Sulfanilamide is antibiotic against Gram positive becteria, Gram negative becteria, Chlamydia, working by blocking the synthesis of dihydrofolic acid by inhibiting the enzyme dihydropteroate synthase.

Synonyms: Sulphanilamide; 4-Aminobenzenesulfonamide; Gombardol

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Quality Control of Sulfanilamide Purity: 99% SDS Specification

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Product Details of Sulfanilamide

CAS No. :	63-74-1
Formula :	C₆H₈N₂O₂S
M.W :	172.20
SMILES Code :	O=S(C1=CC=C(N)C=C1)(N)=O
Synonyms :	Sulphanilamide; 4-Aminobenzenesulfonamide; Gombardol
MDL No. :	MFCD00007939
InChI Key :	FDDDEECHVMSUSB-UHFFFAOYSA-N
Pubchem ID :	5333

Safety of Sulfanilamide

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Sulfanilamide

* 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 [ 63-74-1 ]

[ 63-74-1 ] Synthesis Path-Downstream 1~33

1
[ 632-80-4 ]
[ 63-74-1 ]
[ 108988-44-9 ]

References: [1],1959,vol. 53,p. 199,213.

2
[ 17243-13-9 ]
[ 63-74-1 ]
[ 126884-27-3 ]

References: [1]Anales de la Real Sociedad Espanola de Fisica y Quimica,1947,vol. 43,p. 623,626.

3
[ 54589-54-7 ]
[ 63-74-1 ]
3-(4-sulfamoyl-anilinomethyl)-benzoic acid ethyl ester [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1950,vol. 70,p. 535.
Chem.Abstr.,1951,p. 6171.

4
[ 63-74-1 ]
[ 39150-45-3 ]

Yield	Reaction Conditions	Operation in experiment
62%	With hydrogen bromide; dihydrogen peroxide; at 20℃; for 5.0h;	Sulfanilamide (0.43g, 0.0025mol) was stirred in 15mL of 6N halogen acid (0.08mol) at room temperature, and 2mL of 30% hydrogen peroxide (0.02mol) was slowly added. After 5h, the product was filtered and recrystallized from ethanol. White solid. Yield: 62%. 1H NMR (DMSO-d6, 400MHz): delta 7.79 (s, 2H, ArH), 7.26 (s, 2H, SO2NH2), 6.11 (s, 2H, NH2). 13C NMR (DMSO-d6, 100MHz): delta 145.8, 132.7, 129.5, 106.1.
	With sodium perborate; hydrogen bromide; at 80 - 90℃;	To a mixture of 50.0 g sulfanilamide, 850 mL water and 200 mL 48% HBr solution, 90.0 g sodium perborate was added at 85 C. The mixture was stirred at 80-85 C for 30 min and then was cooled to room temperature and filtered. The residue was washed to be neutral by water. The solid was desulfonated by reacting with 70% sulfuric acid solution for 3 h under reflux. Crude product was obtained by steam distillation and further purified by recrystallization in ethanol. 1H NMR (500 MHz, CDCl3, delta in ppm): 7.35-7.40 (d, 2H, Ar-Hm), 6.5 (t, 1H, Ar-Hp).

References: [1]Green Chemistry,2011,vol. 13,p. 2187 - 2196.
[2]European Journal of Medicinal Chemistry,2016,vol. 124,p. 229 - 236.
[3]Analytical Chemistry,1984,vol. 56,p. 2157 - 2160.
[4]Organic Syntheses,1955,vol. Coll. Vol. III,p. 262.
[5]Gazzetta Chimica Italiana,1948,vol. 78,p. 275,280.
[6]Monatshefte fur Chemie,1915,vol. 36,p. 132.
[7]Archiv der Pharmazie,1943,vol. 281,p. 193,200.
[8]Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical,1989,vol. 28,p. 472 - 476.
[9]Journal of Molecular Catalysis A: Chemical,2014,vol. 390,p. 76 - 82.

5
[ 5319-77-7 ]
[ 594-42-3 ]
[ 63-74-1 ]
[ 69949-85-5 ]

References: [1]Journal of Pharmaceutical Sciences,1979,vol. 68,p. 182 - 185.

6
[ 10212-25-6 ]
[ 63-74-1 ]
[ 97626-01-2 ]

References: [1]Collection of Czechoslovak Chemical Communications,1985,vol. 50,p. 383 - 392.

7
[ 651-06-9 ]
[ 16290-93-0 ]
[ 63-74-1 ]
[ 13418-77-4 ]
[ 121-57-3 ]

References: [1]Pharmazie,1987,vol. 42,p. 511 - 513.

8
[ 97-08-5 ]
[ 63-74-1 ]
4-Chloro-3-nitro-N-(4-sulfamoyl-phenyl)-benzenesulfonamide [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,1999,vol. 34,p. 463 - 474.

9
[ 7726-95-6 ]
[ 64-19-7 ]
[ 63-74-1 ]
[ 39150-45-3 ]

References: [1]Monatshefte fur Chemie,1915,vol. 36,p. 132.

10
[ 62124-43-0 ]
[ 63-74-1 ]
4-(5-phenyl-oxazol-2-ylamino)-benzenesulfonamide [ No CAS ]

References: [1]Journal of Medicinal Chemistry,2005,vol. 48,p. 1610 - 1619.

11
[ 953039-63-9 ]
[ 63-74-1 ]
4-(8-bromo-6-fluoro-quinazolin-2-ylamino)benzensulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	In isopropyl alcohol; at 120℃; for 48.0h;	Step 6: 4-(8-Bromo-6-fluoroquinazolin-2-ylamino)benzensulfonamide; To a 0.4M suspension of <strong>[953039-63-9]8-bromo-2-chloro-6-fluoroquinazoline</strong>, 15-3 in isopropanol was added 4-aminobenzensulfonamide (1 eq). The reaction mixture was heated to 120 C. in an oil bath for 2 days. LCMS showed that reaction was complete under the condition. Ethyl acetate was added to the reaction flask and the suspension was stirred at ambient temperature for 30 min and was filtered. Filter cake was rinsed with hexane and dried in vacuum to give product in 81% yield. ES/MS m/z 397/399 (MH+).
81%	In isopropyl alcohol; at 120℃; for 48.0h;	Step 6. 4-(8-Bromo-6-fluoroqumazolin-2-ylarnino)benzensulfonamide To a 0.4M suspension of <strong>[953039-63-9]8-bromo-2-chloro-6-fluoroquinazoline</strong> in isopropanol was added 4- aminobenzensulfonamide (leq). The reaction mixture was heated to 120 0C in an oil bath for 2days. LCMS showed that reaction was complete under the condition. Ethyl acetate was added to the reaction flask and the suspension was stirred at ambient temperature for 30 min and was filtered. Filter cake was rinsed with hexane and dried in vacuum to give product in 81% yield. ES/MS m/z 397/399 (MH+).

References: [1]Patent: US2010/216767,2010,A1 .Location in patent: Page/Page column 82.
[2]Patent: WO2007/117607,2007,A2 .Location in patent: Page/Page column 332.

12
[ 872-50-4 ]
[ 765302-52-1 ]
[ 348-59-4 ]
[ 63-74-1 ]
2-[3-(2,5-dichloro-phenoxy)-4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydrogencarbonate; potassium carbonate; In water; ethyl acetate; acetone;	EXAMPLE 19 2-[3-(2,5-Dichloro-phenoxy)4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-19) step 1-To a solution of 12a (0.200 g; 0.960 mmol) and NMP (4 mL) was added K2CO3 (0.398 g; 2.88 mmol) and <strong>[348-59-4]1,4-dichloro-2-fluoro-benzene</strong> (0.124 mL; 1.056 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4) filtered and evaporated. The crude product was purified by SiO2 chromatography eluding with a gradient of hexane/EtOAc (100:0 to 60:40) to afford 142. steps 2 and 3-Hydrolysis and formation of the acid chloride were carried as described in step 7and 8 of Example 1 and used without additional purification. step 4-The acid chloride from step 3 (0.415 mmol) was dissolved in acetone (2 mL) and the flask and purged with nitrogen. NaHCO3 (0.070 g; 0.83 mmol) was added followed by 4-amino-benzenesulfonamide (0.072 g; 0.415 mmol) and water (4 mL). The mixture was sonicated for 5 min and allowed to stir for 12 h at RT. The reaction mixture was filtered and the crude product was washed sequentially with water and diethyl ether to afford I-19 Compound I-21 was prepared in the same manner except 4-amino-benzenesulfonamide was replaced with 2-chloro-phenylamine.

References: [1]Patent: US2005/239880,2005,A1 .

13
[ 872-50-4 ]
[ 765302-52-1 ]
[ 2268-05-5 ]
[ 63-74-1 ]
2-[3-(2,6-Dichloro-phenoxy)-4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydrogencarbonate; potassium carbonate; In water; ethyl acetate; acetone;	EXAMPLE 20 2-[3-(2,6-Dichloro-phenoxy)4-ethyl-phenyl]-N-(4-sulfamoyl-phenyl)-acetamide (I-20) step 1-To a solution of 12a (0.200 g; 0.960 mmol) and NMP (4 mL) was added K2CO3 (0.398 g; 2.88 mmol) and <strong>[2268-05-5]1,3-dichloro-2-fluoro-benzene</strong> (0.174 g; 1.056 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4) filtered and evaporated. The crude product was purified by SiO2 chromatography eluding with a hexane/EtOAc gradient (0 to 40% EtOAc) to afford 144. steps 2 and 3-Hydrolysis and formation of the acid chloride were carried as described in step 7and 8 of Example 1 and used without additional purification. step 4-The acid chloride from step 3 (0.14 mmol) was dissolved in acetone (2 mL) and the flask was purged with nitrogen. NaHCO3 (0.024 g; 0.28 mmol) was added followed by 4-amino-benzenesulfonamide (0.024 g; 0.14 mmol) and water (4 mL). The mixture was sonicated for 5 min and allowed to stir for 12 h at RT. The reaction mixture was filtered and the crude product was washed sequentially with water and diethyl ether to afford I-20. Compound I-23 was prepared in the same manner except 4-amino-benzenesulfonamide was replaced by 2-chloro-phenylamine.

References: [1]Patent: US2005/239880,2005,A1 .

14
[ 63-74-1 ]
docosen-(13<i>c</i>)-oyl chloride [ No CAS ]
[ 40724-47-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2002,vol. 12,p. 1013 - 1015.

15
ammonium chloride [ No CAS ]
[ 63-74-1 ]
[ 77-78-1 ]
[ 1709-59-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In methanol;	Step 1 [(4-Aminophenyl)sulfonyl]dimethylamine To a solution of 40.2 g of sulfanilamide in 1.5 L of MeOH cooled at 0 C., 220 mL of dimethylsulfate and 464 mL of NaOH 5N were added simultanously via two syringe pumps over a period of 3 h. After consumption of the starting material, the organic solvent was removed under vacuum, aqueous NH4Cl was added and the product was extracted with EtOAc. The organic layer was washed with water, brine and dried over anhydrous Na2SO4. The organic phase was concentrated to dryness and the crude solid was recrystallized from 90% EtOAc in hexanes to give 26.2 g of the title compound as a white solid. 1H NMR (CDCl3) delta7.53 (2H, d), 6.69 (2H, d) 4.12 (2H, br s), 2.64 (6H, s).

References: [1]Patent: US6410583,2002,B1 .

16
[ 5654-97-7 ]
[ 63-74-1 ]
[ 36805-97-7 ]
[ 295327-24-1 ]

Yield	Reaction Conditions	Operation in experiment
36 mg (21%)	With methanesulfonic acid; sodium hydrogencarbonate; In methanol; ethanol; water; N,N-dimethyl-formamide;	Example 3A 4-[(2-Oxo-1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)methyl]amino}benzenesulfonamide Dimethylformamide di-tert-butyl acetal (180 mg, 0.89 mmol) was added to a solution of 1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-2-one (70 mg, 0.52 mmol) in 0.25 ml DMF, and the reaction mixture was slowly warmed to 100 C. The cooled solution was then diluted with 5 ml of ethanol. Sulfanilamide (172 mg, 1.00 mmol) and methanesulfonic acid (60 mg, 0.63 mmol) were added, and the reaction mixture was stirred at reflux for 2 hours. The cooled solution was diluted with 4 ml of water, treated with NaHCO3 (70 mg, 0.83 mmol) and stirred 10 min. The resulting solid was filtered, washed with water and ethanol, and then suspended in boiling methanol and filtered upon cooling. Inorganics were removed by filtration through a short silica gel column, eluding with DMF. The resulting solution was diluted with an equal volume of ice water, and the suspension was refrigerated overnight. The solid was isolated by filtration and dried to give 36 mg (21%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) (4:1 ratio of Z:E isomers): delta (Z) 11.07 (s, 1H), 10.76 (d, J=12.4 Hz, 1H), 8.67 (d, J=12.5 Hz, 1H), 7.92 (d, J=5.1 Hz, 1H), 7.84 (d, J=7.3 Hz,
36 mg (21%)	With methanesulfonic acid; sodium hydrogencarbonate; In methanol; ethanol; water; N,N-dimethyl-formamide;	EXAMPLE 3 4-[(2-oxo-1,2-Dihydro-3H-pyrrolo[2,3-b]pyridin-3-ylidene)methyl]amino}benzenesulfonamide Dimethylformamide di-tert-butyl acetal (180 mg, 0.89 mmol) was added to a solution of 1,2-dihydro-3H-pyrrolo[2,3-b]pyridin-2-one (70 mg, 0.52 mmol) in 0.25 ml DMF, and the reaction mixture was slowly warmed to 100 C. The cooled solution was then diluted with 5 ml of ethanol. Sulfanilamide (172 mg, 1.00 mmol) and methanesulfonic acid (60 mg, 0.63 mmol) were added, and the reaction mixture was stirred at reflux for 2 h. The cooled solution was diluted with 4 ml of water, treated with NaHCO3 (70 mg, 0.83 mmol) and stirred 10 min. The resulting solid was filtered, washed with water and ethanol, and then suspended in boiling methanol and filtered upon cooling. Inorganics were removed by filtration through a short silica gel column, eluding with DMF. The resulting solution was diluted with an equal volume of ice water, and the suspension was refrigerated overnight. The solid was isolated by filtration and dried to give 36 mg (21%) of the title compound as a yellow solid: 1H NMR (400 MHz, DMSO-d6) (4:1 ratio of Z:E isomers): delta (Z) 11.07 (s, 1H), 10.76 (d, J=12.4 Hz, 1H), 8.67 (d, J=12.5 Hz, 1H), 7.92 (d, J=5.1 Hz, 1H), 7.84 (d, J=7.3 Hz, 1H), 7.77 (d, J=8.7 Hz, 2H), 7.55 (d, J=8.6 Hz, 2H), 7.25 (s, 2H), 6.93 (dd, J=7.3, 5.1 Hz, 1H); (E) 10.79 (s, 1H), 9.70 (d, J=13.4 Hz, 1H), 8.23 (d, J=7.3 Hz, 1H). ESI-MS m/z 315 (M-H). Anal. Calcd. for C14H12N4O3S. 0.5 H2O: C, 51.68; H, 4.03; N, 17.03. Found: C, 51.75; H, 3.95; N, 17.26.

References: [1]Patent: US6369086,2002,B1 .
[2]Patent: US6624171,2003,B1 .

17
[ 4903-09-7 ]
[ 63-74-1 ]
N-(3-chloro-4-methoxybenzylidene)-4-sulfamoylaniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%		79(i) N-(3-Chloro-4-methoxybenzylidene)-4-sulfamoylaniline Following a procedure similar to that described in Example 1(i), but using <strong>[4903-09-7]3-chloro-4-methoxybenzaldehyde</strong> and 4-sulfamoylaniline as starting materials, the title compound was obtained as a pale yellow powder (yield 72percent). Nuclear Magnetic Resonance Spectrum (270 MHz, hexadeuterated dimethyl sulfoxide) delta ppm: 8.37 (1H, singlet); 8.00 (1H, doublet, J=2 Hz); 7.93 (2H, doublet, J=9 Hz); 7.77 (1H, doublet of doublets, J=2 and 9 Hz); 7.24 (2H, doublet, J=9 Hz); 7.09 (1H, doublet, J=9 Hz); 6.90 (2H, broad doublet, J=5 Hz); 3.99 (3H, singlet).

References: [1]Patent: US5908858,1999,A .

18
[ 63-74-1 ]
[ 21286-54-4 ]
[ 1286246-03-4 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃;Inert atmosphere;	General procedure: Reactions of (1R)-(-)-10-camphorsulfonyl chloride 1 and (1S)-(+)-10-camphorsulfonyl chloride 2 (0.3 g,1.0 equiv) with amino derivatives 3 - 7 (1.0 equiv) were carried out at 0 C to room temperature in Schotten-Baumann conditions under nitrogen atmosphere, in the presence of a stoichiometric amount of dropwised dry TEA (1.0 equiv for 3, 5, 6 and 2.0 equiv for 4, 7), in dry DMF as solvent (2 ml). When complete (monitoring by TLC), reactions were quenched with crushed ice, extracted with ethyl acetate (20 ml), washed with 1 N HCl (2 x 10 ml) and brine (2 x 10 ml). The collected organic phase was dried on anhydrous Na2SO4, filtered and evaporated under vacuum. The crude was purified by silica gel column chromatography eluting with n-hexane/ethyl acetate or DCM/methanol to afford compounds 8-17 as white solids in medium yields.

References: [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1334 - 1337.

19
[ 32703-79-0 ]
[ 63-74-1 ]
[ 1429784-76-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2601 - 2605.

20
[ 17823-69-7 ]
[ 63-74-1 ]
[ 1456732-88-9 ]

Yield	Reaction Conditions	Operation in experiment
		Dissolved 0.500 g <strong>[17823-69-7]2-cyano-3,3-bis(methylthio)acrylamide</strong> in 15 mL EtOH and added Sulfanilamide (1.0 eq.) . Stirred reaction at 75 C until starting amide was absent by HPLC. Once complete (18 hrs), reaction was brought to room temperature and filtered to obtain a light yellow powder as product. Product was allowed to dry under vacuum for 1 hr. Product was then suspended in 10 mL EtOH and hydrazine hydrate (1 eq.) was added dropwise. Reaction was heated at 75 C until intermediate was absent (HPLC). Once intermediate was absent (18 hrs), reaction was brought to room temperature and filtered to obtain 5-amino-3-((4-sulfamoylphenyl)amino)-lH-pyrazole-4-carboxamide as a yellow powder. Product was allowed to dry under vacuum for 1 hr. 5-amino-3-((4-sulfamoylphenyl)amino)-lH-pyrazole-4-carboxamide

References: [1]Patent: WO2013/138613,2013,A1 .Location in patent: Paragraph 00440.

21
[ 444731-75-3 ]
[ 63-74-1 ]
[ 1572439-04-3 ]