Anthranil

{{distinguish|1,2-Benzisoxazole}}

{{Chembox

| ImageFile = Anthranil.svg

| ImageSize =

| ImageAlt =

| PIN = 2,1-Benzoxazole

| OtherNames =

| Section1 = {{Chembox Identifiers

| CASNo = 271-58-9

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

| Beilstein = 2222

| ChEBI = 51555

| ChEMBL = 508432

| ChemSpiderID = 60822

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

| UNII = 58GQ20G9W6

| PubChem = 67498

| EC_number = 205-980-5

| SMILES = n1c2ccccc2co1

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

| StdInChIKey =FZKCAHQKNJXICB-UHFFFAOYSA-N

}}

| Section2 = {{Chembox Properties

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

| MolarMass =

| Appearance = Colorless liquid

| Density = 1.183 g/mL

| MeltingPt =

| BoilingPtC = 101 - 102

| BoilingPt_ref =

| Solubility =

}}

| Section3 = {{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

| GHSPictograms = {{GHS07}}{{Sigma-Aldrich|id=144517|name=Anthranil|accessdate=2017-03-02}}

| GHSSignalWord = Warning

| HPhrases = {{H-phrases|302}}

| PPhrases = {{P-phrases|264|270|301+312|330|501}}

}}

}}

Anthranil (2,1-benzisoxazole) is an organic compound with a molecular formula C7H5NO, which features a fused benzene-isoxazole bicyclic ring structure. It is an isomer of the more common compounds benzoxazole and benzisoxazole, which have their oxygen atoms located in the 1-position. The locations of the heteroatoms in anthranil results in disrupted aromaticity, making it by far the least stable of the 3 structural isomers.{{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}}

References