1,2,4-Triazole

changed 477202680 Structural formula of 1,2,4-Triazole.svg 1%2C2%2C4-Triazole3d.png 1H-1,2,4-Triazole 1,2,4-Triazole pyrrodiazole correct chemspider correct EBI 46077 8900 1/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5) NSPMIYGKQJPBQR-UHFFFAOYAZ correct EBI 15571 correct chemspider 1S/C2H3N3/c1-3-2-5-4-1/h1-2H,(H,3,4,5) correct chemspider NSPMIYGKQJPBQR-UHFFFAOYSA-N correct CAS 288-88-0 correct FDA 10MS0Y1RDI 9257 N1C=NC=N1 C2H3N3 69.00725 white solid 1.439 g/cm3 120 to 121 260 very soluble 10,3 11,8 140 1,2,3-triazole imidazole 1,2,4-Triazole (as ligand in coordination compounds, Htrz abbreviation is sometimes used) is one of a pair of isomeric chemical compounds with molecular formula C2H3N3, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,4-Triazole and its derivatives find use in a wide variety of applications. The Chemistry of 1,2,4-Triazoles. Potts K. T. Chemical Reviews 61 2 87–127 1961 10.1021/cr60210a001 1961ChRv...61...87P Structure and properties 1,2,4-Triazole is a planar molecule. The C-N and N-N distances fall into a narrow range 136 - 132 picometers, consistent with the aromaticity.10.1107/S010876818300258X Neutron diffraction at 15 and 120 K and ab initio molecular-orbital studies of the molecular structure of 1,2,4-triazole 1983 Jeffrey G. A. Ruble J. R. Yates J. H. Acta Crystallographica Section B: Structural Science 39 3 388–394 1983AcCrB..39..388J Although two tautomers can be envisioned, only one exists practically speaking. 1,2,4-Triazole is amphoteric, being susceptible to both N-protonation and deprotonation in aqueous solution. The pKa of 1,2,4-triazolium (C2N3H4+) is 2.45. The pKa of the neutral molecule is 10.26.10.1016/B978-008096518-5.00080-0 1,2,4-Triazoles Comprehensive Heterocyclic Chemistry II 1996 Garratt Peter J. 127–163 978-0-08-096518-5 Synthesis and occurrence thumb|left|Portion of the structure of {[Fe(triazolate)(triazole)2](BF4)}n.10.1002/ejic.201201121 Crystal Structures and Spin Crossover in the Polymeric Material [Fe(HTRZ)2(TRZ)](BF4) Including Coherent-Domain Size Reduction Effects 2013 Grosjean Arnaud Négrier Philippe Bordet Pierre Etrillard Céline Mondieig Denise Pechev Stanislav Lebraud Eric Létard Jean-François Guionneau Philippe European Journal of Inorganic Chemistry 2013 5–6 796–802 https://hal.archives-ouvertes.fr/hal-00794417/file/GrosjeanEJIC2013_Postprint.pdf 1,2,4-Triazoles can be prepared using the Einhorn–Brunner reaction or the Pellizzari reaction. In 2018, it was reported that reaction of isonitriles with diazonium salts produced 2,3-disubstituted or 2,5-disubstituted 1,2,4-triazoles depending on the catalyst.Liu Jian-Quan Shen Xuanyu Wang Yihan Wang Xiang-Shan Bi Xihe [3 + 2] Cycloaddition of Isocyanides with Aryl Diazonium Salts: Catalyst-Dependent Regioselective Synthesis of 1,3- and 1,5-Disubstituted 1,2,4-Triazoles Organic Letters 2018 20 21 6930–6933 10.1021/acs.orglett.8b03069 30339399 https://pubs.acs.org/doi/10.1021/acs.orglett.8b03069#:~:text=Isocyanides%20are%20extraordinarily%20versatile%20building,(Figure%201a) subscription Unsubstituted 1,2,4-triazole can be prepared from thiosemicarbazide by acylation with formic acid followed by cyclization of 1-formyl-3-thiosemicarbazide into 1,2,4-triazole-3(5)-thiol; oxidation of the thiol by nitric acid or hydrogen peroxide yields 1,2,4-triazole.10.15227/orgsyn.040.0099 free C. Ainsworth 1,2,4-Triazole Organic Syntheses 1960 40 99 1,2,4-Triazoles are featured in many kinds of drugs.10.1111/cbdd.12527 Triazole: A Promising Antitubercular Agent 2015 Keri Rangappa S. Patil Siddappa A. Budagumpi Srinivasa Nagaraja Bhari Mallanna Chemical Biology & Drug Design 86 4 410–423 25643871 9313180 10.2174/1871520615666150819121106 Recent Developments on 1,2,4-Triazole Nucleus in Anticancer Compounds: A Review 2016 Kaur Ramandeep Ranjan Dwivedi Ashish Kumar Bhupinder Kumar Vinod Anti-Cancer Agents in Medicinal Chemistry 16 4 465–489 26286663 Notable triazoles include the antifungal drugs fluconazole and itraconazole10.1016/j.bmc.2012.04.045 The biology and chemistry of antifungal agents: A review 2012 Kathiravan Muthu K. Salake Amol B. Chothe Aparna S. Dudhe Prashik B. Watode Rahul P. Mukta Maheshwar S. Gadhwe Sandeep Bioorganic & Medicinal Chemistry 20 19 5678–5698 22902032 and the plant growth regulator paclobutrazol.A review on: Response of crops to paclobutrazol application Wakjira Tesfahun Fatih Yildiz January 1, 2018 Cogent Food & Agriculture 4 1 1–9 10.1080/23311932.2018.1525169 134517280 free 2018CogFA...425169T Triazolate is a common bridging ligand in coordination chemistry.10.1016/S0010-8545(00)00266-6 Mononuclear, oligonuclear and polynuclear metal coordination compounds with 1,2,4-triazole derivatives as ligands 2000 Haasnoot Jaap G. Coordination Chemistry Reviews 200-202 131–185 The 3,5dihydroxy derivative, known as urazole, sees extensive industrial use as a blowing agent.Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy 59 3 Feb 2003 637–650 Vibrational frequencies and structural determinations of urazole James O. Jensen 10.1016/S1386-1425(02)00210-X 12524134 2003AcSpA..59..637J References Category:Triazoles Category:Organic compounds with 2 carbon atoms