3240-35-5

Basic information

• Product Name: Benzenesulfonamide, 4-formyl- (9CI)
• Synonyms: Benzenesulfonamide, 4-formyl- (9CI);4-sulfamoylbenzaldehyde;benzenesulfonamide, 4-formyl-;4-methanoylbenzenesulfonamide
• CAS NO: 3240-35-5
• Molecular Formula: C₇H₇NO₃S
• Molecular Weight: 185.20038
• Product Categories: SULFONAMIDE
• Mol File: 3240-35-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 118-120 °C
• Boiling Point: 392.7 °C at 760 mmHg
• Flash Point: 191.3 °C
• Appearance: /
• Density: 1.424 g/cm³
• Vapor Pressure: 2.25E-06mmHg at 25°C
• Refractive Index: 1.594
• PKA: 9.76±0.10(Predicted)
• CAS DataBase Reference: Benzenesulfonamide, 4-formyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenesulfonamide, 4-formyl- (9CI)(3240-35-5)
• EPA Substance Registry System: Benzenesulfonamide, 4-formyl- (9CI)(3240-35-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 3240-35-5(Hazardous Substances Data)

Usage

Uses

4-Desaminomethyl 4-Formylmafenide is an impurity in the synthesis of Mafenide (M110200), an antibacterial.

InChI:InChI=1/C7H7NO3S/c8-12(10,11)7-3-1-6(5-9)2-4-7/h1-5H,(H2,8,10,11)

Synthetic route

4-cyanobenzenesulfonamide (3119-02-6) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With formic acid; aluminum nickel Stephen reduction;	86%
With hydrogenchloride; diethyl ether und anschliessenden Behandeln mit einer Loesung von Zinn(II)-chlorid und Chlorwasserstoff in Aether;
With formic acid; nickel for 1h; Heating;
With formic acid

4-(hydroxymethyl)benzenesulfonamide (67472-44-0) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With Dess-Martin periodane In acetonitrile at 80℃; for 2h;	83%
With dipyridinium dichromate In tetrahydrofuran for 2h; Molecular sieve;	55%
With pyridinium chlorochromate In dichloromethane; acetone	53%

(4-(N-acetylsulfamoyl)phenyl)methylene diacetate (796072-77-0) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With sulfuric acid In ethanol; water at 90℃; for 3h; Sealed tube;	80%

N-methoxy-N-methyl-(4-sulfamoyl)benzamide (179057-35-3) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20 - 50℃; for 7h; Reduction;	52%

4-[bis(acetyloxy)methyl]benzenesulfonamide (99856-72-1) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With sulfuric acid; water In methanol Reflux;	40%
With sulfuric acid In ethanol; water for 2h; Reflux;	12%
With hydrogenchloride
With sulfuric acid
Stage #1: 4-[bis(acetyloxy)methyl]benzenesulfonamide With ethanol; sulfuric acid; water for 2.5h; Heating / reflux; Stage #2: With potassium carbonate In water; ethyl acetate

N-methoxy-N-methyl-4-sulfonamidobenzamide → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With LiAlH4 In tetrahydrofuran; methanol; chloroform	16%

toluene-4-sulfonamide (70-55-3) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
Trennung durch Ueberfuehren in das Anil;
Multi-step reaction with 2 steps 1: chromium(III) oxide; sulfuric acid / acetic acid / 5 - 10 °C 2: sulfuric acid; water / methanol / Reflux View Scheme
Multi-step reaction with 2 steps 1: chromium(VI) oxide; sulfuric acid / 2.5 h / 0 - 5 °C 2: sulfuric acid / water; ethanol / 3 h / 90 °C / Sealed tube View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; chromium(VI) oxide / 4 h / 5 - 10 °C / Cooling with ice 2: sulfuric acid / water; ethanol / 2 h / Reflux View Scheme

N-<α,α-diacetoxy-toluene-sulfonyl-(4)>-acetamide → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With hydrogenchloride

N-<4-sulfamoyl-benzyl>-hexamethylenetetraminium chloride → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With acetic acid

toluene-4-sulfonamide (70-55-3) + sodium p-toluenesulfonic acid chloroamide → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With water

sulfanilamide (63-74-1) + docosen-(13c)-oyl chloride → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
Multi-step reaction with 2 steps 1.1: NaNO2; HCl 1.2: 53 percent / aq. CuSO4 2.1: 86 percent / Ni-Al; 75 percent aq. HCO2H View Scheme

4-(aminosulfonyl)-benzoic acid (138-41-0) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 73 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide / CH2Cl2 / 6 h / 20 °C 2: 52 percent / LiAlH4 / tetrahydrofuran / 7 h / 20 - 50 °C View Scheme
Multi-step reaction with 2 steps 1.1: diborane / tetrahydrofuran / 18.5 h / 0 - 20 °C 1.2: 1.5 h / 0 °C / Reflux 2.1: Dess-Martin periodane / acetonitrile / 2 h / 80 °C View Scheme

(4-(chlorosulfonyl)phenyl)methylene diacetate (69232-47-9) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: NH3 2: aqueous ethanol.H2SO4 View Scheme

p-toluenesulfonyl chloride (98-59-9) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2SO4; CrO3 2: NH3 3: aqueous ethanol.H2SO4 View Scheme

4-formylbenzene-1-sulfonyl chloride (85822-16-8) → 4-formyl-benzenesulfonamide (3240-35-5)

Conditions	Yield
With ammonia In tetrahydrofuran at 20℃; for 3h;
With ammonia In 1,4-dioxane; dichloromethane at 20℃; for 3h;

4-formyl-benzenesulfonamide (3240-35-5) + 1,3-diaminoguanidine hydrochloride (36062-19-8) → C15H17N7O4S2*ClH

Conditions	Yield
In ethanol for 16h; Reflux;	100%

4-formyl-benzenesulfonamide (3240-35-5) + 3-(3,4-difluorophenyl)-3-oxopropanenitrile (71682-97-8) → 4-(2-cyano-3-(3,4-difluorophenyl)-3-oxopropyl)benzenesulfonamide

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In ethanol at 60℃; for 0.5h;	98%

4-formyl-benzenesulfonamide (3240-35-5) + 5-chloro-2-methoxybenzoylhydrazide (33977-11-6) → C15H14ClN3O4S

Conditions	Yield
With acetic acid In ethanol for 15h; Reflux;	96%

4-formyl-benzenesulfonamide (3240-35-5) + 4-methylsulfanylaniline (104-96-1) → 4-methylthio-N-(4-sulfamoylbenzylidene)aniline

Conditions	Yield
	95%

4-formyl-benzenesulfonamide (3240-35-5) + Benzoylacetonitrile (614-16-4) → 4-(2-cyano-3-oxo-3-phenylpropyl)benzenesulfonamide

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In ethanol at 60℃; for 0.5h;	94%

4-formyl-benzenesulfonamide (3240-35-5) → 4-(hydroxymethyl)benzenesulfonamide (67472-44-0)

Conditions	Yield
With sodium tetrahydroborate In ethanol	92%

4-formyl-benzenesulfonamide (3240-35-5) + 6-amino-4-cyclopentylaminoquinoline-3-carbonitrile (915364-11-3) → 4-({[3-cyano-4-(cyclopentylamino)quinolin-6-yl]amino}methyl)benzenesulfonamide

Conditions	Yield
With sodium cyanoborohydride; acetic acid In ethanol at 25 - 30℃; pH=4;	86%

4-formyl-benzenesulfonamide (3240-35-5) + 4-methoxy-aniline (104-94-9) → 4-methoxy-N-(4-sulfamoylbenzylidene)aniline

Conditions	Yield
	85%
In methanol at 150℃; for 0.0833333h;	76%

4-formyl-benzenesulfonamide (3240-35-5) + N-Formylpiperidine (2591-86-8) → 4-formyl-N-[(E)-piperidin-1-ylmethylidene]benzenesulfonamide

Conditions	Yield
With oxalyl dichloride In dichloromethane at 0 - 20℃; for 3h;	84%

4-formyl-benzenesulfonamide (3240-35-5) + p-toluidine (106-49-0) → N-(4-sulfamoylbenzylidene)-4-methylaniline

Conditions	Yield
	82%
In methanol at 150℃; for 0.0833333h;	66%

4-formyl-benzenesulfonamide (3240-35-5) + 1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)quinolin-4(1H)-one-3-carboxylic acid-(2-thioxo-1,3-thiazolidin-4-one-3-yl)amide → 1-cyclopropyl-6-fluoro-7-(4-methylpiperazin-1-yl)quinolin-4(1H)-one-3-carboxylic acid-(2-sulfanylidene-5-p-sulfamoylphenylmethylidene-1,3-thiazolidin-4-one-3-yl)amide

Conditions	Yield
With sodium acetate; acetic acid for 12h; Reflux;	80.3%

4-formyl-benzenesulfonamide (3240-35-5) + C21H22FN5O4S2 → ofloxacin(5-p-sulfonamidobenzylidene-rhodanine-3-yl)amide

Conditions	Yield
With sodium acetate; acetic acid for 12h; Reflux;	78.2%

4-formyl-benzenesulfonamide (3240-35-5) + 3-([1,1'-biphenyl]-3-yl)-3-oxopropanenitrile → 4-(3-([1,1'-biphenyl]-3-yl)-2-cyano-3-oxopropyl)benzenesulfonamide

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; L-proline In ethanol at 60℃; for 0.5h;	78%

4-formyl-benzenesulfonamide (3240-35-5) + 5-bromo-2-indolin-2-one (20870-78-4) → (E)-5-bromo-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one (1261153-01-8)

Conditions	Yield
With sodium acetate In acetic acid for 4h; Knoevenagel condensation; Reflux;	77.8%

4-formyl-benzenesulfonamide (3240-35-5) + 3,4-dimethoxyaniline (6315-89-5) → C15H16N2O4S

Conditions	Yield
In methanol at 150℃; for 0.0833333h;	76%

4-formyl-benzenesulfonamide (3240-35-5) + 4-amino-phenol (123-30-8) → C13H12N2O3S

Conditions	Yield
In methanol at 150℃; for 0.0833333h;	75%

4-formyl-benzenesulfonamide (3240-35-5) + 4-chloro-aniline (106-47-8) → 4-chloro-N-(4-sulfamoylbenzylidene)aniline

Conditions	Yield
	72%

4-formyl-benzenesulfonamide (3240-35-5) + 4-fluoroaniline (371-40-4) → 4-fluoro-N-(4-sulfamoylbenzylidene)aniline

Conditions	Yield
In methanol at 150℃; for 0.0833333h;	72%
	25%

4-formyl-benzenesulfonamide (3240-35-5) + C21H23F2N5O3S2 → C28H28F2N6O5S3

Conditions	Yield
With sodium acetate; acetic acid for 12h; Reflux;	68%

4-formyl-benzenesulfonamide (3240-35-5) + tranylcypromine hydrochloride (1986-47-6, 2208-35-7, 2337-86-2, 4548-34-9, 37388-05-9, 54779-58-7, 61-81-4) → 4-((((1S*,2R*)-2-phenylcyclopropyl)amino)methyl)benzenesulfonamide

Conditions	Yield
Stage #1: 4-formyl-benzenesulfonamide; tranylcypromine hydrochloride With acetic acid In 1,2-dichloro-ethane at 20℃; for 2h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane	68%

4-formyl-benzenesulfonamide (3240-35-5) + 4-methoxycarbonyl aniline (619-45-4) → C15H14N2O4S

Conditions	Yield
In methanol at 150℃; for 0.0833333h;	65%

4-formyl-benzenesulfonamide (3240-35-5) + levofloxacin(rhodanine-3-yl)-amide → levofloxacin (2-thio-5-sulfonamidophenyl-2-methylidene-thiazolidin-4-one-3-yl)-amide

Conditions	Yield
With sodium acetate; acetic acid for 12h; Reflux;	64.5%

4-formyl-benzenesulfonamide (3240-35-5) + methyl 5-amino-2-hydroxybenzoate (42753-75-3) → C15H14N2O5S

Conditions	Yield
In methanol at 150℃; for 0.0833333h;	64%

4-formyl-benzenesulfonamide (3240-35-5) + 4-trifluoromethylphenylamine (455-14-1) → C14H11F3N2O2S

Conditions	Yield
In methanol at 150℃; for 0.0833333h;	63%

4-formyl-benzenesulfonamide (3240-35-5) + 5-fluoroindol-2(3H)-one (56341-41-4) → (E)-5-fluoro-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one (1261152-97-9)

Conditions	Yield
With sodium acetate In acetic acid for 4h; Knoevenagel condensation; Reflux;	62.9%

4-formyl-benzenesulfonamide (3240-35-5) + 5-nitrooxindole (20870-79-5) → (E)-5-nitro-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one (1261153-02-9)

Conditions	Yield
With sodium acetate In acetic acid for 4h; Knoevenagel condensation; Reflux;	62.3%

4-formyl-benzenesulfonamide (3240-35-5) + 3-(2,6-dimethylphenoxy)propylamine (57420-88-9) → 4-((3-(2,6-dimethylphenoxy)propylamino)methyl)benzenesulfonamide hydrochloride

Conditions	Yield
Stage #1: 4-formyl-benzenesulfonamide; 3-(2,6-dimethylphenoxy)propylamine In methanol at 20℃; Inert atmosphere; Stage #2: With sodium tetrahydroborate In methanol at 20℃; Inert atmosphere; Stage #3: With hydrogenchloride In methanol; water	62%

Upstream product

• 3119-02-6 4-cyanobenzenesulfonamide 
• 99856-72-1 4-[bis(acetyloxy)methyl]benzenesulfonamide 
• 70-55-3 toluene-4-sulfonamide 
• 179057-35-3 N-methoxy-N-methyl-(4-sulfamoyl)benzamide 
• 138-41-0 4-(aminosulfonyl)-benzoic acid 
• 796072-77-0 [4-(acetylsulfamoyl)phenyl]methanediyl diacetate 
• 85822-16-8 4-formylbenzene-1-sulfonyl chloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 69232-47-9 (4-(chlorosulfonyl)phenyl)methylene diacetate 
• 63-74-1 sulfanilamide 
• 67472-44-0 4-(hydroxymethyl)benzenesulfonamide 

Downstream Products

• 106273-71-6 isonicotinic acid-(4-sulfamoyl-benzylidenehydrazide) 
• 796072-77-0 [4-(acetylsulfamoyl)phenyl]methanediyl diacetate 
• 57840-60-5 2-(4-Aminosulfonylphenyl)-vinylcyclopropylketon 
• 179056-87-2 N-benzoyl-4-formylbenzenesulfonamide 
• 67472-44-0 4-(hydroxymethyl)benzenesulfonamide 
• 251086-10-9 N-tert-butyl-α-(4-aminosulfonylphenyl)nitrone 
• 1237750-32-1 C₆₉H₁₂N₂O₂S 
• 1261152-96-8 (E)-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 
• 1261152-99-1 (E)-5-methyl-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 
• 1261152-98-0 (E)-5-chloro-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 
• 1261153-01-8 (E)-5-bromo-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 
• 1261153-00-7 (E)-6-chloro-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 
• 1261152-97-9 (E)-5-fluoro-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 
• 1261153-02-9 (E)-5-nitro-3-[[4-(sulfamoyl)phenyl]methylene]indolin-2-one 

Relevant articles and documents

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