Benzoxazole Explained

Benzoxazole is an aromatic organic compound with a molecular formula C₇H₅NO, a benzene-fused oxazole ring structure, and an odor similar to pyridine.^[1] Although 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 and tafamidis. Benzoxazole derivatives are also of interest for optical brighteners in laundry detergents.^[2] Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity.^[3]

See also

Structural isomers

• Anthranil, an analog with the oxygen atom in position 2
• Benzisoxazole, an analog with the nitrogen atom in position 2

Analogs

• Benzimidazole, an analog with the oxygen replaced by a nitrogen
• Benzothiazole, an analog with the oxygen replaced by a sulfur
• Benzopyrrole or indole, an analog without the oxygen atom
• Benzofuran, an analog without the nitrogen atom

Notes and References

1. Book: Clayden . J. . Greeves . N. . Warren . S. . Wothers . P. . Organic Chemistry . Oxford University Press . Oxford, Oxfordshire . 2001 . 0-19-850346-6 . registration .
2. E. Smulders, E. Sung "Laundry Detergents, 2. Ingredients and Products" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2012.
3. 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.