Introduction：Basic information about 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE CAS 452-35-7, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Basic information
| Product Name: | 6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE |
| Synonyms: | 6-ETHOXYZOLAMIDE;6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE;ETHOXZOLAMIDE;2-Benzothiazolesulfonamide, 6-ethoxy-;6-Ethoxy-1,3-benzothiazole-2-sulfonamide;L-643786;PNU-4191;6-ethoxy-2-benzothiazolesulfonamid |
| CAS: | 452-35-7 |
| MF: | C9H10N2O3S2 |
| MW: | 258.32 |
| EINECS: | 207-199-5 |
| Product Categories: | ANTIZOL |
| Mol File: | 452-35-7.mol |
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6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Chemical Properties
| Melting point | 190-193 °C(lit.) |
| Boiling point | 464.9±37.0 °C(Predicted) |
| density | 1.4767 (rough estimate) |
| refractive index | 1.6800 (estimate) |
| storage temp. | Refrigerator |
| solubility | DMSO (Slightly), Ethyl Acetate (Slightly) |
| pka | pKa 8.12(H2O t=25.0) (Uncertain) |
| form | Solid |
| color | Off-White |
| Water Solubility | 10.33mg/L(25 ºC) |
| Merck | 13,3790 |
| InChI | InChI=1S/C9H10N2O3S2/c1-2-14-6-3-4-7-8(5-6)15-9(11-7)16(10,12)13/h3-5H,2H2,1H3,(H2,10,12,13) |
| InChIKey | OUZWUKMCLIBBOG-UHFFFAOYSA-N |
| SMILES | S1C2=CC(OCC)=CC=C2N=C1S(N)(=O)=O |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36/37/38 |
| Safety Statements | 26 |
| WGK Germany | 3 |
| RTECS | DL6390000 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazardous Substances Data | 452-35-7(Hazardous Substances Data) |
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Usage And Synthesis
| Originator | Cardrase,Upjohn,US,1957 |
| Uses | alcohol dehydrogenase inhibitor, antidote |
| Uses | Ethoxzolamide is used in the treatment of glaucoma, and is also used as a diuretic, acting as a carbonic anhydrase inhibitor. |
| Definition | ChEBI: 1,3-Benzothiazole substituted a sulfonamide and an ethoxy group at positions 2 and 6, respectively. A carbonic anhydrase inhibitor, it has been used in the treatment of glaucoma, and as a diuretic. |
| Manufacturing Process | Preparation of 6-Ethoxybenzothiazole-2-Sulfenamide: A solution prepared bydissolving 21.0 grams (0.1 mol) of 6-ethoxybenzothiazole-2-thiol, Sebrell andBoord, J. Am. Chem. Soc. 45: 2390 to 2399 (1923), in 75 ml of watercontaining 5 grams of sodium hydroxide, and 75 ml of 10% sodiumhypochlorite solution were added simultaneously to 300 ml of concentratedammonium hydroxide which was cooled to 0°C, and vigorously stirred. During the addition the temperature was not allowed to rise above 5°C. The resultingsolid was recovered by filtration, washed thoroughly with water, and dried atroom temperature under reduced pressure. There was obtained 21 grams of6-ethoxybenzothiazole-2-sulfenamide melting at 132° to 155°C(decomposition). Recrystallization from ethyl acetate gave a product meltingat 140.5° to 143°C (decomposition).
Preparation of 6-Ethoxybenzothiazole-2-Sulfonamide: A solution of 3.39 grams(0.015 mol) of the sulfenamide in 100 ml of acetone was treated dropwise,with stirring, with a solution of 3.5 grams of potassium permanganate in 100ml of water. The temperature rose to 42°C. After stirring an additional 10minutes the reaction mixture was filtered to remove manganese dioxide, thelatter was washed with 100 ml of warm water, and the combined filtrates wereconcentrated under reduced pressure to remove acetone. The residual solutionwas treated with charcoal, filtered and acidified with concentrated hydrochloricacid. After standing in the refrigerator for 4 hours the solid sulfonamide wasrecovered by filtration, washed with water and dried. There was obtained 2.37grams of 6-ethoxybenzothiazole-2-sulfonamide melting at 180° to 190°C.Recrystallization from ethyl acetate-Skellysolve B gave 1.25 grams of materialmelting at 188° to 190.5°C. |
| Therapeutic Function | Diuretic, Cardiotonic, Smooth muscle relaxant, Respiratory stimulant |
| General Description | 6-Ethoxy-2-benzothiazolesulfonamide is a membrane permeable carbonic anhydrase inhibitor and its ocular disposition and pharmacology in normal albino rabbits has been investigated. It causes inhibition of insulin degradation in vitro. |
| Clinical Use | Ethoxzolamide is another carbonic anhydrase inhibitor with properties and uses resembling those of acetazolamide. |
6-ETHOXY-2-BENZOTHIAZOLESULFONAMIDE Preparation Products And Raw materials
| Raw materials | Ammonia-->6-ETHOXY-2-MERCAPTOBENZOTHIAZOLE-->Potassium permanganate-->Sodium hypochlorite |
