Benzisoxazole

1,2-Benzisoxazole is an aromatic organic compound with a molecular formula C7H5NO containing a benzene-fused isoxazole ring structure.[1][2] The compound itself has no common applications; however, functionalized benzisoxazoles and benzisoxazoyls have a variety of uses, including pharmaceutical drugs such as some antipsychotics (including risperidone, paliperidone, ocaperidone, and iloperidone) and the anticonvulsant zonisamide.Its aromaticity makes it relatively stable;[3] however, it is only weakly basic.Benzisoxazole may be prepared from inexpensive salicylaldehyde, via a base catalyzed room temperature reaction with hydroxylamine-O-sulfonic acid.[4] First reported by Daniel S. Kemp,[5][6][7] the relatively weak N-O bond can be cleaved by a strong base to yield a 2-hydroxybenzonitrile species.
Skeletal formula with numbering convention
Ball-and-stick molecular model
Space-filling molecular model
Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA
Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA
2,1-BenzisoxazolePreferred IUPAC nameCAS NumberBeilstein ReferenceChEMBLChemSpiderECHA InfoCardEC NumberPubChemCompTox DashboardSMILESChemical formulaMolar massDensityBoiling pointGHS labellingPictogramsHazard statementsPrecautionary statementsFlash pointstandard statearomaticorganic compoundbenzeneisoxazolerisperidonepaliperidoneocaperidoneiloperidonezonisamidearomaticitysalicylaldehydehydroxylamine-O-sulfonic acidDaniel S. KempBenzoxazoleAnthranilSimple aromatic ringsBorireneCyclopropenonePyrroleImidazoleThiophenePhospholePyrazoleOxazoleThiazoleIsothiazoleTriazoleTetrazolePentazolePyridinePyrazinePyrimidinePyridazineTriazineTetrazinePentazineHexazineBorepinTroponeAzonineCyclooctadecanonaeneDiazapentaleneThienothiopheneTrithiapentaleneBenzofuranIsobenzofuranIndoleIsoindoleBenzothiopheneBenzo(c)thiopheneBenzophospholeBenzimidazolePurineIndazoleBenzothiazole5-Aza-7-deazapurineNaphthaleneQuinolineIsoquinolineQuinoxalineQuinazolineCinnolinePhthalazineAzulene