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Revision as of 11:07, 10 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers for the Chem/Drugbox validation project (updated: 'ChEMBL', 'ChEBI', 'StdInChI', 'StdInChIKey', 'CASNo').← Previous edit Latest revision as of 01:24, 2 May 2022 edit undoReba16 (talk | contribs)Extended confirmed users8,067 editsNo edit summary 
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{{distinguish|2,1-Benzisoxazole}}
{{Unreferenced|date=December 2009}}
{{Chembox {{Chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 459952251
| ImageFile = 1,2-benzisoxazole numbering.svg | ImageFile = 1,2-benzisoxazole numbering.svg
| ImageSize = | ImageSize = 160
| ImageAlt = Skeletal formula with numbering convention
| IUPACName = 1,2-Benzisoxazole
| OtherNames = 2,1-Benzisoxazole, Anthranil, Benzoisoxazole, Benzisoxazole | ImageFileL2 = Benzisoxazole 3D ball inverted.png
| ImageAltL2 = Ball-and-stick molecular model
⚫ | Section1 = {{Chembox Identifiers
| ImageFileR2 = Benzisoxazole 3D spacefill inverted.png
⚫ | ChemSpiderID = 64227
| ImageAltR2 = Space-filling molecular model
| PIN = 1,2-Benzoxazole
| OtherNames = Benzoisoxazole; Indoxazine
⚫ | Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
⚫ | ChemSpiderID = 64227
| InChIKey = KTZQTRPPVKQPFO-UHFFFAOYAI | InChIKey = KTZQTRPPVKQPFO-UHFFFAOYAI
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 271-58-9 -->
| EINECS = 205-980-5 | CASNo = 271-95-4

⚫ | ChEMBL = 314871
| 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 | 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 | 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 | StdInChIKey = KTZQTRPPVKQPFO-UHFFFAOYSA-N
| PubChem = 67498 | PubChem = 71073
| SMILES = n2oc1ccccc1c2 | SMILES = n2oc1ccccc1c2
| InChI = 1/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H | InChI = 1/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
|C=7|H=5|N=1|O=1 | C=7 | H=5 | N=1 | O=1
| Appearance = Colorless liquid | Appearance = Colorless liquid
| Density = 1.18 g/cm<sup>3</sup> | Density = 1.18 g/cm<sup>3</sup>
| MeltingPt = | MeltingPt =
| BoilingPt = 35 - 38 °C (2.67 hPa)<br> | BoilingPtC = 35 to 38
101 - 102 °C (2 kPa) | BoilingPt_notes = (at 2.67 hPa)<br>101-102 °C (at 2 kPa)
| Solubility = | Solubility =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = 58 °C | FlashPtC = 58
| Autoignition = | AutoignitionPtC =
| GHSPictograms = {{GHS07}}
| SPhrases = {{S24/25}}, {{S28}}A, {{S37}}, {{S45}}
| 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}}
}} }}
}} }}


'''Benzisoxazole''' is an ] ] with a molecular formula C<sub>7</sub>H<sub>5</sub>NO containing a ]-fused ] ring structure. Benzisoxazole has no household use. It is used primarily in industry and research. '''1,2-Benzisoxazole''' is an ] ] with a molecular formula C<sub>7</sub>H<sub>5</sub>NO containing a ]-fused ] ring structure.<ref name="Katritzky2nd">{{Katritzky2nd}}</ref><ref name="Clayden1st">{{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 }}</ref> 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 ], ], ], and ]) and the anticonvulsant ].


Its ] makes it relatively stable;<ref name="DomeneJenneskens2005">{{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}}</ref> however, it is only weakly basic.
Being a ] compound, benzisoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. It is found within the chemical structures of pharmaceutical drugs such as the antipsychotic ] and the anticonvulsant ].


==Synthesis==
Its ] makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.
Benzisoxazole may be prepared from inexpensive ], via a base catalyzed room temperature reaction with ].<ref name="KempWoodward1965">{{cite journal|last1=Kemp|first1=D.S.|last2=Woodward|first2=R.B.|title=The N-ethylbenzisoxazolium cation—I|journal=Tetrahedron|volume=21|issue=11|year=1965|pages=3019–3035|issn=0040-4020|doi=10.1016/S0040-4020(01)96921-2}}</ref>

:]

==Reactions==
===Kemp elimination===
First reported by ],<ref>{{cite journal |last1=Casey |first1=Martha L. |last2=Kemp |first2=D. S. |last3=Paul |first3=Kenneth G. |last4=Cox |first4=Daniel D. |title=Physical organic chemistry of benzisoxazoles. I. Mechanism of the base-catalyzed decomposition of benzisoxazoles |journal=The Journal of Organic Chemistry |date=June 1973 |volume=38 |issue=13 |pages=2294–2301 |doi=10.1021/jo00953a006}}</ref><ref>{{cite journal |last1=Kemp |first1=D. S. |last2=Cox |first2=Daniel D. |last3=Paul |first3=Kenneth G. |title=Physical organic chemistry of benzisoxazoles. IV. Origins and catalytic nature of the solvent rate acceleration for the decarboxylation of 3-carboxybenzisoxazoles |journal=Journal of the American Chemical Society |date=December 1975 |volume=97 |issue=25 |pages=7312–7318 |doi=10.1021/ja00858a018}}</ref><ref>{{cite journal |last1=Kemp |first1=Daniel S. |title=Decarboxylation of benzisoxazole-3-carboxylic acids. Catalysis by extraction of possible relevance to the problem of enzymic mechanism |journal=Journal of the American Chemical Society |date=April 1970 |volume=92 |issue=8 |pages=2553–2554 |doi=10.1021/ja00711a061}}</ref> the relatively weak N-O bond can be cleaved by a strong base to yield a 2-hydroxybenzonitrile species.

]


==See also== ==See also==
;Structural isomers
*]
*] *]
*]


== References ==
⚫ ]
{{reflist}}
⚫ ]


{{Simple aromatic rings}}
]

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