| 词条 | Benzonitrile |
| 释义 |
| Watchedfields = changed | verifiedrevid = 443416795 | ImageFileL1 = Benzonitrile structure.svg | ImageNameL1 = Skeletal formula | ImageFileR1 = Benzonitrile-3D-balls.png | ImageNameR1 = Ball-and-stick model | PIN = Benzonitrile | SystematicName = Benzenecarbonitrile | OtherNames=cyanobenzene phenyl cyanide |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 9V9APP5H5S | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 27991 | SMILES = c1ccc(cc1)C#N | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = C09814 | InChI = 1/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H | PubChem = 7505 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID = 7224 | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 15819 | InChIKey = JFDZBHWFFUWGJE-UHFFFAOYAY | RTECS=DI2450000 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C7H5N/c8-6-7-4-2-1-3-5-7/h1-5H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = JFDZBHWFFUWGJE-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=100-47-0 |Section2={{Chembox Properties | Formula={{chem2|C6H5(CN)}} | MolarMass=103.12 g/mol | Density=1.0 g/ml | MeltingPtC=-13 | BoilingPtC=188 to 191 | Solubility=<0.5 g/100 ml (22 °C) | Solvent=Water | RefractIndex=1.5280 | MagSus = -65.19·10−6 cm3/mol |Section3={{Chembox Hazards | EUClass=Harmful (Xn) | NFPA-H=3 | NFPA-F=2 | NFPA-R=0 | RPhrases={{R21/22}} | SPhrases={{S2}}, {{S23}} | FlashPtC = 75 | AutoignitionPtC = 550 | ExploLimits=1.4–7.2% }} Benzonitrile is the chemical compound with the formula {{chem2|C6H5(CN)}}, abbreviated PhCN. This aromatic organic compound is a colorless liquid with a sweet almond odour. It is mainly used as a precursor to the resin benzoguanamine. ProductionIt is prepared by ammoxidation of toluene, that is its reaction with ammonia and oxygen (or air) at {{convert|400|to|450|C|F}}.[1] {{chem2|C6H5CH3}} + 3/2 {{chem2|O2}} + {{chem2|NH3}} → {{chem2|C6H5(CN)}} + {{chem2|3 H2O}} In the laboratory it can be prepared by the dehydration of benzamide or by the Rosenmund–von Braun reaction using cuprous cyanide or NaCN/DMSO and bromobenzene. ApplicationsLaboratory usesBenzonitrile is a useful solvent and a versatile precursor to many derivatives. It reacts with amines to afford N-substituted benzamides after hydrolysis.[2] It is a precursor to {{chem2|Ph2C=NH}} (b.p. 151 °C, 8 mm Hg) via reaction with phenylmagnesium bromide followed by methanolysis.[3] Benzonitrile forms coordination complexes with transition metals that are both soluble in organic solvents and conveniently labile. One example is {{chem2|PdCl2(PhCN)2}}. The benzonitrile ligands are readily displaced by stronger ligands, making benzonitrile complexes useful synthetic intermediates.[4] HistoryBenzonitrile was reported by Hermann Fehling in 1844. He found the compound as a product from the thermal dehydration of ammonium benzoate. He deduced its structure from the already known analogue reaction of ammonium formate yielding formonitrile. He also coined the name benzonitrile which gave the name to all the group of nitriles.[5] In 2018, benzonitrile was reported to be detected in the interstellar medium.[6] References1. ^{{cite journal |title=Benzoic Acid and Derivatives |journal=Ullmann's Encyclopedia of Industrial Chemistry |first1=Takao |last1=Maki |first2=Kazuo |last2=Takeda |date=June 2000 |doi=10.1002/14356007.a03_555}} 2. ^{{OrgSynth |title=N-Phenylbenzamidine |first1=F. C. |last1=Cooper |first2=M. W. |last2=Partridge |collvol=4 |collvolpages=769 |year=1963 |prep=cv4p0769}} 3. ^{{OrgSynth |title=Diphenyl Ketimine |first1=P. L. |last1=Pickard |first2=T. L. |last2=Tolbert |collvol=5 |collvolpages=520 |year=1973 |prep=cv5p0520}} 4. ^{{cite book |chapter=Bis(Benzonitrile)Dichloro Complexes of Palladium and Platinum |title=Reagents for Transition Metal Complex and Organometallic Syntheses |series=Inorganic Syntheses |publisher=John Wiley & Sons |first1=Gordon K. |last1=Anderson |first2=Minren |last2=Lin |volume=28 |pages=60-63 |date=1990 |doi=10.1002/9780470132593.ch13 |isbn=978-0-470-13259-3}} 5. ^{{cite journal |title=Ueber die Zersetzung des benzoësauren Ammoniaks durch die Wärme |journal=Annalen der Chemie und Pharmacie |first=Hermann |last=Fehling |volume=49 |issue=1 |pages=91–97 |date=1844 |doi=10.1002/jlac.18440490106}} 6. ^{{cite journal |title=Detection of the aromatic molecule benzonitrile ({{chem2|c\\sC6H5CN}}) in the interstellar medium |journal=Science |first1=Brett A. |last1=McGuire |first2=Andrew M. |last2=Burkhardt |first3=Sergei |last3=Kalenskii |first4=Christopher N. |last4=Shingledecker |first5=Anthony J. |last5=Remijan |first6=Eric |last6=Herbst |first7=Michael C. |last7=McCarthy |display-authors=1 |volume=359 |issue=6372 |pages=202-205 |date=January 2018 |doi=10.1126/science.aao4890 |bibcode=2018Sci...359..202M |arxiv=1801.04228}} External links
3 : Nitriles|Aromatic solvents|Phenyl compounds |
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