Benzisoxazole

Chemical compound From Wikipedia, the free encyclopedia

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.

Quick Facts Names, Identifiers ...
Benzisoxazole
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Names
Preferred IUPAC name
1,2-Benzoxazole
Other names
Benzo[d]isoxazole; Indoxazine
Identifiers
3D model (JSmol)
2154
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.440
EC Number
  • 205-983-1
UNII
  • 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
  • n2oc1ccccc1c2
Properties
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 labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, 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).
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Its aromaticity makes it relatively stable;[3] however, it is only weakly basic.

Synthesis

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

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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.

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See also

Structural isomers

References

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