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Benzoxazole

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Benzoxazole
Skeletal formula with numbering convention
Full structural formula with aromatic bond
Ball-and-stick molecular model
Space-filling molecular model
Names
Preferred IUPAC name
1,3-Benzoxazole
Other names
1-Oxa-3-aza-1H-indene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.005.445 Edit this at Wikidata
UNII
  • InChI=1S/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H checkY
    Key: BCMCBBGGLRIHSE-UHFFFAOYSA-N checkY
  • InChI=1/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H
    Key: BCMCBBGGLRIHSE-UHFFFAOYAP
  • n1c2ccccc2oc1
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
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 checkY☒N ?)

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

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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]

See also

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Structural isomers
Analogs

References

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  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. ^ 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. PMID 21916450.