| 词条 | Methyl isocyanide |
| 释义 |
| Watchedfields = changed | verifiedrevid = 455280169 | ImageFile1 = Methyl isocyanide.svg | ImageSize1 = 180px | ImageFile2 = Methyl-isocyanide-3D-balls.png | ImageSize2 = 150px | IUPACName = Isocyanomethane | OtherNames = {{ubl|Methyl isocyanide| Isoacetonitrile| Methylisonitrile| Isomethanenitrile| Methaneisonitrile}} |Section1={{Chembox Identifiers | Abbreviations = | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 11156 | InChI = 1/C2H3N/c1-3-2/h1H3 | InChIKey = ZRKSVHFXTRFQFL-UHFFFAOYAI | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C2H3N/c1-3-2/h1H3 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = ZRKSVHFXTRFQFL-UHFFFAOYSA-N | CASNo = 593-75-9 | CASNo_Ref = {{cascite|correct|CAS}} | EINECS = | PubChem = 11646 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = DB04337 | SMILES = [C-]#[N+]C | RTECS = | MeSHName = | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 44177 | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = }} |Section2={{Chembox Properties | H=3 | N=1 | C=2 | Appearance = Colorless liquid | Density = 0.69 g/mL | MeltingPtC = −45 | MeltingPt_notes = | BoilingPtC = 59 to 60 | BoilingPt_notes = | Solubility = Miscible | SolubleOther = | Solvent = | pKb = |Section7={{Chembox Hazards | EUClass = Flammable, harmful | MainHazards = | NFPA-H = 2 | NFPA-F = 3 | NFPA-R = 0 | NFPA-S = | RPhrases = {{R11}}, {{R20/21/22}}, {{R36}} | SPhrases = {{(S1/2)}}, {{S16}}, {{S36/37}} | RSPhrases = | AutoignitionPt = | ExploLimits = | PEL = |Section8={{Chembox Related | OtherAnions = | OtherCations = | OtherFunction = | OtherFunction_label = | OtherCompounds = acetic acid, acetamide, ethylamine, Acetonitrile}} }} Methyl isocyanide or isocyanomethane is an organic compound and a member of the isocyanide family. This colorless liquid is isomeric to methyl cyanide (acetonitrile), but its reactivity is very different. Methyl isocyanide is mainly used for making 5-membered heterocyclic rings. The C-N distance in methyl isocyanide is very short, 1.158 Å as is characteristic of isocyanides. [1]Preparation and usesMethyl isocyanide was first prepared Gautier by reaction of silver cyanide with methyl iodide.[2][3] The common method for preparing methyl isocyanides is the dehydration of N-methylformamide.[4] Methyl isocyanide is useful for the preparation of diverse heterocycles. It is also a ligand in organometallic chemistry.[5] References1. ^Myer Kessler, Harold Ring, Ralph Trambarulo, Walter Gordy "Microwave Spectra and Molecular Structures of Methyl Cyanide and Methyl Isocyanide" Phys. Rev. 1950, vol. 79, 54–56. {{DOI:10.1103/PhysRev.79.54}} 2. ^{{cite journal | author = Gautier, A. | title = Ueber eine neue Reihe von Verbindungen, welche mit den Cyanwasserstoffsäure-Aethern isomer sind | journal = Justus Liebigs Annalen der Chemie | year = 1868 | volume = 146 | issue = 1 | pages = 119–124 | doi = 10.1002/jlac.18681460107 }} 3. ^{{cite journal | author = Gautier, A. | title = Des Nitriles des Acides Gras: Deuxième Partie - Des Carbylamines | journal = Annales de Chimie et de Physique | year = 1869 | volume = 17 | page = 203 | url = http://gallica.bnf.fr/ark:/12148/bpt6k34827s/f102.image.langEN }} 4. ^{{OrgSynth | author = R. E. Schuster, James E. Scott, and Joseph Casanova, Jr | title = Methyl isocyanide | year = 1966 | volume = 46 | pages = 75 | DOI = 10.15227/orgsyn.046.0075 }} 5. ^{{ cite encyclopedia |author1=Eckert, H. |author2=Nestl, A. |author3=Ugi, I. | title = Methyl isocyanide | encyclopedia = Encyclopedia of Reagents for Organic Synthesis | year = 2001 | publisher = John Wiley & Sons | doi = 10.1002/047084289X.rm198 }} External links
3 : Hazardous air pollutants|Isocyanides|Ligands |
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