Benzisoxazole

| Ball-and-stick molecular model | Space-filling molecular model

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Names
Preferred IUPAC name

1,2-Benzoxazole

Other names

Benzo[d]isoxazole; Indoxazine

Identifiers

CAS Number

* 271-95-4 Y

3D model (JSmol)

* Interactive image

Beilstein Reference

| 2154
ChEBI |

* CHEBI:51554 Y

ChEMBL |

* ChEMBL314871 N

ChemSpider |

* 64227 Y

EC Number |

* 205-983-1

PubChem CID

* 71073

UNII |

* D879RKM5NQ Y

InChI

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

Key: KTZQTRPPVKQPFO-UHFFFAOYSA-N Y

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

Key: KTZQTRPPVKQPFO-UHFFFAOYAI

SMILES

* n2oc1ccccc1c2

Properties

Chemical formula

| C7H5NO
Molar mass | 119.123 g·mol−1
Appearance  | Colorless liquid
Density | 1.18 g/cm3
Boiling point |  35 to 38 °C (95 to 100 °F; 308 to 311 K) (at 2.67 hPa)
101-102 °C (at 2 kPa)
Hazards
GHS pictograms |
GHS Signal word | Warning

GHS hazard statements

| H315, H319, H335

GHS precautionary statements

| P261, P264, P271, P280, P302+352, P304+340, P305+351+338, P312, P321, P332+313, P337+313, P362, P403+233, P405, P501
Flash point |  58 °C (136 °F; 331 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

N verify (what is YN ?)
Infobox references

Tracking categories (test):

* SizeSet

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.

## Contents

* 1 Synthesis
* 2 Reactions
* 2.1 Kemp elimination
* 3 See also
* 4 References

## Synthesis

Benzisoxazole may be prepared from inexpensive salicylaldehyde, via a base catalyzed room temperature reaction with hydroxylamine-O-sulfonic acid.[4]

Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA

## Reactions

### Kemp elimination

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.

## See also

Structural isomers

* Benzoxazole
* Anthranil

## References

1. ↑ Template:Katritzky2nd
2. ↑ Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6. https://archive.org/details/organicchemistry00clay_0.
3. ↑ Domene, Carmen; Jenneskens, Leonardus W.; Fowler, Patrick W. (2005). "Aromaticity of anthranil and its isomers, 1,2-benzisoxazole and benzoxazole". Tetrahedron Letters 46 (23): 4077–4080. doi:10.1016/j.tetlet.2005.04.014. ISSN 0040-4039.
4. ↑ Kemp, D.S.; Woodward, R.B. (1965). "The N-ethylbenzisoxazolium cation—I". Tetrahedron 21 (11): 3019–3035. doi:10.1016/S0040-4020(01)96921-2. ISSN 0040-4020.
5. ↑ Casey, Martha L.; Kemp, D. S.; Paul, Kenneth G.; Cox, Daniel D. (June 1973). "Physical organic chemistry of benzisoxazoles. I. Mechanism of the base-catalyzed decomposition of benzisoxazoles". The Journal of Organic Chemistry 38 (13): 2294–2301. doi:10.1021/jo00953a006.
6. ↑ Kemp, D. S.; Cox, Daniel D.; Paul, Kenneth G. (December 1975). "Physical organic chemistry of benzisoxazoles. IV. Origins and catalytic nature of the solvent rate acceleration for the decarboxylation of 3-carboxybenzisoxazoles". Journal of the American Chemical Society 97 (25): 7312–7318. doi:10.1021/ja00858a018.
7. ↑ Kemp, Daniel S. (April 1970). "Decarboxylation of benzisoxazole-3-carboxylic acids. Catalysis by extraction of possible relevance to the problem of enzymic mechanism". Journal of the American Chemical Society 92 (8): 2553–2554. doi:10.1021/ja00711a061.

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*[CID]: Compound ID
*[H315]: Causes skin irritation
*[H319]: Causes serious eye irritation
*[H335]: May cause respiratory irritation
*[P261]: Avoid breathing dust/fume/gas/mist/vapours/spray
*[P264]: Wash … thoroughly after handling
*[P271]: Use only outdoors or in a well-ventilated area
*[P280]: Wear protective gloves/protective clothing/eye protection/face protection
*[P302+352]: IF ON SKIN: Wash with soap and water
*[P304+340]: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
*[P305+351+338]: IF IN EYES: Rinse continuously with water for several minutes. Remove contact lenses if present and easy to do – continue rinsing
*[P312]: Call a POISON CENTER or doctor/physician if you feel unwell
*[P321]: Specific treatment (see … on this label)
*[P332+313]: If skin irritation occurs: Get medical advice/attention
*[P337+313]: Get medical advice/attention
*[P362]: Take off contaminated clothing and wash before reuse
*[P403+233]: Store in a well ventilated place. Keep container tightly closed
*[P405]: Store locked up
*[P501]: Dispose of contents/container to …