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| | 4-Hydrazinobenzene-1-sulfonamide hydrochloride Basic information |
| | 4-Hydrazinobenzene-1-sulfonamide hydrochloride Chemical Properties |
| Melting point | 149-152 °C(lit.) | | density | 1.644[at 20℃] | | storage temp. | under inert gas (nitrogen or Argon) at 2-8°C | | solubility | Methanol (Slightly, Heated), Water (Slightly) | | form | powder to crystal | | color | White to Light yellow to Light orange | | Water Solubility | Soluble in water. | | Sensitive | Hygroscopic | | Major Application | pharmaceutical (small molecule) | | InChI | InChI=1S/C6H9N3O2S.ClH/c7-9-5-1-3-6(4-2-5)12(8,10)11;/h1-4,9H,7H2,(H2,8,10,11);1H | | InChIKey | IKEURONJLPUALY-UHFFFAOYSA-N | | SMILES | C1(S(=O)(=O)N)C=CC(NN)=CC=1.Cl | | LogP | -0.99 at 20℃ | | CAS DataBase Reference | 17852-52-7(CAS DataBase Reference) | | EPA Substance Registry System | Benzenesulfonamide, 4-hydrazinyl-, hydrochloride (1:1) (17852-52-7) |
| Hazard Codes | Xn,Xi | | Risk Statements | 22-36/37/38 | | Safety Statements | 36-24/25 | | WGK Germany | 3 | | RTECS | DA9380000 | | Hazard Note | Irritant | | HS Code | 29350090 |
| | 4-Hydrazinobenzene-1-sulfonamide hydrochloride Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powde | | Uses | Intermediate in the production of Celebrex. | | Uses | It is a potentially useful intermediate in the production of Celebrex an anti inflammatory drug. | | Flammability and Explosibility | Non flammable | | Synthesis | The general procedure for the synthesis of p-hydrazinylbenzenesulfonamide hydrochloride from crystalline sulfanilamide was as follows: firstly, 4'-methylacetophenone was reacted with succinic anhydride in the presence of diisopropanolamine (LDA) and tetrahydrofuran (THF) for 1 hr at -78 °C to afford p-tolyl-4,6-dioxohexanoic acid in 66% yield and the product was a white solid. Subsequently, the sulfonamide was reacted with sodium nitrite (NaNO2) and concentrated hydrochloric acid for 30 min at 0-4 °C, followed by the addition of tin(II) chloride (SnCl2), and the reaction was continued for 4 h at 0 °C to produce 4-sulfonylaminophenylhydrazine hydrochloride in 55% yield, the product being a pale yellow solid. Finally, p-tolyl-4,6-dioxohexanoic acid was reacted with 4-sulfonylaminophenylhydrazine hydrochloride in a methanolic solution of triethanolamine (TEA) at room temperature for 16 h to give compound 30c, 3-[1-{p-(p-(sulfonylamino)phenyl}-5-p-tolyl-1H-pyrazol-3-yl]propanoic acid in 76% yield and the product was a yellow solid. | | References | [1] Journal of Medicinal Chemistry, 2007, vol. 50, # 18, p. 4444 - 4452
[2] Organic Letters, 2012, vol. 14, # 19, p. 5030 - 5033,4
[3] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 4, p. 913 - 922
[4] Patent: US2007/292352, 2007, A1. Location in patent: Page/Page column 45-46
[5] Patent: US2003/236294, 2003, A1. Location in patent: Page 9 |
| | 4-Hydrazinobenzene-1-sulfonamide hydrochloride Preparation Products And Raw materials |
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