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- W4256036144 abstract "[873-67-6] C7H5NO (MW 119.12) InChI = 1S/C7H5NO/c9-8-6-7-4-2-1-3-5-7/h1-5H InChIKey = QUNPTMGXSSDZHZ-UHFFFAOYSA-N (versatile reagent for regio- and stereoselective construction of heterocycles; synthesis of polyfunctionalized acyclic and cyclic compounds1) Physical Data: mp 18–19 °C; bp 113 °C/15 mmHg; d224 1.10 g cm−3; n22D 1.6172. Solubility: sol ether, benzene, CCl4. Form Supplied in: prepared as described below; not commercially available. Preparative Methods: the most widely employed methods of benzonitrile oxide 1 generation involve triethylamine-mediated dehydrohalogenation of benzhydroxamoyl chloride 2 (or bromide), readily accessible through chlorination of benzaldoxime,2a or dehydration of α-nitrotoluene with PhCNO2b,2c or PhSO2Cl or ClCO2Et and a catalytic amount of Et3N (Mukaiyama reaction).2d A reaction of 2 with alkali metal fluorides also provides a facile quantitative generation of 1.2e Although 1 has been obtained as a crystalline solid,2f it is commonly generated in situ.1 Et3N almost immediately reacts with 2,3 and should be added very slowly to an ice-cooled solution of 2to maintain a low stationary concentration of 1 and thereby suppress its dimerization into 3,4-diphenylfuroxan 3.2a Benzonitrile oxide can also be generated photochemically by irradiation of 2 and Hexabutyldistannane,4a or via electrochemical oxidation of benzaldoxime.4b Handling, Storage, and Precautions: usually prepared in situ; readily undergoes dimerization on storage; use in a fume hood." @default.
- W4256036144 created "2022-05-12" @default.
- W4256036144 creator A5024961412 @default.
- W4256036144 date "2001-04-15" @default.
- W4256036144 modified "2023-09-25" @default.
- W4256036144 title "Benzonitrile Oxide" @default.
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- W4256036144 doi "https://doi.org/10.1002/047084289x.rb030" @default.
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