Benzoxazole: Difference between revisions

| 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-1''H''-indene

|Section1={{Chembox Identifiers

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

| ChEBI = 38814

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

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

| UNII = J233Y1I55I

| PubChem = 9228

| RTECS =

|Section2={{Chembox Properties

| 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]]<br />[[indole]]<br />[[benzofuran]]

'''Benzoxazole''' is an [[aromatic]] [[organic compound]] with a molecular formula C₇H₅NO, a [[benzene]]-fused [[oxazole]] ring structure, and an odor similar to [[pyridine]].<ref name="Katritzky2nd">{{Katritzky2nd}}</ref><ref name="Clayden1st">{{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 }}</ref> 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 brightener]]s in laundry detergents.<ref name=Ullmann>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}}</ref> Benzoxazoles belong to the group of well-known antifungal agents with antioxidant, antiallergic, antitumoral and antiparasitic activity.<ref>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.</ref>

<gallery>

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

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 brightener]]s, e.g. in laundry detergents<ref>{{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 }}</ref>

</gallery>

;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

* [[Indole|Benzopyrrole or indole]], an analog without the oxygen atom

* [[Benzofuran]], an analog without the nitrogen atom

{{reflist|2}}

{{Simple aromatic rings}}

[[Category:Simple aromatic rings]]

[[Category:Foul-smelling chemicals]]