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Chemical Structure| 121-61-9 Chemical Structure| 121-61-9
Chemical Structure| 121-61-9

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N-Acetylsulfanilamide is a sulfonamide derivative that exerts antibacterial activity by inhibiting bacterial dihydropteroate synthase (DHPS), thus preventing folate synthesis. It is commonly used to treat bacterial infections, particularly urinary tract infections, and to study mechanisms of antimicrobial resistance.

Synonyms: 4-Acetamidobenzenesulfonamide; APAS; NSC 406839

4.5 *For Research Use Only! Not for Human Use. We Do Not Sell to Patients.

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Product Details of N-Acetylsulfanilamide

CAS No. :121-61-9
Formula : C8H10N2O3S
M.W : 214.24
SMILES Code : CC(NC1=CC=C(S(=O)(N)=O)C=C1)=O
Synonyms :
4-Acetamidobenzenesulfonamide; APAS; NSC 406839
English Name :4-Acetamidobenzenesulfonamide
MDL No. :MFCD00035784
InChI Key :PKOFBDHYTMYVGJ-UHFFFAOYSA-N
Pubchem ID :8482

Safety of N-Acetylsulfanilamide

Application In Synthesis of N-Acetylsulfanilamide

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 121-61-9 ]

[ 121-61-9 ] Synthesis Path-Downstream   1~15

  • 1
  • [ 3034-53-5 ]
  • [ 121-61-9 ]
  • [ 127-76-4 ]
YieldReaction ConditionsOperation in experiment
With copper; potassium carbonate at 200℃;
  • 2
  • [ 13036-57-2 ]
  • [ 121-61-9 ]
  • [ 127-73-1 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate
  • 4
  • [ 22727-18-0 ]
  • [ 121-61-9 ]
  • [ 857622-48-1 ]
YieldReaction ConditionsOperation in experiment
With pyridine; copper; sodium carbonate
  • 5
  • [ 108-24-7 ]
  • [ 121-61-9 ]
  • [ 5626-90-4 ]
YieldReaction ConditionsOperation in experiment
95% In acetone at 30℃; for 6h; 3.1.2. Synthesis General procedure: Compound 1a (10 mmol) and anhydrous acetone (30 mL) in a round bottom flask, reacted with acetic anhydride (12 mmol) and ethyl chloroformate (15 mmol) at 30 °C for 6 h with stirring. Hydrochloric acid (1 M) was then added to the reaction mixture to adjust the pH to 1, the acetone removed by vacuum evaporation, and the aqueous phase was extracted with ethyl acetate (15 mL×3). Ethyl acetate phases were combined, washed twice with saturated NaCl solution, and dried with MgSO4. The extracte dethyl acetate solution was heated to 60 °C. Petroleum ether was added slowly to gradually produce a precipitate, transferred it to room temperature and cooled down, filtered and dried to obtain products 2a and 2b (Ghasemi et al. 2016; Dong et al. 2019; Wei et al. 2016). Compound 1b (10 mmol) and acetone (30 mL) reacted at 60 °C for 5 h. Product 2c was recrystallized with petroleum ether after the solvent was removed by evaporation under reduced pressure (Hebeisen et al. 2011). Compound 2c: 1H NMR (500 MHz, DMSO-d6, δ), 10.31 (s, 1H), 9.91 (s, 1H), 7.79- 7.71 (m, 4H), 2.08 (s, 3H), 1.77-1.78 (s, 6H).
95% In acetone at 30℃; for 6h; 3.1.2. Synthesis General procedure: Compound 1a (10 mmol) and anhydrous acetone (30 mL) in a round bottom flask, reacted with acetic anhydride (12 mmol) and ethyl chloroformate (15 mmol) at 30 °C for 6 h with stirring. Hydrochloric acid (1 M) was then added to the reaction mixture to adjust the pH to 1, the acetone removed by vacuum evaporation, and the aqueous phase was extracted with ethyl acetate (15 mL×3). Ethyl acetate phases were combined, washed twice with saturated NaCl solution, and dried with MgSO4. The extracte dethyl acetate solution was heated to 60 °C. Petroleum ether was added slowly to gradually produce a precipitate, transferred it to room temperature and cooled down, filtered and dried to obtain products 2a and 2b (Ghasemi et al. 2016; Dong et al. 2019; Wei et al. 2016). Compound 1b (10 mmol) and acetone (30 mL) reacted at 60 °C for 5 h. Product 2c was recrystallized with petroleum ether after the solvent was removed by evaporation under reduced pressure (Hebeisen et al. 2011). Compound 2c: 1H NMR (500 MHz, DMSO-d6, δ), 10.31 (s, 1H), 9.91 (s, 1H), 7.79- 7.71 (m, 4H), 2.08 (s, 3H), 1.77-1.78 (s, 6H).
93% With magnetic composite Fe3O4 Diatomite earth In tetrahydrofuran at 50℃; for 1h; General procedure for N-acylation of sulfonamides According to the Scheme 1, 4 mmol of N-(4-Sulfamoylphenyl) acetamide was treated with acetic anhydride (4 mmol) in glacial acetic acid (10 mL). The mixture was stirred at 50°C for the predetermined time. The progress of the reaction was monitored by TLC analysis. After the completion of the reaction, the precipitate was collected by filtration and washed with water. The impure precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration to afford N-(4-acetamidophenylsulfonyl)acetamide a1 as the white solid (0.97 g, 95%). The catalytic activities of different heterogeneous catalysts were determined by reactions performed in THF using a 1:1 molar ratio of sulfonamide to acetic anhydride or benzoyl chloride. In a typical route, N-(4-sulfamoylphenyl) acetamide (4 mmol) was treated with acetic anhydride (4 mmol) in the presence of catalyst (0.1 g) in THF (10 mL). After the appropriate time, the catalyst was separated with an external magnetic field, the solvent was evaporated by rotary evaporator. The precipitate was dissolved in aqueous solution of sodium carbonate (50 mL, pH=8.0) and filtered. Acetic acid was gently added to the liquor dropwise to precipitate the product (pH=5.0). The precipitate was collected by filtration and was washed with distilled water to afford N-(4-acetamidophenylsulfonyl)acetamide as the white solid (0.95 g, 93%).
With pyridine

  • 6
  • [ 539-03-7 ]
  • [ 121-61-9 ]
  • [ 16803-97-7 ]
YieldReaction ConditionsOperation in experiment
With Copper; potassium carbonate at 180℃; Erwaermen des Reaktionsprodukts mit wss. Natronlauge;
  • 7
  • [ 75-36-5 ]
  • [ 121-61-9 ]
  • [ 5626-90-4 ]
YieldReaction ConditionsOperation in experiment
With pyridine
  • 9
  • [ 103-88-8 ]
  • [ 121-61-9 ]
  • [ 16803-97-7 ]
YieldReaction ConditionsOperation in experiment
With Copper; potassium carbonate at 180℃; Erwaermen des Reaktionsprodukts mit wss. Natronlauge;
  • 10
  • [ 121-61-9 ]
  • [ 89641-65-6 ]
  • [ 92325-21-8 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In diphenylether Heating;
  • 12
  • [ 121-61-9 ]
  • [ 6101-31-1 ]
YieldReaction ConditionsOperation in experiment
99.5% With thionyl chloride In methanol for 2.5h; Reflux;
  • 13
  • [ 5626-90-4 ]
  • [ 121-61-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 4 h / 0 - 20 °C 2: hydrazine hydrate / ethanol / 1.5 h / 20 °C
  • 14
  • [ 95219-48-0 ]
  • [ 127-76-4 ]
  • [ 121-61-9 ]
YieldReaction ConditionsOperation in experiment
With ammonium hydroxide In water; acetone at 65℃; for 2.5h;
  • 15
  • [ 42017-89-0 ]
  • [ 121-61-9 ]
  • N-[4-(acetylamino)phenyl]sulfonyl}-2-[4–(4-chlorobenzoyl)phenoxy]-2-methylpropanamide [ No CAS ]
 

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