5626-90-4

Basic information

• Product Name: N,N'-DIACETYLSULFANILAMIDE
• Synonyms: LABOTEST-BB LT00452432;N1,N4-DIACETYL SULPHANILAMIDE;N-(4-ACETYLSULFAMOYL-PHENYL)-ACETAMIDE;N,N'-DIACETYLSULFANILAMIDE;N,N-DIACETYLSULFANILAMIDE;N-[[4-(acetylamino)phenyl]sulphonyl]acetamide;N-[[4-(Acetylamino)phenyl]sulfonyl]acetamide;p-(Acetylamino)-N-acetylbenzenesulfonamide
• CAS NO: 5626-90-4
• Molecular Formula: C₁₀H₁₂N₂O₄S
• Molecular Weight: 256.28
• EINECS: 227-067-0
• Product Categories: CMLLYL
• Mol File: 5626-90-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.4049 (rough estimate)
• Refractive Index: 1.5650 (estimate)
• Water Solubility: 2.15g/L(37 oC)
• CAS DataBase Reference: N,N'-DIACETYLSULFANILAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: N,N'-DIACETYLSULFANILAMIDE(5626-90-4)
• EPA Substance Registry System: N,N'-DIACETYLSULFANILAMIDE(5626-90-4)

Safety Data

• Hazardous Substances Data: 5626-90-4(Hazardous Substances Data)

Usage

General Description

N,N'-DIACETYLSULFANILAMIDE is a chemical compound that is derived from sulfanilamide, a common antibiotic. It is synthesized by acetylating the amine groups of sulfanilamide, resulting in a compound with two acetyl groups attached to the nitrogen atoms. This modification is commonly used to increase the solubility and stability of the original compound. N,N'-DIACETYLSULFANILAMIDE has been studied for its potential as a drug and has been found to have antimicrobial properties. It is also used in various chemical reactions and as a reagent in organic synthesis. N,N'-DIACETYLSULFANILAMIDE is of interest to researchers and pharmaceutical companies for its potential applications in medicine and industry.

InChI:InChI=1/C10H12N2O4S/c1-7(13)11-9-3-5-10(6-4-9)17(15,16)12-8(2)14/h3-6H,1-2H3,(H,11,13)(H,12,14)

Synthetic route

acetic anhydride (108-24-7) + p-acetylaminobenzenesulfonamide (121-61-9) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

Conditions	Yield
With magnetic composite Fe3O4 Diatomite earth In tetrahydrofuran at 50℃; for 1h; Catalytic behavior; Reagent/catalyst; Temperature; Time; Solvent;	93%

sodium acetate (127-09-3) + sulfanilamide (63-74-1) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

Conditions	Yield
With acetic anhydride for 4h; Reflux;	77%

acetic anhydride (108-24-7) + sulfanilamide (63-74-1) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

Conditions	Yield
for 8h; Reflux;	70%
With pyridine

acetic anhydride (108-24-7) + sulfanilamide (63-74-1) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4) + sulphaacetamide (144-80-9)

Conditions	Yield
With sodium hydroxide In water at 75 - 85℃; for 0.25h; Acylation;	A 13% B 69%

acetic anhydride (108-24-7) + sulphaacetamide (144-80-9) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

Conditions	Yield
With pyridine for 1h; Reflux;	14.2%

N-mandeloyl-sulfanilic acid amide (4361-52-8) + acetic anhydride (108-24-7) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

Conditions	Yield
at 170℃;

acetic anhydride (108-24-7) + acetic acid (64-19-7) + sulfanilamide (63-74-1) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

acetyl chloride (75-36-5) + p-acetylaminobenzenesulfonamide (121-61-9) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

Conditions	Yield
With pyridine

Phenyl acetate (122-79-2) + p-acetylaminobenzenesulfonamide (121-61-9) → N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4)

N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4) + N-methyl-N-phenylformamide (93-61-8) → N-[4-({(E)-[methyl(phenyl)amino]methylidene}sulfamoyl)phenyl]acetamide

Conditions	Yield
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 4h;	83%

N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4) → sulphaacetamide (144-80-9)

Conditions	Yield
With sodium hydroxide for 2h; Reflux;	30%
With sodium hydroxide
With potassium hydroxide

N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4) + ethanolic KOH-solution → sulphaacetamide (144-80-9)

N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4) → p-acetylaminobenzenesulfonamide (121-61-9)

Conditions	Yield
Multi-step reaction with 2 steps 1: oxalyl dichloride / dichloromethane / 4 h / 0 - 20 °C 2: hydrazine hydrate / ethanol / 1.5 h / 20 °C View Scheme

N-acetyl-4-(acetamido)benzenesulfonamide (5626-90-4) → C11H13ClN2O4S

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydroxide / 2 h / Reflux 2: potassium carbonate / water / 2 h / 20 °C / Cooling with ice View Scheme

Upstream product

• 4361-52-8 N-mandeloyl-sulfanilic acid amide 
• 108-24-7 acetic anhydride 
• 64-19-7 acetic acid 
• 63-74-1 sulfanilamide 
• 121-61-9 p-acetylaminobenzenesulfonamide 
• 75-36-5 acetyl chloride 
• 122-79-2 Phenyl acetate 
• 144-80-9 sulphaacetamide 
• 127-09-3 sodium acetate 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 

Downstream Products

• 144-80-9 sulphaacetamide 
• 121-61-9 p-acetylaminobenzenesulfonamide 

Relevant articles and documents

Inhibition of carbonic anhydrase II by sulfonamide derivatives

A series of sulfonamide derivatives were synthesized, and the enzyme inhibitory activity of the synthesized compounds on carbonic anhydrase II was evaluated. Through molecular docking studies, it was found that compounds 1b, 1e, 2a, 2b, 3a have a strong binding affinity to carbonic anhydrase II. The IC50 values of the four compounds 1e, 2b, 3a, and 3b were lower than that of the positive control drug acetazolamide. What’s more, the compounds had a high inhibitory activity for A549 lung cancer cell growth, among them, 1e and 3a could inhibit both carbonic anhydrase II and lung cancer cell proliferation.

Catalytic activity of magnetic Fe3O4@Diatomite earth and acetic acid for the N-acylation of sulfonamides

The Br?nsted and Lewis acidic promoted N-acylation of sulfonamides with acetic anhydride or benzoyl chloride has been achieved using glacial acetic acid and magnetic Fe3O4@Diatomite earth. Use of acetic acid as solvent omits the need for organic bases and permits the isolation of products by filtration and precipitation. Additionally, the magnetic composite Fe3O4@Diatomite acts as a conjugate proton super acid, enabling the acylation of sulfonamide compounds.

Identification of a β1/β2-Specific Sulfonamide Proteasome Ligand by Crystallographic Screening

The proteasome represents a validated drug target for the treatment of cancer, however, new types of inhibitors are required to tackle the development of resistant tumors. Current fluorescence-based screening methods suffer from low sensitivity and are limited to the detection of ligands with conventional binding profiles. In response to these drawbacks, a crystallographic screening procedure for the discovery of agents with a novel mode of action was utilized. The optimized workflow was applied to the screening of a focused set of compounds, resulting in the discovery of a β1/β2-specific sulfonamide derivative that noncovalently binds between subunits β1 and β2. The binding pocket displays significant differences in size and polarity between the immuno- and constitutive proteasome. The identified ligand thus provides valuable insights for the future structure-based design of subtype-specific proteasome inhibitors.