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| | 7-bromo-benzo[c][1,2,5]thiadiazole-4-carbaldehyde Basic information |
| Product Name: | 7-bromo-benzo[c][1,2,5]thiadiazole-4-carbaldehyde | | Synonyms: | 7-Bromo-4-formyl-2,1,3-benzothiadiazole;7-Bromo-2,1,3-benzothiadiazole-4-carboxaldehyde >=97%;2,1,3-Benzothiadiazole-4-carboxaldehyde, 7-bromo-;7-BROMOBENZO[1,25]THIOADIAZOLE-4-CARBALDEHYDE;7-bromo-benzo[c][1,2,5]thiadiazole-4-carbaldehyde;7-Bromo-2,1,3-benzothiadiazole-4-carbaldehyde;7-Bromo-2,1,3-benzothiadiazole-4-carboxaldehyde;7-Bromo-benzo[1,2,5]thiadiazole-4-carbaldehyde | | CAS: | 1071224-34-4 | | MF: | C7H3BrN2OS | | MW: | 243.08 | | EINECS: | | | Product Categories: | | | Mol File: | 1071224-34-4.mol | ![7-bromo-benzo[c][1,2,5]thiadiazole-4-carbaldehyde Structure](CAS/20180629/GIF/1071224-34-4.gif) |
| | 7-bromo-benzo[c][1,2,5]thiadiazole-4-carbaldehyde Chemical Properties |
| Melting point | 192.0 to 196.0 °C | | Boiling point | 355.0±27.0 °C(Predicted) | | density | 1.909±0.06 g/cm3(Predicted) | | storage temp. | 2-8°C | | pka | -2.54±0.50(Predicted) | | form | powder to crystal | | color | White to Yellow to Orange | | InChI | InChI=1S/C7H3BrN2OS/c8-5-2-1-4(3-11)6-7(5)10-12-9-6/h1-3H | | InChIKey | VPDPNJVAWKCZEH-UHFFFAOYSA-N | | SMILES | N1=C2C(Br)=CC=C(C=O)C2=NS1 |
| Hazard Codes | Xn | | Risk Statements | 22 | | WGK Germany | 3 | | HS Code | 2934.99.4400 |
| | 7-bromo-benzo[c][1,2,5]thiadiazole-4-carbaldehyde Usage And Synthesis |
| Synthesis | General procedure for the synthesis of 7-bromo-4-formylbenzo[C][1,2,5]thiadiazole from 4-bromo-7-(dibromomethyl)benzo[C][1,2,5]thiadiazole: aqueous silver nitrate (285 mg, 1.68 mmol, dissolved in 1.7 mL of water) was added to a stirred solution of compound A (260 mg, 0.67 mmol) in acetonitrile (8 mL) , followed by heating and refluxing for 2 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was filtered to remove the resulting AgBr precipitate. The filtrate was extracted with dichloromethane, the organic phases were combined, washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The solvent was removed by rotary evaporation to afford compound B (7-bromo-2,1,3-benzothiadiazole-4-carbaldehyde) as a white solid (147 mg, 92% yield). The physical and spectral data of compound B were as follows: melting point 185-186 °C; IR (KBr) ν 3078, 3021, 2835, 2728, 1702, 1526, 1268, 1102, 937, 879 cm?1; 1H NMR (CDCl3, 400 MHz) δ 10.71 (s, 1H), 8.09-8.03 (m, 2H); 13C NMR (CDCl3, 100 MHz) δ 188.0, 153.8, 152.1, 131.9, 131.5, 126.7, 121.7; HRMS (FAB+) m/z Calculated value C7H379BrN2OS [M]+ 241.9149, Measured value 241.9149; Calculated value C7H381BrN2OS [M]+ 243.9129, measured value 243.9137. | | References | [1] Journal of the American Chemical Society, 2015, vol. 137, # 2, p. 898 - 904
[2] Journal of the American Chemical Society, 2011, vol. 133, # 40, p. 15822 - 15825
[3] Patent: US8802975, 2014, B2. Location in patent: Page/Page column 7
[4] Tetrahedron Letters, 2010, vol. 51, # 33, p. 4462 - 4465 |
| | 7-bromo-benzo[c][1,2,5]thiadiazole-4-carbaldehyde Preparation Products And Raw materials |
| Raw materials | 4-BROMO-7-BROMOMETHYL-BENZO[1,2,5]THIADIAZOLE-->2,3-DIAMINOTOLUENE-->4-BroMo-7-(dibroMoMethyl)benzo[c][1,2,5]thiadiazole-->4-METHYL-2,1,3-BENZOTHIADIAZOLE-->4-BROMO-7-METHYL-BENZO[1,2,5]THIADIAZOLE-->Acetonitrile-->3-Methyl-2-nitroaniline-->Silver nitrate-->Water | | Preparation Products | 7-bromobenzo[c][1,2,5]thiadiazole-4-carbonitrile |
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