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| | 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one Basic information |
| Product Name: | 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one | | Synonyms: | 1,2,4-TRIAZOLE(4,3)PYRIDIN-3-(2H)-ONE;1,2,4-TRIAZOL-(4,3-A)-PYRIDINE 3 (2H)-ONE;1,2,4-Triazolopyridin-3-one;3-HYDROXYTRIAZOLO[4,3-A]PYRIDINE;3-HYDROXY-1,2,4-TRIAZOLO[4,3-A]PYRIDINE;1,2,4-Triazole-(4,3-alpha)pyri;Trazodone Impurity 15;2,4-Triazolopyridin-3-one | | CAS: | 6969-71-7 | | MF: | C6H5N3O | | MW: | 135.12 | | EINECS: | 230-191-8 | | Product Categories: | Heterocycles;intermediate for some organic synthesis;Fused Ring Systems;Pyridines;APIs & Intermediate;Pyrimidine | | Mol File: | 6969-71-7.mol | ![1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one Structure](CAS/GIF/6969-71-7.gif) |
| | 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one Chemical Properties |
| Melting point | 231°C | | density | 1.51±0.1 g/cm3(Predicted) | | storage temp. | 2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly, Heated, Sonicated) | | pka | 7.86±0.20(Predicted) | | form | Solid | | color | Light Brown to Brown | | BRN | 607433 | | Stability: | Light Sensitive | | InChI | InChI=1S/C6H5N3O/c10-6-8-7-5-3-1-2-4-9(5)6/h1-4H,(H,8,10) | | InChIKey | LJRXNXBFJXXRNQ-UHFFFAOYSA-N | | SMILES | C12=NNC(=O)N1C=CC=C2 | | LogP | 0.113 | | CAS DataBase Reference | 6969-71-7(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
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| | 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one Usage And Synthesis |
| Chemical Properties | Beige Solid | | Uses | 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one was used to prepare a congener of Trazodone (T718500) which was found to be a potent and selective inhibitor of synaptosomal uptake of 5-hydroxytryptamine. | | Synthesis Reference(s) | Journal of Medicinal Chemistry, 28, p. 1394, 1985 DOI: 10.1021/jm00148a004 | | Synthesis | General procedure for the synthesis of [1,2,4]triazolo[4,3-a]pyridin-3-(2H)-one from 2-chloropyridine and aminourea hydrochloride: 2-chloropyridine (5.0 g, 44.03 mmol), aminourea hydrochloride (9.8 g, 88.06 mmol), and 2-ethoxyethanol (15 mL) were mixed and heated to reflux. Concentrated hydrochloric acid (0.1 mL dissolved in 1 mL of 2-ethoxyethanol) was slowly added to the reaction mixture. The reaction was kept at reflux for 24 hours and subsequently cooled to about 60 °C and diluted with deionized water (15 mL). The resulting light yellow solid product was collected by filtration and washed with deionized water to afford the title compound (2.2 g, 51% yield). The melting point of the product was 235-240°C. 1H NMR (300 MHz, DMSO-d6) δ 6.51-6.60 (m, 1H), 7.05-7.22 (m, 2H), 7.80 (d, J=7.1 Hz, 1H), 12.45 (br, 1H, exchangeable with D2O); IR (KBr) ν 3173, 3098. 3048, 1717, 1634, 1536, 1348 cm-1; MS 136 (M+1). | | References | [1] Patent: US2009/209550, 2009, A1. Location in patent: Page/Page column 25-26
[2] Patent: US4254124, 1981, A |
| | 1,2,4-Triazolo[4,3-a]pyridin-3(2H)-one Preparation Products And Raw materials |
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