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Saving copy of the {{chembox}} taken from revid 469519765 of page 1-Hydroxy-7-azabenzotriazole for the Chem/Drugbox validation project (updated: 'CASNo').
 
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{{redirect|HOAt}}
{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid [{{fullurl:1-Hydroxy-7-azabenzotriazole|oldid=469519765}} 469519765] of page [[1-Hydroxy-7-azabenzotriazole]] with values updated to verified values.}}
{{chembox
{{chembox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 457642967
| verifiedrevid = 477207891
|ImageFile=1-hydroxy-7-aza-benzotriazole.svg
| ImageFile=1-hydroxy-7-aza-benzotriazole.svg
|ImageSize=150px
| ImageSize=150px
| ImageAlt = Skeletal formula of HOAt
|IUPACName=
| ImageFile1 = 1-Hydroxy-7-azabenzotriazole molecule spacefill from xtal.png
|OtherNames=
| ImageSize1 = 150
| ImageAlt1 = Space-filling model of the HOAt molecule
| PIN = 3''H''-[1,2,3]Triazolo[4,5-''b'']pyridin-3-ol
|Section1={{Chembox Identifiers
|Section1={{Chembox Identifiers
| InChI = 1/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H
| InChI = 1/C5H4N4O/c10-9-5-4(7-8-9)2-1-3-6-5/h1-3,10H
| InChIKey = FPIRBHDGWMWJEP-UHFFFAOYAJ
| InChIKey = FPIRBHDGWMWJEP-UHFFFAOYAJ
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FPIRBHDGWMWJEP-UHFFFAOYSA-N
| StdInChIKey = FPIRBHDGWMWJEP-UHFFFAOYSA-N
| CASNo_Ref = {{cascite|changed|??}}
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = <!-- blanked - oldvalue: 39968-33-7 -->
| CASNo=39968-33-7
| UNII_Ref = {{fdacite|correct|FDA}}
| PubChem=181649
| UNII = TX8XYH09H0
| SMILES = n1cccc2nnn(O)c12
| PubChem=181649
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| SMILES = n1cccc2nnn(O)c12
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID=158005
| ChemSpiderID=158005
}}
}}
|Section2={{Chembox Properties
|Section2={{Chembox Properties
| C=5 | H=4 | N=4 | O=1
| C=5 | H=4 | N=4 | O=1
| Density= 0.973 g/mL
| Appearance=
| MeltingPt= 213-216°C
| Density=
}}
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
|Section3={{Chembox Hazards
| GHSPictograms = {{GHS01}} {{GHS05}} {{GHS06}} {{GHS07}}
| EUClass = {{Hazchem T}}
| GHSSignalWord = danger
| FlashPt=
| HPhrases = {{HPhrases|H204|H301|H302|H315|H318|H319|H335}}
| Autoignition=
| PPhrases = {{PPhrases|P210|P240| P250|P261| P264| P270| P271| P280| P301+P310| P301+P312|P302+P352|P304+P340| P305+P351+P338| P310| P312| P321| P330| P332+P313| P337+P313|P362|P370+P380|P372| P373| P374| P401 |P403+P233 |P405|P501}}
}}
| GHS_ref = <ref>GHS: [https://www.sigmaaldrich.com/product/ALDRICH/445452 Sigma Aldrich 445452]</ref>
}}
}}
}}

'''1-Hydroxy-7-azabenzotriazole''' ('''HOAt''') is a [[triazole]] used as a [[peptide coupling reagent]].<ref>{{Cite journal | doi = 10.1021/ja00063a082| title = 1-Hydroxy-7-azabenzotriazole. An efficient peptide coupling additive| journal = Journal of the American Chemical Society| volume = 115| issue = 10| pages = 4397–4398| year = 1993| last1 = Carpino| first1 = Louis A}}</ref> It suppresses [[racemization]] that can otherwise occur during the reaction.<ref>{{cite journal|title=Amide bond formation: beyond the myth of coupling reagents|last1=Valeur|first1=Eric|last2=Bradley|first2=Mark|journal=Chemical Society Reviews|year=2009|volume=38|issue=2|pages=606–631|doi=10.1039/b701677h|pmid=19169468}}</ref>
HOAt has a melting point between 213 and 216 degrees Celsius.<ref>{{Cite web| url=https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3256884.htm| title=HOAt|website=Chemical Book|access-date=January 30, 2019}}</ref> As a liquid, it is transparent and without any color.

==References==
{{reflist}}

{{DEFAULTSORT:Hydroxy-7-azabenzotriazole, 1-}}
[[Category:Peptide coupling reagents]]
[[Category:Triazolopyridines]]
[[Category:Reagents for biochemistry]]
[[Category:Hydroxylamines]]

{{heterocyclic-stub}}