| Identification | Back Directory | [Name]
4-Fluoro-3-nitrobenzenesulfonamide | [CAS]
406233-31-6 | [Synonyms]
4-Fluoro-3-nitrobenzensulfonaMide
4-FLUORO-3-NITRO-BENZENESULFONAMIDE
4-Fluoro-3-nitrobenzenesulphonamide
4-fluoro-3-nitrobenzene-1-sulfonaMide
BenzenesulfonaMide, 4-fluoro-3-nitro-
2-Bromo-6-(2-methyl-1,3-dioxolane-2-yl)-pyridine | [Molecular Formula]
C6H5FN2O4S | [MDL Number]
MFCD08703185 | [MOL File]
406233-31-6.mol | [Molecular Weight]
220.178 |
| Chemical Properties | Back Directory | [Melting point ]
137.0 to 141.0 °C | [Boiling point ]
411.1±55.0 °C(Predicted) | [density ]
1.637 | [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Chloroform, Dimethylformamide, DMSO, Methanol | [form ]
Solid | [pka]
9.39±0.60(Predicted) | [color ]
Pale Yellow | [InChI]
InChI=1S/C6H5FN2O4S/c7-5-2-1-4(14(8,12)13)3-6(5)9(10)11/h1-3H,(H2,8,12,13) | [InChIKey]
FAYVDRRKPVJSPE-UHFFFAOYSA-N | [SMILES]
C1(S(N)(=O)=O)=CC=C(F)C([N+]([O-])=O)=C1 | [CAS DataBase Reference]
406233-31-6 |
| Hazard Information | Back Directory | [Chemical Properties]
Pale Yellow Solid | [Uses]
Reagent used to synthesize substituted arylsulfonamide derivatives | [Synthesis]
General procedure for the synthesis of 4-fluoro-3-nitrobenzenesulfonamide from 1-fluoro-2-nitrobenzene: 1-fluoro-2-nitrobenzene (4.0 g, 28.4 mmol) was dissolved in chlorosulfonic acid (25 mL), and the reaction was stirred at 120°C overnight. Upon completion of the reaction, it was cooled to room temperature and quenched by slow pouring into ice water. The reaction mixture was extracted with ethyl acetate (50 mL x 3), the organic layers were combined and concentrated under reduced pressure to remove the solvent. The crude product was redissolved in isopropanol and cooled to -60°C. At this temperature, ammonium hydroxide solution was added dropwise and stirring was continued for 1 hour. Subsequently, 6M hydrochloric acid (8 mL) was added to neutralize the reaction and the reaction mixture was warmed to room temperature and concentrated to dryness. The intermediate 4-fluoro-3-nitrobenzenesulfonamide (5.1 g, 82% yield) was finally obtained as a white solid.1H NMR (400 MHz, DMSO-d6) δ: 8.52 (dd, 1H), 8.20 (dq, 1H), 7.84 (dt, 1H), 7.73 (s, 2H). | [References]
[1] Patent: WO2017/123616, 2017, A1. Location in patent: Paragraph 00160
[2] Bioorganic and Medicinal Chemistry Letters, 2016, vol. 26, # 21, p. 5207 - 5211
[3] Chemistry - A European Journal, 2018, vol. 24, # 52, p. 13762 - 13766
[4] Journal of Medicinal Chemistry, 2006, vol. 49, # 3, p. 1165 - 1181
[5] Patent: US2011/237553, 2011, A1. Location in patent: Page/Page column 19 |
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