Benzisoxazole

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Not to be confused with 2,1-Benzisoxazole.
Benzisoxazole
Skeletal formula with numbering convention
Ball-and-stick molecular model
Space-filling molecular model
Names
Preferred IUPAC name
1,2-Benzisoxazole
Other names
Benzo[d]isoxazole; Indoxazine
Identifiers
3D model (Jmol)
ChEBI
ChemSpider
Properties
C7H5NO
Molar mass 119.12 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
S-phrases S24/25, S28A, S37, S45
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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Infobox references

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.

Synthesis[edit]

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

See also[edit]

Structural isomers

References[edit]

  1. ^ Katritzky, A. R.; Pozharskii, A. F. (2000). Handbook of Heterocyclic Chemistry (2nd ed.). Academic Press. ISBN 0080429882. 
  2. ^ Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6. 
  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.