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| | 2,1,3-Benzothiadiazole Basic information |
| Product Name: | 2,1,3-Benzothiadiazole | | Synonyms: | 3,4-Benzo-1,2,5-thiadiazole;Benzisothiadiazole;PIAZTHIOLE;2,1,3-BENZOTHIADIAZOLE;3,4-Benzo-1,2,5-thiodiazol;2.1.3-BENZOTHIADIAZOLE 99%;2,1,3-Benzothiadiazole,Piazthiole;Benzo-2,1,3-thiadiozole | | CAS: | 273-13-2 | | MF: | C6H4N2S | | MW: | 136.17 | | EINECS: | 205-985-2 | | Product Categories: | Medical Intermediates | | Mol File: | 273-13-2.mol |  |
| | 2,1,3-Benzothiadiazole Chemical Properties |
| Melting point | 42-44 °C (lit.) | | Boiling point | 206 °C (lit.) | | density | 1.323 (estimate) | | refractive index | 1.5300 (estimate) | | Fp | 203 °F | | storage temp. | Sealed in dry,Room Temperature | | solubility | Solubility in methanol almost transparent. | | form | Low Melting Solid | | pka | 0.37±0.33(Predicted) | | color | Colorless to white to pale yellow | | BRN | 112408 | | InChI | InChI=1S/C6H4N2S/c1-2-4-6-5(3-1)7-9-8-6/h1-4H | | InChIKey | PDQRQJVPEFGVRK-UHFFFAOYSA-N | | SMILES | N1=C2C=CC=CC2=NS1 | | CAS DataBase Reference | 273-13-2(CAS DataBase Reference) | | NIST Chemistry Reference | 2,1,3-Benzothiadiazole(273-13-2) | | EPA Substance Registry System | 2,1,3-Benzothiadiazole (273-13-2) |
| Risk Statements | 36/37/38 | | Safety Statements | 22-24/25-36/37/39-26 | | WGK Germany | 3 | | RTECS | DM2580000 | | TSCA | TSCA listed | | HS Code | 29349990 | | Storage Class | 11 - Combustible Solids |
| | 2,1,3-Benzothiadiazole Usage And Synthesis |
| Chemical Properties | Colorless to light brown solid | | Uses | The product is used as an industrial solvent, and pharmaceutical intermediates for organic synthesis and used nitrocellulose and other resin, wax, fatty, dyes and other solvents. | | Uses | 2,1,3-Benzothiadiazole is a chemical reagent used in the synthesis of supramolecules as well as the synthesis of benzothiadiazole derivatives via cross coupling. | | Reactions |
2,1,3-benzothiadiazole undergoes the standard chemistry of aromatic compounds, for example readily forming nitro and chloro derivatives.Under reducing conditions, it can be converted back to the 1,2-diaminobenzene compounds from which they were prepared.
| | Synthesis Reference(s) | The Journal of Organic Chemistry, 27, p. 676, 1962 DOI: 10.1021/jo01049a536 | | Synthesis | General procedure for the synthesis of 2,1,3-benzothiadiazole from o-phenylenediamine: 1,2-diaminobenzene (3.250 g, 30.05 mmol) and triethylamine (18 mL, 130.0 mmol) were dissolved in dichloromethane (20 mL). A solution of sulfuryl chloride (7.0 mL, 96.00 mmol) in dichloromethane (10 mL) was added dropwise with stirring. After completion of the reaction, the solvent was removed by rotary evaporator and the combined organic layers were concentrated under vacuum to afford the target product 2,1,3-benzothiadiazole (3.956 g, 97% yield). The melting point of the product was 43 °C. 1H NMR (CDCl3, 400 MHz, TMS) δ: 8.04-8.00 (m, 2H), 7.62-7.57 (m, 2H). | | References | [1] Dyes and Pigments, 2016, vol. 124, p. 268 - 276
[2] Chemistry of Heterocyclic Compounds (New York, NY, United States), 1989, vol. 25, # 11, p. 1303 - 1307
[3] Khimiya Geterotsiklicheskikh Soedinenii, 1989, # 11, p. 1555 - 1558
[4] Tetrahedron, 2005, vol. 61, # 46, p. 10975 - 10982
[5] Tetrahedron Letters, 2005, vol. 46, # 40, p. 6843 - 6846 |
| | 2,1,3-Benzothiadiazole Preparation Products And Raw materials |
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