Benzisoxazole

{{distinguish|2,1-Benzisoxazole}}

{{Chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 459952251

| ImageFile = 1,2-benzisoxazole numbering.svg

| ImageSize = 160

| ImageAlt = Skeletal formula with numbering convention

| ImageFileL2 = Benzisoxazole 3D ball inverted.png

| ImageAltL2 = Ball-and-stick molecular model

| ImageFileR2 = Benzisoxazole 3D spacefill inverted.png

| ImageAltR2 = Space-filling molecular model

| PIN = 1,2-Benzoxazole

| OtherNames = Benzo[d]isoxazole; Indoxazine

| Section1={{Chembox Identifiers

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 64227

| InChIKey = KTZQTRPPVKQPFO-UHFFFAOYAI

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 271-95-4

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = D879RKM5NQ

| EINECS = 205-983-1

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 314871

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 51554

| Beilstein = 2154

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = KTZQTRPPVKQPFO-UHFFFAOYSA-N

| PubChem = 71073

| SMILES = n2oc1ccccc1c2

| InChI = 1/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H

}}

|Section2={{Chembox Properties

| C=7 | H=5 | N=1 | O=1

| Appearance = Colorless liquid

| Density = 1.18 g/cm³

| MeltingPt =

| BoilingPtC = 35 to 38

| BoilingPt_notes = (at 2.67 hPa)
101-102 °C (at 2 kPa)

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPtC = 58

| AutoignitionPtC =

| GHSPictograms = {{GHS07}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|315|319|335}}

| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}}

}}

}}

1,2-Benzisoxazole is an aromatic organic compound with a molecular formula C₇H₅NO containing a benzene-fused isoxazole ring structure.{{Katritzky2nd}}{{cite book |last=Clayden |first=J. |last2=Greeves |first2=N. |last3=Warren |first3=S. |last4=Wothers |first4=P. |title=Organic Chemistry |publisher=Oxford University Press |location=Oxford, Oxfordshire |year=2001 |isbn=0-19-850346-6 |url=https://archive.org/details/organicchemistry00clay_0 |url-access=registration }} 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;{{cite journal|last1=Domene|first1=Carmen|last2=Jenneskens|first2=Leonardus W.|last3=Fowler|first3=Patrick W.|title=Aromaticity of anthranil and its isomers, 1,2-benzisoxazole and benzoxazole|journal=Tetrahedron Letters|volume=46|issue=23|year=2005|pages=4077–4080|issn=0040-4039|doi=10.1016/j.tetlet.2005.04.014|hdl=1874/14837|hdl-access=free}} however, it is only weakly basic.