Benzoxazole: Difference between revisions
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Benzoxazole3d.png |
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| ImageAlt = Skeletal formula with numbering convention |
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| ImageName1 = Benzoxazole |
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| ImageFile1 = Benzoxazole 2D aromatic full.svg |
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| IUPACName = benzoxazole<!-- e.g. Iron(II) chloride --> |
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| OtherNames = 1-Oxa-3-aza-1H-indene<!-- e.g. Ferrous chloride etc, + linked mineral names --> |
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| ImageAlt1 = Full structural formula with aromatic bond |
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| ImageFileL2 = Benzoxazole 3D ball inverted.png |
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| ImageSizeL2 = 140 |
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| ImageAltL2 = Ball-and-stick molecular model |
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| ImageFileR2 = Benzoxazole 3D spacefill inverted.png |
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| ImageSizeR2 = 130 |
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| ImageAltR2 = Space-filling molecular model |
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| OtherNames = 1-Oxa-3-aza-1''H''-indene |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| SMILES = n1c2ccccc2oc1 |
| SMILES = n1c2ccccc2oc1 |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 8873 |
| ChemSpiderID = 8873 |
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| InChI = 1/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H |
| InChI = 1/C7H5NO/c1-2-4-7-6(3-1)8-5-9-7/h1-5H |
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| CASNo_Ref = {{cascite|correct|CAS}} |
| CASNo_Ref = {{cascite|correct|CAS}} |
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| CASNo = 273-53-0 |
| CASNo = 273-53-0 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = J233Y1I55I |
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| PubChem = 9228 |
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|Section2={{Chembox Properties |
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|C=7|H=5|N=1|O=1 |
|C=7|H=5|N=1|O=1 |
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| Appearance = White to light yellow solid |
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| Density = |
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| Solubility = Insoluble |
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| MeltingPtC = 27 to 30 |
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| BoilingPtC = 182 |
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|Section7={{Chembox Hazards |
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| ExternalSDS = |
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| MainHazards = |
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| FlashPtC = 58 |
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| RPhrases = |
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|Section8={{Chembox Related |
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| OtherCompounds = [[oxazole]]<br />[[indole]]<br />[[benzofuran]] |
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'''Benzoxazole''' is an [[aromatic]] [[organic compound]] with a molecular formula C<sub>7</sub>H<sub>5</sub>NO, a [[benzene]]-fused [[oxazole]] ring structure, and an odor similar to [[pyridine]]. |
'''Benzoxazole''' is an [[aromatic]] [[organic compound]] with a molecular formula C<sub>7</sub>H<sub>5</sub>NO, 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. |
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Being a [[heterocyclic]] compound, benzoxazole finds use in research as a starting material for the synthesis of larger, usually bioactive structures. |
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. |
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==Occurrence and applications== |
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Its [[aromaticity]] makes it relatively stable, although as a heterocycle, it has reactive sites which allow for functionalization. |
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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 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> |
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<gallery> |
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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 |
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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> |
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</gallery> |
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==See also== |
==See also== |
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;Structural isomers |
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*[[Anthranil]], an analog with the [[oxygen]] [[atom]] in position 2 |
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*[[Benzisoxazole]], an analog with the [[nitrogen]] [[atom]] in position 2 |
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;Analogs |
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* [[Benzofuran]], an analog without the nitrogen atom. |
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* [[Benzimidazole]], an analog with the [[oxygen]] replaced by a nitrogen |
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* [[Benzoxazoline]], which has one double bond reduced. |
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* [[Benzothiazole]], an analog with the oxygen replaced by a sulfur |
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* [[Benzoxazolidinedione]], which has both double bonds reduced. |
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* [[Benzoxazolidine]], which has both double bonds reduced. |
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* [[Benzoxazolidinone]] |
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==References== |
==References== |
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{{reflist|2}} |
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{{Unreferenced|date =September 2007}} |
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<references/> |
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[[Category:Aromatic bases]] |
[[Category:Aromatic bases]] |
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[[Category:Benzoxazoles| ]] |
[[Category:Benzoxazoles| ]] |
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[[Category:Simple aromatic rings]] |
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[[Category:Foul-smelling chemicals]] |
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[[nl:Benzoxazool]] |
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[[ja:ベンゾオキサゾール]] |
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[[ru:Бензоксазол]] |