2-CHLOROBENZENESULFONAMIDE
2-Chlorobenzenesulfonamide
CAS: 6961-82-6
Molecular Formula: C6H6ClNO2S
2-CHLOROBENZENESULFONAMIDE - Names and Identifiers
| Name | 2-Chlorobenzenesulfonamide |
| Synonyms | 2-Chlorobenzenesulfamide 2-CHLOROBENZENESULFONAMIDE 2-Chlorobenzenesulfonamide o-Chlorobenzenesulfonamide 2-chloro-benzenedulfonamid 2-Chlorobenzenesulphonamide 2-CHLOROBENZENESULPHONAMIDE o-chlorobenzenesulphonamide Benzenesulfonamide, 2-chloro- Benzenesulfonamide, o-chloro- Benzenesulfonamide, 2-chloro- (9CI) |
| CAS | 6961-82-6 |
| EINECS | 230-156-7 |
| InChI | InChI=1/C6H6ClNO2S/c7-5-3-1-2-4-6(5)11(8,9)10/h1-4H,(H2,8,9,10) |
2-CHLOROBENZENESULFONAMIDE - Physico-chemical Properties
| Molecular Formula | C6H6ClNO2S |
| Molar Mass | 191.64 |
| Density | 1.408 (estimate) |
| Melting Point | 189-193°C(lit.) |
| Boling Point | 352.9±44.0 °C(Predicted) |
| Flash Point | 167.2°C |
| Water Solubility | 498.3mg/L(15 ºC) |
| Solubility | DMSO (Slightly), Methanol (Slightly) |
| Vapor Presure | 3.72E-05mmHg at 25°C |
| Appearance | Solid |
| Color | Off-White |
| BRN | 2937540 |
| pKa | 9.66±0.60(Predicted) |
| Storage Condition | Refrigerator |
| Refractive Index | 1.6000 (estimate) |
| Physical and Chemical Properties | Pure white crystals, industrial products for white powder, m.p.186 ~ 188 ℃, decomposition temperature of 210~270 ℃, insoluble in water, soluble in methanol and ethanol. |
2-CHLOROBENZENESULFONAMIDE - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| TSCA | Yes |
| HS Code | 29350090 |
| Hazard Class | IRRITANT |
2-CHLOROBENZENESULFONAMIDE - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| Use | O-chlorobenzene sulfonamide is an intermediate of the sulfonylurea herbicide chlorsulfuron-methyl. used as pesticide intermediate |
| production method | the preparation method is to add 30% hydrochloric acid in the reaction kettle, slowly Dropwise adding O-chloroaniline at about 10 ℃, after completion of the addition, the mixture was stirred for 10-20 min, and sodium nitrite solution was added dropwise at -5 ° C. Until the potassium iodide starch test paper turned blue, the dropwise addition was stopped, and the diazotization reaction was completed. Add dichloroethane in another reactor, a certain amount of sulfur dioxide gas at room temperature, and then add copper chloride and water in another reactor, the above diazo liquid and the dichloroethane solution of sulfur dioxide were slowly added into the reaction kettle under stirring at 15 ℃, the internal temperature was controlled at 20 ℃, the reaction was stirred strongly, and nitrogen was continuously released, after the addition was completed, stirring was continued until no nitrogen was released, and the reaction was continued at 50 ° C. For 80 min. After cooling, the dichloroethane layer was separated and concentrated to obtain a crude product of O-chlorobenzenesulfonyl chloride. Add 28% ammonia water in the ammoniating kettle, add the crude O-chlorobenzenesulfonyl chloride at 30~35 ℃, add, heat up to 45~50 ℃, react for 4~5H, cool, filter, wash with a small amount of water, the ortho-chlorobenzene sulfonamide was obtained by drying. Can also use sodium metabisulfite (or sodium sulfite) as sulfonating agent, in the reaction kettle to add 36% hydrochloric acid and copper sulfate, cooled to 0 ℃, the sodium metabisulfite is dissolved in water, at the same time, the diazo liquid prepared by the same method as the above-mentioned sulfur dioxide method is slowly added, the reaction temperature is controlled below 0 ℃, the two liquids are added at the same time, and the stirring is continued until no nitrogen is released, static separation of the oil layer, the crude O-chlorobenzene sulfonyl chloride amination, this step with the sulfur dioxide method, the same can be obtained O-chlorobenzene sulfonamide. The O-chlorobenzenesulfonyl chloride ether solution was slowly added dropwise to concentrated aqueous ammonia under stirring, reacted at 70 ° C. For 1H, filtered, dried and recrystallized to obtain O-chlorobenzene sulfonamide. |
Last Update：2024-04-09 21:11:58
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