNumber = }} |Section2={{Chembox Properties | AtmosphericOHRateConstant = | Appearance = | BoilingPtC = 6 | BoilingPt_ref = [1] | BoilingPt_notes = | Density = 0.77 g/cm−3[1] | C=3 | H=6 | O=1 | HenryConstant = | LogP = | MeltingPtC = −122 | MeltingPt_ref = [1] | MeltingPt_notes = | pKa = | pKb = | Solubility = | SolubleOther = | Solvent = | VaporPressure = 157 kPa (20 °C)[1] }} |Section3={{Chembox Structure | Coordination = | CrystalStruct = | MolShape = }} |Section4={{Chembox Thermochemistry | DeltaHc = | DeltaHf = | Entropy = | HeatCapacity = }} |Section7={{Chembox Hazards | ExternalSDS = | EUClass = {{Hazchem F+}} | MainHazards = | NFPA-H = | NFPA-F = | NFPA-R = | NFPA-S = | RPhrases = {{R12}} | SPhrases = {{(S2)}}, {{S9}}, {{S16}}, {{S33}} | RSPhrases = | FlashPtC = −60 | AutoignitionPtC = | ExploLimits = | LD50 = | PEL = }} |Section8={{Chembox Related | OtherFunction_label = | OtherAnions = | OtherCations = | OtherCompounds = | OtherFunction = }} Methyl vinyl ether is an organic compound with the chemical formula CH3OCH=CH2. A colorless gas, it is the simplest enol ether. Together with ethyl vinyl ether (a liquid at room temperature), it is used as a synthetic building block. PreparationMethyl vinyl ether can be made by reaction of acetylene and methanol in presence of a base.[2][3] ReactionsThe alkene portion of the molecule is reactive in many ways. It is prone to polymerization, leading to formation of polyvinyl ethers. Polymerization is typically initiated with Lewis acids such as boron trifluoride.[4] This mode of reactivity is analogous to the way vinyl acetate and vinyl chloride can be polymerized to form polyvinyl acetate and polyvinyl chloride, respectively. Methyl vinyl ether also participates in [4+2] cycloaddition reactions.[5] The reaction of it with acrolein is the first step in the commercial synthesis of glutaraldehyde. The alkene can be deprotonated adjacent to the oxygen attachment.[6] 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.[7][8][9] ToxicityThe toxicity of vinyl ethers has been heavily investigated because divinyl ether has been used as an anesthetic. The acute LD50 for methyl vinyl ether is greater than 4 g/kg (rats, oral).[3] References1. ^1 2 3 {{GESTIS|Name=Methylvinylether|ZVG=29130|CAS=107-25-5 |Date=20 April 2008}} 2. ^{{cite journal|title=Oxygenated fuel additives: The formation of methyl vinyl ether and 1,1-dimethoxyethane by the catalysed reaction of acetylene with methanol|authors=David Trimma, Noel Cant, Yun Lei|journal=Catalysis Today|volume=145|year= 2009|pages=163–168 |doi=10.1016/j.cattod.2008.04.015}} 3. ^1 {{cite encyclopedia|title=Vinyl Ethers|authors=Ernst Hofmann, Hans‐Joachim Klimisch, René Backes, Regina Vogelsang, Lothar Franz, Robert Feuerhake|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2011|publisher= Wiley-VCH|doi=10.1002/14356007.a27_435.pub}} 4. ^{{cite encyclopedia|title=Poly(Vinyl Ethers)|authors=Gerd Schröder|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2012|publisher= Wiley-VCH|doi=10.1002/14356007.a22_011}} 5. ^{{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 }} 6. ^{{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 }} 7. ^{{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 |pages= 1577–1583 |doi= 10.1021/ja00525a019 }} 8. ^{{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 |pages= 541–543 |doi= 10.1021/jo01291a041 }} 9. ^{{cite journal |journal=Org. Synth.|author= Soderquist, J. A. |year= 1990 |title= Acetyltrimethylsilane |volume= 68 |pages= 25|doi=10.15227/orgsyn.068.0025 }} 2 : Ethers|Vinyl compounds |
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