Benzisoxazole

Chemical compound From Wikipedia, the free encyclopedia

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
Skeletal formula with numbering convention
Ball-and-stick molecular model
Space-filling molecular model
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 Edit this at Wikidata
EC Number
  • 205-983-1
UNII
  • InChI=1S/C7H5NO/c1-2-4-7-6(3-1)5-8-9-7/h1-5H checkY
    Key: KTZQTRPPVKQPFO-UHFFFAOYSA-N checkY
  • 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 Â°C (95 to 100 Â°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 Â°C (136 Â°F; 331 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 Â°C [77 Â°F], 100 kPa).
☒N verify (what is checkY☒N ?)
Close

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]

Synthesis of 1,2-Benzisoxazol aus Salicylaldehyd und HOSA
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

References

Related Articles

Wikiwand AI