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| | 4-(Chlorosulfonyl)benzoic acid Basic information |
| | 4-(Chlorosulfonyl)benzoic acid Chemical Properties |
| Melting point | 230 °C | | Boiling point | 379.1±25.0 °C(Predicted) | | density | 1.5116 (estimate) | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | soluble in DMSO, Methanol | | pka | 3.09±0.10(Predicted) | | form | Powder | | color | Off-white to beige | | Water Solubility | Reacts with water. | | Sensitive | Moisture Sensitive | | InChI | 1S/C7H5ClO4S/c8-13(11,12)6-3-1-5(2-4-6)7(9)10/h1-4H,(H,9,10) | | InChIKey | PTCSSXYPZOFISK-UHFFFAOYSA-N | | SMILES | OC(=O)c1ccc(cc1)S(Cl)(=O)=O | | CAS DataBase Reference | 10130-89-9(CAS DataBase Reference) | | EPA Substance Registry System | Benzoic acid, 4-(chlorosulfonyl)- (10130-89-9) |
| Hazard Codes | C | | Risk Statements | 34-29-22 | | Safety Statements | 8-45-36/37/39-26 | | RIDADR | 3261 | | WGK Germany | 3 | | TSCA | TSCA listed | | HazardClass | 8 | | PackingGroup | II | | HS Code | 29173990 | | Storage Class | 8A - Combustible corrosive hazardous materials | | Hazard Classifications | Skin Corr. 1B |
| | 4-(Chlorosulfonyl)benzoic acid Usage And Synthesis |
| Chemical Properties | off-white to beige powder | | Uses | 4-(Chlorosulfonyl)benzoic acid was used in the preparation of polymer bound transfer hydrogenation catalyst and 4-(carboxymethyl-sulfamoyl)-benzoyladenosine. It was also used as a reagent in the sulfonation of γ-cyclodextrin. | | Synthesis | The general procedure for the synthesis of 4-(chlorosulfonyl)benzoic acid from 4-methylphenylsulfonic acid was as follows: a solution of potassium permanganate (KMnO4, 1.6 g) in water (H2O, 13 mL) was added slowly and dropwise at 80 °C to a solution of 4-methylphenylsulfonic acid (1.7 g, 10 mmol) and potassium hydroxide (KOH, 0.68 g, 12 mmol) in water (H2O, a 15 mL) solution. Upon completion of the reaction, the mixture was poured into ethanol (EtOH, 20 mL), filtered and concentrated to give potassium 4-carboxybenzenesulfonate (1.2 g). This intermediate was used directly in the next reaction without further purification. At room temperature, chlorosulfonic acid (4 mL) was slowly added dropwise to a stirring solution of potassium 4-carboxybenzenesulfonate (1.2 g). The reaction mixture was continued to be stirred for 2 hours and then poured into crushed ice. The resulting solid product was collected by filtration and washed with water (H2O) to give 4-(chlorosulfonyl)benzoic acid (0.22 g) as a white solid in 20% yield. The melting point of the product was 230-232 °C (literature value: 228-232 °C); 1H-NMR (CDCl3, 400 MHz) data: δ 8.30 (d, J=8.0 Hz, 2H), 8.42 (d, J=8.0 Hz, 2H). | | References | [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 2, p. 958 - 962 |
| | 4-(Chlorosulfonyl)benzoic acid Preparation Products And Raw materials |
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