| 词条 | Thioanisole |
| 释义 |
| ImageFile = Thioanisol.svg | ImageSize = 128 px | ImageAlt = | PIN = (Methylsulfanyl)benzene[1] | OtherNames = Thioanisole (no longer recommended[1]) Methyl(phenyl)sulfane Phenyl methyl sulfide Methylthiobenzene |Section1={{Chembox Identifiers | CASNo = 100-68-5 | EINECS = 202-878-2 | CASNo_Ref = | PubChem = 7520 | ChemSpiderID = 7239 | SMILES = CSC1=CC=CC=C1 | InChI = 1/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3 | InChIKey = HNKJADCVZUBCPG-UHFFFAOYAJ | StdInChI = 1S/C7H8S/c1-8-7-5-3-2-4-6-7/h2-6H,1H3 | StdInChIKey = HNKJADCVZUBCPG-UHFFFAOYSA-N }} |Section2={{Chembox Properties | C=7|H=8|S=1 | Appearance = colorless liquid | Density = 1.0533 g/cm3 | MeltingPtC = -15 | BoilingPtC = 193 | Solubility = }} |Section3={{Chembox Hazards | MainHazards = | FlashPt = | AutoignitionPt = }} }} Thioanisole is an organic compound with the formula CH3SC6H5. It is a colorless liquid that is soluble in organic solvents. It is the simplest alkyl–aryl thioether. The name indicates that this compound is the sulfur analogue—the thioether rather than the oxygen-centered ether—of anisole. It can be prepared by methylation of thiophenol. ReactionsThioanisole undergoes deprotonation with alkyllithium reagents to afford C6H5SCH2Li, a strong nucleophile that can be alkylated to form more complex chains and structures. The resulting homologated thioether can be manipulated in a variety of ways.[2] Oxidation of sulfur via addition of a single oxygen atom gives the chiral methyl phenyl sulfoxide,[3] a reaction useful for titration of oxidants such as dimethyldioxirane.[4] Successive oxidation then leads to the sulfone. References1. ^1 {{cite book | title = Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book) | publisher = The Royal Society of Chemistry | date = 2014 | location = Cambridge | page = 707 | doi = 10.1039/9781849733069-00648 | isbn = 978-0-85404-182-4}} 2. ^Bailey, Simon "Thioanisole" e-EROS Encyclopedia of Reagents for Organic Synthesis, 2001, John Wiley & Sons. {{DOI|10.1002/047084289X.rt093}} 3. ^{{OrgSynth |first1= Carl R. |last1= Johnson |first2= Jeffrey E. |last2= Keiser |title= Methyl Phenyl Sulfoxide |year= 1966 |volume= 46 |pages= 78 |prep= CV5P0791 |collvol= 5 |collvolpages= 791 }} 4. ^{{cite journal |title= Spectral and chemical properties of dimethyldioxirane as determined by experiment and ab initio calculations |first1= Waldemar |last1= Adam |first2= Yuk Yee |last2= Chan |first3= Dieter |last3= Cremer |first4= Juergen |last4= Gauss |first5= Dieter |last5= Scheutzow |first6= Michael |last6= Schindler |journal= J. Org. Chem. |year= 1987 |volume= 52 |issue= 13 |pages =2800–2803 |doi= 10.1021/jo00389a029 }} 2 : Thioethers|Phenyl compounds |
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