3119-02-6

Basic information

• Product Name: 4-CYANOBENZENE-1-SULFONAMIDE
• Synonyms: 4-Sulphamoylbenzonitrile;4-Sulphamoylbenzonitrile, 4-(Aminosulphonyl)benzonitrile;p-cyano-benzenesulfonamid;BUTTPARK 48\11-02;4-CYANOBENZENESULFONAMIDE;4-CYANOBENZENE-1-SULFONAMIDE;4-CYANOBENZENE-1-SULPHONAMIDE;p-cyanobenzenesulphonamide
• CAS NO: 3119-02-6
• Molecular Formula: C₇H₆N₂O₂S
• Molecular Weight: 182.2
• EINECS: 221-492-5
• Product Categories: SULFONAMIDE
• Mol File: 3119-02-6.mol
• Article Data: 19

Chemical Properties

• Melting Point: 166 °C
• Boiling Point: 400.7 °C at 760 mmHg
• Flash Point: 196.2 °C
• Appearance: /
• Density: 1.3827 (rough estimate)
• Vapor Pressure: 1.24E-06mmHg at 25°C
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 9.57±0.10(Predicted)
• Water Solubility: 1.111g/L(15 oC)
• CAS DataBase Reference: 4-CYANOBENZENE-1-SULFONAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CYANOBENZENE-1-SULFONAMIDE(3119-02-6)
• EPA Substance Registry System: 4-CYANOBENZENE-1-SULFONAMIDE(3119-02-6)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38
• Safety Statements: 26-36/37/39-36/37
• RIDADR: 3276
• RTECS: DB1582000
• HazardClass: IRRITANT
• Hazardous Substances Data: 3119-02-6(Hazardous Substances Data)

Usage

Uses

4-Cyanobenzene-1-sulfonamide is a carbonic anhydrase inhibitor.

InChI:InChI=1/C7H6N2O2S/c8-5-6-1-3-7(4-2-6)12(9,10)11/h1-4H,(H2,9,10,11)

Synthetic route

p-cyanobenzenesulfonyl chloride (49584-26-1) → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
With ammonium hydroxide In tetrahydrofuran at 20℃; for 2h;	94%
With ammonium hydroxide In tetrahydrofuran at 0 - 5℃;	94%
With ammonium hydroxide In tetrahydrofuran; water at 0 - 20℃; for 1h;	88%

4-Chlorobenzenesulfonamide (98-64-6) + potassiumhexacyanoferrate(II) trihydrate → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
With C42H58NO3PPdS(2-); potassium acetate; tert-butyl XPhos In 1,4-dioxane; water at 100℃; for 1h; Inert atmosphere; Sealed tube;	91%

zinc(II) cyanide (557-21-1) + 4-Chlorobenzenesulfonamide (98-64-6) → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
Stage #1: zinc(II) cyanide With aluminum oxide; Ni(xantphos)(o-tolyl)Cl for 1h; Schlenk technique; Inert atmosphere; Sealed tube; Stage #2: 4-Chlorobenzenesulfonamide In 1-methyl-pyrrolidin-2-one at 20℃; for 24h; Schlenk technique; Inert atmosphere;	91%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 7h; Schlenk technique; Inert atmosphere; Sealed tube;	80%
With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 7h; Inert atmosphere; Sealed tube;	80%

4-cyanobenzenethiol (36801-01-1) → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
With manganese(IV) oxide; ammonia; oxygen In water; N,N-dimethyl-formamide at 90℃; under 7500.75 Torr; for 20h; Autoclave;	68%

potassium cyanide (151-50-8) + sulfanilamide (63-74-1) → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite at 0℃; for 0.166667h; Stage #2: potassium cyanide With copper(II) sulfate In water at 0 - 80℃; for 1h; Further stages.;	66%
Stage #1: sulfanilamide With hydrogenchloride; sodium nitrite Stage #2: potassium cyanide With copper(II) sulfate Sandmayer reaction;	53%

potassium cyanide + sulfanilamide (63-74-1) → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
With hydrogenchloride; copper(ll) sulfate pentahydrate; sodium nitrite In water at 0 - 80℃;	60%

4-Sulfamoyl-benzenediazonium (14289-29-3) + sodium cyanide (143-33-9) → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
With water; copper(II) sulfate
With water; nickel dichloride

4-(hydroxyimino-methyl)-benzenesulfonic acid amide (98276-92-7) + formamide (77287-34-4, 77287-35-5, 60100-09-6) → 4-cyanobenzenesulfonamide (3119-02-6)

4-(aminosulfonyl)-benzoic acid (138-41-0) → 4-cyanobenzenesulfonamide (3119-02-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: PCl5 / 60 °C / Erhitzen dann auf 110grad, 150grad und zuletzt auf 200grad 2: water; ammonia View Scheme

4-cyanobenzenesulfonamide (3119-02-6) → 4-homosulfanilamide (138-39-6)

Conditions	Yield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In methanol at 20℃; for 4h;	95%
With sodium methylate; nickel In methanol at 45℃; Product distribution; Further Variations:; Temperatures; current density; Electrochemical reaction;	85%
With ammonium hydroxide; hydrogen In tetrahydrofuran; methanol at 20℃; for 0.5h; Inert atmosphere;	82.2%

4-cyanobenzenesulfonamide (3119-02-6) → N'-hydroxy-4-sulfamoylbenzimidamide (4476-10-2)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Reflux;	93%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In ethanol for 6h; Reflux;	93%
With hydroxylamine In tetrahydrofuran; water at -25 - 20℃; for 16h;

4-cyanobenzenesulfonamide (3119-02-6) + tert-butyl 2-(acetoxymethyl)hepta-2,3-dienoate → tert-butyl (S)-1-((4-cyanophenyl)sulfonyl)-5-propyl-2,5-dihydro-1H-pyrrole-3-carboxylate

Conditions

Yield

Stage #1: 4-cyanobenzenesulfonamide With cyclopentyl methyl ether; (11R,13R)-11,13-dimethyl-12-phenyl-4,5,6,7,12,13-hexahydro-11H-diindeno[7,1-cd:1',7'-ef]phosphocine; sodium phenoxide In toluene at 20℃; for 0.0833333h; Inert atmosphere; Sealed tube; Stage #2: tert-butyl 2-(acetoxymethyl)hepta-2,3-dienoate In toluene at 40℃; for 24h; Reagent/catalyst; Inert atmosphere; Sealed tube; enantioselective reaction;

91%

methyl 2-octynoate (111-12-6) + 4-cyanobenzenesulfonamide (3119-02-6) → methyl (Z)-3-amino-2-(4-cyanophenyl)oct-2-enoate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Sealed tube;	91%

4-cyanobenzenesulfonamide (3119-02-6) + 2-chloro-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxylic acid → 2-chloro-N-(4-cyanophenyl)sulfonyl-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxamide

Conditions	Yield
Stage #1: 2-chloro-6-[3-[[1-(trifluoromethyl)cyclopropyl]methoxy]pyrazol-1-yl]pyridine-3-carboxylic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h; Stage #2: 4-cyanobenzenesulfonamide With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20℃; for 3h;	88%

4-cyanobenzenesulfonamide (3119-02-6) + 2-(1-phenylvinyl)-N-(pyridin-2-yl)benzamide → 4-cyano-N-((3-oxo-1-phenyl-2-(pyridin-2-yl)isoindolin-1-yl)methyl)benzenesulfonamide

Conditions	Yield
With [bis(acetoxy)iodo]benzene; sodium acetate; [Cp*Rh(MeCN)3][SbF6]2 In dichloromethane at 20℃; for 16h; Schlenk technique;	88%

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-cyanobenzenesulfonamide (3119-02-6) + ammonia (7664-41-7) + copper dichloride → C14H16CuN6O4S2 (1398545-79-3)

Conditions	Yield
In ethanol at 20℃;	80%

4-cyanobenzenesulfonamide (3119-02-6) + tert-butyl 2-isothiocyanato-4,5,6,7-tetrahydrobenzo[b]-thiophene-3-carboxylate (207743-78-0) → tert-butyl 2-(3-(4-cyanobenzenesulfonyl)thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate (1452776-83-8)

Conditions	Yield
With potassium carbonate In acetone for 20h; Reflux;	76%

4-cyanobenzenesulfonamide (3119-02-6) → 4-sulfamoylbenzoselenoamide

Conditions	Yield
With selenium; sodium tetrahydroborate In ethanol for 6h; Inert atmosphere; Reflux;	76%

succinic acid anhydride (108-30-5) + 4-cyanobenzenesulfonamide (3119-02-6) + methyl iodide (74-88-4) + ArgoGel-Rink-NH-Fmoc resin → 4-cyano-N-methylbenzenesulfonamide (56236-82-9)

Conditions	Yield
Multistep reaction.;	75%

2,3-dichloroquinoxaline (2213-63-0) + 4-cyanobenzenesulfonamide (3119-02-6) → N-(3-chloroquinoxalin-2-yl)-4-cyanobenzenesulfonamide

Conditions	Yield
With lithium hydroxide In N,N-dimethyl acetamide at 50℃; for 18h; Product distribution / selectivity;	73%

morpholine (110-91-8) + 4-cyanobenzenesulfonamide (3119-02-6) → (E)-4-cyano-N-(morpholinomethylene)benzenesulfonamide

Conditions	Yield
With copper(I) bromide In dimethyl sulfoxide at 100℃; for 24h; Schlenk technique; stereoselective reaction;	72%

4-cyanobenzenesulfonamide (3119-02-6) + 1-methyl-4-((3-methoxyphenyl)amino)-7-chloro-1H-indole-2-carboxylic acid → 1-methyl-4-((3-methoxyphenyl)amino)-7-chloro-N-(4-cyanophenylsulfonyl)-1H-indole-2-carboxamide

Conditions	Yield
With dmap; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; Inert atmosphere;	71.4%

4-cyanobenzenesulfonamide (3119-02-6) + 2-(prop-1-en-2-yl)-N-(pyridin-2-yl)benzamide → 4-cyano-N-((1-methyl-3-oxo-2-(pyridin-2-yl)isoindolin-1-yl)methyl)benzenesulfonamide

Conditions	Yield
With [bis(acetoxy)iodo]benzene; sodium acetate; [Cp*Rh(MeCN)3][SbF6]2 In dichloromethane at 20℃; for 16h; Schlenk technique;	71%

4-cyanobenzenesulfonamide (3119-02-6) → (E)-N'-hydroxy-4-sulfamoylbenzimidamide (1233243-50-9, 4476-10-2)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol at 75℃; for 6h;	70%
With hydroxylamine hydrochloride; sodium hydrogencarbonate In methanol at 75℃; for 6h;	70%

bis(1-methyl-1-phenylethyl)peroxide (80-43-3) + 4-cyanobenzenesulfonamide (3119-02-6) → 4-cyano-N-methylbenzenesulfonamide (56236-82-9)

Conditions	Yield
With copper acetylacetonate In acetone at 120℃; for 8h; Sealed tube;	70%

4-cyanobenzenesulfonamide (3119-02-6) → 4-cyanobenzenesulfonyl azide (1026020-39-2)

Conditions	Yield
With 3-azidosulfonyl-3H-imidazole-1-ium hydrogen sulfate; potassium carbonate In water; isopropyl alcohol at 20℃; for 18h;	68%

4-cyanobenzenesulfonamide (3119-02-6) + Benzoylformic acid (611-73-4) → N-((4-cyanophenyl)sulfonyl)-2-oxo-2-phenylacetamide

Conditions	Yield
Stage #1: Benzoylformic acid With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 3h; Inert atmosphere; Stage #2: 4-cyanobenzenesulfonamide With dmap; triethylamine In ethyl acetate; toluene at 0 - 20℃; for 18h; Inert atmosphere;	66%

N-[(E)-4-bromo-2-butenyl]-N-(tert-butyloxycarbonyl)-[3,4-bis(dodecyloxy)]benzenesulfonamide (861397-78-6) + 4-cyanobenzenesulfonamide (3119-02-6) → (E,E)-1,11-bis(tert-butyloxycarbonyl)-6-[(4-cyanophenyl)sulfonyl]-1,11-bis{[(3,4-didodecyloxy)phenyl]sulfonyl}-1,6,11-triazaundeca-3,8-diene (1453119-71-5)

Conditions	Yield
With potassium carbonate In acetonitrile for 24h; Reflux;	65%

Upstream product

• 14289-29-3 4-Sulfamoyl-benzenediazonium 
• 143-33-9 sodium cyanide 
• 98276-92-7 4-(hydroxyimino-methyl)-benzenesulfonic acid amide 
• 77287-34-4 formamide 
• 49584-26-1 p-cyanobenzenesulfonyl chloride 
• 151-50-8 potassium cyanide 
• 63-74-1 sulfanilamide 
• 138-41-0 4-(aminosulfonyl)-benzoic acid 
• 98-64-6 4-Chlorobenzenesulfonamide 
• 557-21-1 zinc(II) cyanide 
• 36801-01-1 4-cyanobenzenethiol 
• 10252-84-3 p-(tert.-Butylsulfamoyl)-benzonitril 

Downstream Products

• 56236-82-9 4-cyano-N-methylbenzenesulfonamide 
• 4476-10-2 N'-hydroxy-4-sulfamoylbenzimidamide 
• 1233243-50-9 (E)-N'-hydroxy-4-sulfamoylbenzimidamide 
• 1398545-79-3 C₁₄H₁₆CuN₆O₄S₂ 
• 1026020-39-2 4-cyanobenzenesulfonyl azide 
• 1452776-83-8 tert-butyl 2-(3-(4-cyanobenzenesulfonyl)thioureido)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate 
• 1453119-71-5 (E,E)-1,11-bis(tert-butyloxycarbonyl)-6-[(4-cyanophenyl)sulfonyl]-1,11-bis{[(3,4-didodecyloxy)phenyl]sulfonyl}-1,6,11-triazaundeca-3,8-diene 
• 1061091-52-8 N-[(4-cyanophenyl)sulfonyl]carbamic acid methyl ester 
• 4476-10-2 N′-hydroxy-4-sulfamoylbenzene-1-carboximidamide 
• 1233243-50-9 N-hydroxy-4-sulphamoyl-benzamidine 
• 162169-82-6 3-(α-cyclopropyl-meta-(4-cyanophenylsulfonylamino)benzyl)-6-(α-ethylphenethyl)-4-hydroxy-2H-pyran-2-one 

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