Benzoxazole

Benzoxazole
Skeletal formula with numbering convention
Full structural formula with aromatic bond
Ball-and-stick molecular model
Space-filling molecular model
Names
IUPAC name
benzoxazole
Other names
1-Oxa-3-aza-1H-indene
Identifiers
273-53-0 YesY
ChEBI CHEBI:38814 YesY
ChEMBL ChEMBL451894 YesY
ChemSpider 8873 YesY
Jmol interactive 3D Image
PubChem 9228
Properties
C7H5NO
Molar mass 119.12 g·mol−1
Appearance white to light yellow solid
Melting point 27 to 30 °C (81 to 86 °F; 300 to 303 K)
Boiling point 182 °C (360 °F; 455 K)
insol.
Hazards
Flash point 58 °C (136 °F; 331 K)
Related compounds
Related compounds
oxazole
indole
benzofuran
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Benzoxazole is an aromatic organic compound with a molecular formula C7H5NO, a benzene-fused oxazole ring structure, and an odor similar to pyridine.[1][2] Alhtough benzoxazole itself is of little practical value, many derivatives of benzoxazoles are commercially important.

Being a heterocyclic compound, benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. Its aromaticity makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization.

Occurrence and Applications

It is found within the chemical structures of pharmaceutical drugs such as flunoxaprofen. Benzoxazole derivatives are also of interest for optical brighteners in laundry detergents.[3] Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity.[4]

4 4'-bis(benzoxazolyl)-cis-stilbene is an intensely fluorescent and its derivatives are used as optical brighteners.
2 5-bis(benzoxazol-2-yl)thiophene is also an intensely fluorescent and its derivatives are used as optical brighteners, e.g. in laundry detergents.[5]

See also

References

  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. E. Smulders, E. Sung "Laundry Detergents, 2. Ingredients and Products" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012. doi:10.1002/14356007.o15_013
  4. Şener, E., Yalçin, İ. and Sungur, E.: QSAR of some antifungal benzoxazoles and oxazolo(4,5-b)pyridines against C. Albicans. Quant. Struct.-Act. Relat. 10 (1991) 223-228.
  5. M. Amine Fourati, Thierry Maris, W. G. Skene, C. Géraldine Bazuin, and Robert E. Prud’homme "Photophysical, Electrochemical and Crystallographic Investigations of the Fluorophore 2,5-Bis(5-tert-butyl-benzoxazol-2-yl)thiophene" J. Phys. Chem. B, 2011, volume 115, 12362–12369.doi:10.1021/jp207136k
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