| Revision as of 16:03, 16 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 475472859 of page 1,2,3-Triazole for the Chem/Drugbox validation project (updated: 'CASNo'). |
Latest revision as of 15:30, 14 May 2024 edit Chem Sim 2001 (talk | contribs)Extended confirmed users576 edits new structure in SVG format |
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}} |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443241645 |
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| ImageFileL1 = 1%2C2%2C3-triazole_numbering.png |
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| verifiedrevid = 477202367 |
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| ImageFileL1 = 1H-1,2,3-Triazole-2D-numbering.svg |
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| ImageFileR1 = 1%2C2%2C3-Triazole3d.png |
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| ImageSizeR1 = 100px |
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| ImageFileR1 = 1%2C2%2C3-Triazole3d.png |
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| IUPACName = 1''H''-1,2,3-triazole |
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| ImageSizeR1 = 100px |
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| OtherNames = 1,2,3-triazole |
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| PIN = 1''H''-1,2,3-Triazole |
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| Section1 = {{Chembox Identifiers |
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| OtherNames = 1,2,3-Triazole |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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|Section1={{Chembox Identifiers |
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| CASNo_Ref = {{cascite|changed|??}} |
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| CASNo = 288-36-8 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = EM7554254W |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI_Ref = {{ebicite|correct|EBI}} |
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| ChEBI = 35566 |
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| ChEBI = 35566 |
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| ChemSpiderID = 60839 |
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| ChemSpiderID = 60839 |
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| EINECS = 608-262-3 |
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| PubChem = 67516 |
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| InChI = 1/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) |
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| InChI = 1/C2H3N3/c1-2-4-5-3-1/h1-2H,(H,3,4,5) |
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| SMILES1 = c1cnn1 |
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| SMILES1 = c1cnn1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = QWENRTYMTSOGBR-UHFFFAOYSA-N |
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| StdInChIKey = QWENRTYMTSOGBR-UHFFFAOYSA-N |
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| SMILES = C1=CN=NN1 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| CASNo = <!-- blanked - oldvalue: 288-36-8 --> |
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| PubChem = |
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| SMILES = C1=CN=NN1 |
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| Section2 = {{Chembox Properties |
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| Formula = C<sub>2</sub>H<sub>3</sub>N<sub>3</sub> |
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| MolarMass = 69.0654 |
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| Appearance = colorless liquid |
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| Density = 1.192 |
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| MeltingPt = 23-25 °C |
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| BoilingPtC = 203 |
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| Solubility = very soluble |
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| pKa = 1.2 |
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| pKb = 9.4 |
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| Section7 = {{Chembox Hazards |
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| OtherCpds = ] ] |
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|Section2={{Chembox Properties |
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| Formula = C{{sub|2}}H{{sub|3}}N{{sub|3}} |
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| MolarMass = 69.0654 |
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| Appearance = colorless liquid |
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| Density = 1.192 |
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| MeltingPtC = 23 to 25 |
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| MeltingPt_notes = |
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| BoilingPtC = 203 |
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| Solubility = very soluble |
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| pKa = 9.4<ref name="1,2,3-triazole - an overview...">{{cite journal |date=1984 |title=1,2,3-triazole - an overview |url=https://www.sciencedirect.com/topics/chemistry/1-2-3-triazole |journal=Comprehensive Heterocyclic Chemistry}}</ref> |
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| pKb = 1.2<ref name="1,2,3-triazole - an overview..." /> |
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|Section7={{Chembox Hazards |
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| GHSPictograms = {{GHS07}} |
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| GHSSignalWord = Warning |
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| HPhrases = {{H-phrases|315|319|335}} |
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| PPhrases = {{P-phrases|261|264|271|280|302+352|304+340|305+351+338|312|321|332+313|337+313|362|403+233|405|501}} |
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| MainHazards = |
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| OtherCompounds = ] ] |
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'''1,2,3-Triazole''' is one of a pair of ]ic ]s with ] C{{sub|2}}H{{sub|3}}N{{sub|3}}, called ]s, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,3-Triazole is a basic ] ].<ref>{{cite book | title=Heterocyclic chemistry | first1= T.L. | last1=Gilchrist | publisher=Prentice Hall Press | year=1987 |isbn=0-582-01421-2}}</ref> |
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==Synthesis== |
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The unsubstituted ring can be produced by an oxidative coupling of ], ] and ].<ref>{{cite journal |last1=Song |first1=Lei |last2=Ang |first2=Hwee Ting |last3=Senthilperumal |first3=Jagadeesan |last4=Kanusu |first4=Umamaheswara Rao |last5=Venugopal |first5=Sivasankaran |last6=Rangarajan |first6=Naveen |last7=Krishnamoorthy |first7=Shivasankar |last8=Dubbaka |first8=Srinivas Reddy |last9=O’Neill |first9=Patrick |last10=Wu |first10=Jie |title=1,2,3-Triazole Synthesis: Development of Safe and Effective Batch and Continuous Manufacturing Processes |journal=Organic Process Research & Development |date=12 March 2024 |doi=10.1021/acs.oprd.4c00020}}</ref> |
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A wide range of methods exist for forming substituted 1,2,3-triazoles.<ref>{{cite journal |last1=Krivopalov |first1=Victor P |last2=Shkurko |first2=Oleg P |title=1,2,3-Triazole and its derivatives. Development of methods for the formation of the triazole ring |journal=Russian Chemical Reviews |date=30 April 2005 |volume=74 |issue=4 |pages=339–379 |doi=10.1070/RC2005v074n04ABEH000893}}</ref> These include the ] or the ] in which an ] and an ] undergo a ] reaction. Under thermal conditions, regioselectivity is substrate dependent. Selectivity can be increased with metal catalysts, which have the added benefit of reacting without excessive or extensive heating. Copper catalyzed cycloadditions favor 1,4-disubstituted triazoles, Ruthenium catalyzed cycloaddition favor 1,5-disubstituted triazoles. This chemistry was expanded by Zhu et al. in 2018 wherein they report a two-step sequence from a terminal alkyne to 4-cyano 1,5-disubstituted triazoles. <ref name=Zhu-2018>{{cite journal |last1=Liu |first1=P. |last2=Clark |first2=R. |last3=Zhu |first3=L. |title=Synthesis of 1‑Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4‑Cyano-1,2,3-triazoles|journal=] |year=2018 |volume=83|issue=9|pages=5092–5103 |doi=10.1021/acs.joc.8b00424|pmid=29630830 }}</ref> |
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==Properties== |
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The 2H-1,2,3-triazole tautomer is the major form in aqueous solution.<ref>{{cite journal | first1= Adrien | last1=Albert | first2= Peter J. | last2=Taylor | title=The tautomerism of 1,2,3-triazole in aqueous solution | journal=] | issue=11 | pages=1903–1905 | year=1989 | doi=10.1039/P29890001903}}</ref> |
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It is a surprisingly stable structure compared to other organic compounds with three adjacent nitrogen atoms. However, flash vacuum ] at 500 °C leads to loss of molecular nitrogen (N{{sub|2}}) leaving a three-member ] ring. Certain triazoles are relatively easy to cleave due to ]. One manifestation is found in the ]. |
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==Applications== |
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1,2,3-Triazole finds use in research as a ] in medicinal chemistry<ref>{{cite journal|author1=Bonandi, E. |author2=Christodoulou, M. S. |author3=Fumagalli, G. |author4=Perdicchia, D. |author5=Rastelli, G. |author6=Passarella, D.|title=The 1,2,3-triazole ring as a bioisostere in medicinal chemistry|journal=]|year=2017|volume=22|issue=10|pages=1572–1581 |pmid=28676407 |doi=10.1016/j.drudis.2017.05.014|hdl=11380/1153568|hdl-access=free}}</ref> building block for more complex chemical compounds, including pharmaceutical drugs such as ] and ]. |
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==References== |
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<references/> |
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{{DEFAULTSORT:Triazole, 1, 2, 3-}} |
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] |