Benzoxazole
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Names | |||
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Preferred IUPAC name
1,3-Benzoxazole | |||
Other names
1-Oxa-3-aza-1H-indene
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Identifiers | |||
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3D model (JSmol)
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ChEBI | |||
ChEMBL | |||
ChemSpider | |||
ECHA InfoCard | 100.005.445 ![]() | ||
PubChem CID
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UNII | |||
CompTox Dashboard (EPA)
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Properties | |||
C7H5NO | |||
Molar mass | 119.123 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) | ||
Insoluble | |||
Hazards | |||
Flash point | 58 °C (136 °F; 331 K) | ||
Related compounds | |||
Related compounds
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oxazole indole benzofuran | ||
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 | |||
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] 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.[3] Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity.[4]
4,4'-(E)-bis(benzoxazolyl)stilbene is intensely fluorescent and its derivatives are used as optical brighteners
2,5-bis(benzoxazol-2-yl)thiophene is also intensely fluorescent and its derivatives are used as optical brighteners, e.g. in laundry detergents[5]
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
References[]
- ^ Katritzky, A. R.; Pozharskii, A. F. (2000). Handbook of Heterocyclic Chemistry (2nd ed.). Academic Press. ISBN 0080429882.
- ^ Clayden, J.; Greeves, N.; Warren, S.; Wothers, P. (2001). Organic Chemistry. Oxford, Oxfordshire: Oxford University Press. ISBN 0-19-850346-6.
- ^ 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
- ^ 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.
- ^ Fourati, M. Amine; Maris, Thierry; Skene, W. G.; Bazuin, C. Géraldine; Prud’homme, Robert E. (3 November 2011). "Photophysical, Electrochemical and Crystallographic Investigations of the Fluorophore 2,5-Bis(5-tert-butyl-benzoxazol-2-yl)thiophene". The Journal of Physical Chemistry B. 115 (43): 12362–12369. doi:10.1021/jp207136k.
- Aromatic bases
- Benzoxazoles
- Simple aromatic rings
- Foul-smelling chemicals