benzoxazole

{{chembox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = 443417538

| Name = Benzoxazole

| ImageFile_Ref = {{chemboximage|correct|??}}

| ImageFile = 1,3-benzoxazole numbering.svg

| ImageSize = 160

| ImageAlt = Skeletal formula with numbering convention

| ImageFile1 = Benzoxazole 2D aromatic full.svg

| ImageSize1 = 160

| ImageAlt1 = Full structural formula with aromatic bond

| ImageFileL2 = Benzoxazole 3D ball inverted.png

| ImageSizeL2 = 140

| ImageAltL2 = Ball-and-stick molecular model

| ImageFileR2 = Benzoxazole 3D spacefill inverted.png

| ImageSizeR2 = 130

| ImageAltR2 = Space-filling molecular model

| PIN = 1,3-Benzoxazole

| OtherNames = 1-Oxa-3-aza-1H-indene

|Section1={{Chembox Identifiers

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 38814

| SMILES = n1c2ccccc2oc1

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 8873

| InChI = 1/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H

| InChIKey = BCMCBBGGLRIHSE-UHFFFAOYAP

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 451894

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BCMCBBGGLRIHSE-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo = 273-53-0

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = J233Y1I55I

| PubChem = 9228

| RTECS =

}}

|Section2={{Chembox Properties

|C=7|H=5|N=1|O=1

| Appearance = White to light yellow solid

| Density =

| Solubility = Insoluble

| MeltingPtC = 27 to 30

| BoilingPtC = 182

}}

|Section7={{Chembox Hazards

| ExternalSDS =

| MainHazards =

| FlashPtC = 58

}}

|Section8={{Chembox Related

| OtherCompounds = oxazole
indole
benzofuran

}}

}}

Benzoxazole is an aromatic organic compound with a molecular formula C7H5NO, a benzene-fused oxazole ring structure, and an odor similar to pyridine.{{Katritzky2nd}}{{cite book |last1=Clayden |first1=J. |last2=Greeves |first2=N. |last3=Warren |first3=S. |last4=Wothers |first4=P. |title=Organic Chemistry |publisher=Oxford University Press |location=Oxford, Oxfordshire |year=2001 |isbn=0-19-850346-6 |url=https://archive.org/details/organicchemistry00clay_0 |url-access=registration }} 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.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}} Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity.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.

4 4-bis(benzoxazolyl)-cis-stilbene.svg|4,4'-(E)-bis(benzoxazolyl)stilbene is intensely fluorescent and its derivatives are used as optical brighteners

2 5-bis(benzoxazol-2-yl)thiophene.svg|2,5-bis(benzoxazol-2-yl)thiophene is also intensely fluorescent and its derivatives are used as optical brighteners, e.g. in laundry detergents{{cite journal|last1=Fourati|first1=M. Amine|last2=Maris|first2=Thierry|last3=Skene|first3=W. G.|last4=Bazuin|first4=C. Géraldine|last5=Prud’homme|first5=Robert E.|title=Photophysical, Electrochemical and Crystallographic Investigations of the Fluorophore 2,5-Bis(5-tert-butyl-benzoxazol-2-yl)thiophene|journal=The Journal of Physical Chemistry B|date=3 November 2011|volume=115|issue=43|pages=12362–12369|doi=10.1021/jp207136k|pmid=21916450 }}

See also

;Structural isomers

;Analogs

References