138-38-5

Basic information

• Product Name: 4-Ethylbenzenesulfonamide
• Synonyms: Methylbutadiyne;Methyldiacetylene;Penta-1,3-diyne;BenzenesulfonaMide, 4-ethyl-;4-ethylbenzenesulfonamide;4-ETHYLBENZENESULPHONAMIDE;P-ETHYLBENZENESULFONAMIDE;Benzenesulfonamide, 4-ethyl- (9CI)
• CAS NO: 138-38-5
• Molecular Formula: C₈H₁₁NO₂S
• Molecular Weight: 185.24
• EINECS: 1308068-626-2
• Product Categories: SULFONAMIDE
• Mol File: 138-38-5.mol
• Article Data: 14

Chemical Properties

• Melting Point: 111 °C
• Boiling Point: 329.658 °C at 760 mmHg
• Flash Point: 153.172 °C
• Appearance: /
• Density: 1.225 g/cm³
• Vapor Pressure: 0.000175mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.19±0.10(Predicted)
• CAS DataBase Reference: 4-Ethylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Ethylbenzenesulfonamide(138-38-5)
• EPA Substance Registry System: 4-Ethylbenzenesulfonamide(138-38-5)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 138-38-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C8H11NO2S/c1-2-7-3-5-8(6-4-7)12(9,10)11/h3-6H,2H2,1H3,(H2,9,10,11)

Synthetic route

triethyl borane (97-94-9) + 4-bromo-benzenesulfonic acid amide (701-34-8) → 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran Suzuki coupling; Inert atmosphere; Reflux; chemoselective reaction;	88%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In tetrahydrofuran Suzuki-Miyaura cross-coupling; Inert atmosphere; Reflux;	88%

4-Ethyl-N-isopropylidene-benzenesulfonamide (110955-51-6) → 4-ethylbenzenesulfonamide (138-38-5) + acetone (67-64-1)

Conditions	Yield
With water for 1h; Heating;	A 77% B n/a

1-Ethyl-3-trimethylsilylbenzol (17988-51-1) → 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
With chlorure d'aluminium; chlorure de sulfamoyle In dichloromethane for 15h; Ambient temperature;	38%

p-ethylbenzenesulfonyl chloride (16712-69-9) → 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
With ammonia at 20 - 100℃;	9.5%
With ammonia
With ammonium hydroxide at 40℃; for 0.5h;
With ammonium hydroxide for 2h; Large scale;	450 kg
With pyridine; ammonium hydroxide In dichloromethane at 0 - 20℃; for 4h;

ethylbenzene (100-41-4) → 4,4'-sulfonylbis(1-ethylbenzene) (66294-51-7) + 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
With chlorosulphuric acid; chloroform Erwaermen des Reaktionsprodukts mit Ammoniumcarbonat;

1-ethyl-benzene-sulfonyl fluoride-(4) → 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
With ammonia

N-chloro-N-sodio-p-ethylbenzenesulfonamide → 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
With sodium hydroxide; D-Fructose In water at 29.85℃; Kinetics; Further Variations:; pH-values; Reagents; ionic strength values;

2-Ethyl-1,4-bis-trimethylsilanyl-benzene (128254-32-0) → 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
Multi-step reaction with 2 steps 1: 100 percent / acide trifluoroacetique / CCl4 / 15 h / Heating 2: 38 percent / chlorure d'aluminium, chlorure de sulfamoyle / CH2Cl2 / 15 h / Ambient temperature View Scheme

ammonium hydroxide (1336-21-6) + p-ethylbenzenesulfonyl chloride (16712-69-9) → 4-ethylbenzenesulfonamide (138-38-5)

Conditions	Yield
With sulfuric acid; trichlorophosphate In ethylbenzene; water

4-ethylbenzenesulfonamide (138-38-5) + [1,1'-biphenyl]-2,2'-iodonium trifluoromethanesulfonate (189999-35-7) → 9-((4-ethylphenyl)sulfonyl)-9H-carbazole (1469876-05-8)

Conditions	Yield
With copper diacetate; sodium carbonate In ethylene glycol; isopropyl alcohol at 90℃; for 16h; Inert atmosphere;	100%
With copper diacetate; sodium carbonate; ethylene glycol In isopropyl alcohol at 85℃; for 16h; Ullmann Condensation; Inert atmosphere;	74%

4-ethylbenzenesulfonamide (138-38-5) + p-chlorphenylisocyanate (104-12-1) → N-([(4-chlorophenyl)amino]carbonyl)-4-ethylbenzenesulfonamide (102607-92-1)

Conditions	Yield
With sodium hydroxide In acetone	92%

4-ethylbenzenesulfonamide (138-38-5) + triethylamine (121-44-8) → (E)-N,N-diethyl-N'-((4-ethylphenyl)sulfonyl)formimidamide

Conditions	Yield
With N-Bromosuccinimide; 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 25℃; for 4h; Darkness;	91%

1,1-Diphenylmethanol (91-01-0) + 4-ethylbenzenesulfonamide (138-38-5) → benzhydryl ether (574-42-5) + C21H21NO2S

Conditions	Yield
With acidic mesoporous zeolite β-catalyst In 1,2-dichloro-ethane at 80℃; for 6h; Inert atmosphere;	A n/a B 91%

morpholine (110-91-8) + 4-ethylbenzenesulfonamide (138-38-5) → (E)-4-ethyl-N-(morpholinomethylene)benzenesulfonamide

Conditions	Yield
With copper(I) bromide In dimethyl sulfoxide at 100℃; for 24h; Schlenk technique; stereoselective reaction;	91%

4-ethylbiphenyl (5707-44-8) + 4-ethylbenzenesulfonamide (138-38-5) → N-(1-([1,1'-biphenyl]-4-yl)ethyl)-4-ethylbenzenesulfonamide

Conditions	Yield
With tetrabutylammonium tetrafluoroborate In 1,2-dichloro-ethane at 20℃; for 2.5h; Electrochemical reaction; Inert atmosphere; regioselective reaction;	84%

4-ethylbenzenesulfonamide (138-38-5) + cyclohexanone (108-94-1) → 4-Ethylbenzolsulfanilid (64329-90-4)

Conditions	Yield
With 1,10-Phenanthroline; palladium(II) trifluoroacetate; oxygen In toluene at 140℃; for 40h;	79%

p-ethylbenzenesulfonyl chloride (16712-69-9) + 4-ethylbenzenesulfonamide (138-38-5) → 4-ethyl-N-[(4-ethylphenyl)sulfonyl]benzenesulfonamide

Conditions	Yield
With dmap; triethylamine In toluene at 70℃; for 12h;	79%

4-ethylbenzenesulfonamide (138-38-5) + (3R,4S)-1-(4-methylphenyl)-3-(3-p-toluenesulfonate-n-propyl)-4-(4-nitrophenyl)-2-azetidinone → (3R,4S)-1-(4-methylphenyl)-3-[3-(4-ethylbenzenesulfonamido)propyl]-4-(4-nitrophenyl)-2-azetidinone

Conditions	Yield
With potassium carbonate In acetonitrile at 90℃; for 12h;	78%

Togni's reagent II (887144-94-7) + 4-ethylbenzenesulfonamide (138-38-5) → C9H10F3NO2S

Conditions	Yield
With sodium decatungstate; sulfuric acid; copper dichloride In water; acetonitrile at 20 - 30℃; for 12h; Irradiation; regioselective reaction;	77%

4-ethylbenzenesulfonamide (138-38-5) + dimethyl sulfoxide (67-68-5) + Eudesmic acid (118-41-2) → 4,5,6-trimethoxy-2-(4-ethylphenylsulfonyl)isoindoline-1-one

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In chlorobenzene at 110℃; for 12h; Pummerer Sulfoxide Rearrangement; Inert atmosphere;	73%

4-ethylbenzenesulfonamide (138-38-5) + tert-butyldimethylsilyl chloride (18162-48-6) → N-(tert-butyldimethylsilyl)-4-ethylbenzene-1-sulfonamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 18h;	71.8%

4-ethylbenzenesulfonamide (138-38-5) + (1R,2R,4S,5S,6R)-6-Bromomethyl-3-oxa-tricyclo[3.2.1.02,4]octane → (1R,2S,3S,6S,7R)-4-(4-Ethyl-benzenesulfonyl)-4-aza-tricyclo[4.2.1.03,7]nonan-2-ol

Conditions	Yield
With tetrabutylammomium bromide; potassium carbonate In benzene for 1h; Heating;	70%

4-bromo-2-trifluoromethyl-aniline (445-02-3) + 4-ethylbenzenesulfonamide (138-38-5) → N-(4-amino-3-(trifluoromethyl)phenyl)-4-ethylbenzenesulfonamide

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine at 70℃; for 20h;	46%
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine at 70℃; for 20h;

4-ethylbenzenesulfonamide (138-38-5) + N-(1-(2-((2-methoxy-4-methylphenyl)sulfonamido)-1-(3-methoxyphenyl)-2-oxoethyl)indolin-4-yl)-N-((4-methoxyphenyl)sulfonyl)glycine → 2-(4-((N-(2-((4-ethylphenyl)sulfonamido)-2-oxoethyl)-4-methoxyphenyl)sulfonamido)indolin-1-yl)-N-((2-methoxy-4-methylphenyl)sulfonyl)-2-(3-methoxyphenyl)acetamide

Conditions	Yield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 40℃; for 4h;	45%

4-ethylbenzenesulfonamide (138-38-5) + Cyclohexyl isocyanate (3173-53-3) → DK37 (965-82-2)

Conditions	Yield
Stage #1: 4-ethylbenzenesulfonamide With potassium carbonate In acetone for 1.5h; Heating; Stage #2: Cyclohexyl isocyanate for 16h; Heating;	29.9%

9-hydroxyxanthene (90-46-0) + 4-ethylbenzenesulfonamide (138-38-5) → 4-ethyl-benzenesulfonic acid xanthen-9-ylamide

Conditions	Yield
With acetic acid

4-ethylbenzenesulfonamide (138-38-5) → 4-acetylbenzenesulfonamide (1565-17-9)

Conditions	Yield
With magnesium(II) nitrate; potassium permanganate; acetone
With chromium(VI) oxide; acetic acid for 3h; Ambient temperature; Yield given;

4-ethylbenzenesulfonamide (138-38-5) + acrylonitrile (107-13-1) → 4-ethyl-benzenesulfonic acid-[bis-(2-cyano-ethyl)-amide] (100720-12-5)

Conditions	Yield
With N-benzyl-trimethylammonium hydroxide

4-ethylbenzenesulfonamide (138-38-5) + orthoformic acid triethyl ester (122-51-0) → ethyl N-p-ethylbenzene-sulphonyl-formimidate (100981-70-2)

Conditions	Yield
at 110℃; for 2h;

cis,trans-2,5-dimethoxytetrahydrofuran (696-59-3) + 4-ethylbenzenesulfonamide (138-38-5) → 1-(4-Ethyl-benzenesulfonyl)-1H-pyrrole (891392-78-2)

Conditions	Yield
With acetic acid

Upstream product

• 138384-97-1 METHYL 4-((4-(TERT-BUTOXYCARBONYL)PIPERAZINYL)SULFONYL)BENZOATE 
• 13838-47-6 7-AMINO-5-METHOXYINDOLE 
• 138384-68-6 METESIND 
• 13838-45-4 5-METHOXY-7-NITRO-2-INDOLECARBOXYLIC ACID 
• 138384-42-6 N(6)-(4-(piperazinylsulfonyl)benzyl)-6-aminobenz(cd)indol-2(1H)-one 
• 1383842-58-7 ethyl 4-chlorobenzofuran-2-carboxylate 
• 13838-34-1 2,4-dichloro-6-(4-methylphenoxy)-1,3,5-triazine 
• 13838-32-9 2-BUTOXY-4,6-DICHLORO-1,3,5-TRIAZINE 
• 13838-29-4 4-chloro-6-phenoxy-N-phenyl-1,3,5-triazin-2-amine 
• 1383824-12-1 Methyl 2,4-dibroMobenzo[d]thiazole-6-carboxylate 
• 138381-83-6 (2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid PhenylMethyl Ester 
• 13838-16-9 2-CHLORO-1,1,2-TRIFLUOROETHYL DIFLUOROMETHYL ETHER 
• 1383816-29-2 Tropifexor 
• 13838-14-7 Diphenazine 

Downstream Products

• 138385-00-9 4-((4-(TERT-BUTOXYCARBONYL)PIPERAZINYL)SULFONYL)BENZOIC ACID 
• 138385-04-3 4-([4-(BROMOMETHYL)PHENYL]SULPHONYL)MORPHOLINE 
• 138385-29-2 3-(1-deoxyribofuranosyl)benzamide 
• 1383854-81-6 (S)-6-FLUORO-INDAN-1-YLAMINE 
• 138385-59-8 2,6-DIMETHYL-4-IODOANILINE 
• 138385-69-0 1-Oxa-2-azaspiro[2.5]octane, 2-acetyl-5-methyl-, (3R-cis)- (9CI) 
• 13838-59-0 3-acetyl-5-benzoyl-6-methyl-2H-pyran-2,4(3H)-dione 
• 138386-62-6 Benzenamine, 2-(1,3-butadienyl)-, (E)- (9CI) 
• 138387-16-3 CIS,TRANS-DOXEPIN-D3 
• 138387-19-6 5-Oxa-2-aza-spiro[3.5]non... 
• 13838-78-3 5-Methyl-1,3-thiazole-2-carboxaldehyde 
• 138391-16-9 P protein, parainfluenza virus 1 
• 138391-18-1 pal-1 protein 
• 13839-12-8 3-Buten-2-one, 4-amino-3-bromo- 

Recommend Products

• 90-46-0  9-hydroxyxanthene 
• 66294-51-7  4,4'-sulfonylbis(1-ethylbenzene) 
• 100-41-4  ethylbenzene 
• 1565-17-9  4-acetylbenzenesulfonamide 
• 965-82-2  DK₃₇ 
• 3173-53-3  Cyclohexyl isocyanate 
• 102607-92-1  N-([(4-chlorophenyl)amino]carbonyl)-4-ethylbenzenesulfonamide 
• 104-12-1  p-chlorphenylisocyanate 
• 762-42-5  dimethyl acetylenedicarboxylate 
• 603-35-0  triphenylphosphine 
• 219762-39-7  3-(2-chloro-4-phenylbenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylic acid 
• 1336-21-6  ammonium hydroxide 
• 16712-69-9  p-ethylbenzenesulfonyl chloride 
• 1469876-05-8  9-((4-ethylphenyl)sulfonyl)-9H-carbazole