1593-60-8

Basic information

• Product Name: N-Hydroxy-4-methylbenzenesulfonamide
• Synonyms: N-Hydroxy-4-methylbenzenesulfonamide;N-(p-Tolylsulfonyl)hydroxylamine;N-Hydroxy-4-toluenesulfonamide;p-Toluenesulfonylhydroxylamine
• CAS NO: 1593-60-8
• Molecular Formula: C₇H₉NO₃S
• Molecular Weight: 187.21626
• Mol File: 1593-60-8.mol
• Article Data: 11

Chemical Properties

• Melting Point: 126-128℃ (DEC.)
• Boiling Point: 355.6±35.0 °C(Predicted)
• Appearance: /
• Density: 1.363
• PKA: 6.90±0.69(Predicted)
• CAS DataBase Reference: N-Hydroxy-4-methylbenzenesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-Hydroxy-4-methylbenzenesulfonamide(1593-60-8)
• EPA Substance Registry System: N-Hydroxy-4-methylbenzenesulfonamide(1593-60-8)

Safety Data

• Hazardous Substances Data: 1593-60-8(Hazardous Substances Data)

Usage

General Description

N-Hydroxy-4-methylbenzenesulfonamide is a chemical compound that belongs to the class of sulfonamides, which are organic compounds containing a sulfonyl group attached to an amine group. This specific compound consists of a hydroxyl group attached to a methyl-substituted benzene ring, with a sulfonamide functional group. It is typically used as an intermediate in the synthesis of pharmaceuticals and agrochemicals, and as a rubber vulcanization accelerator. N-Hydroxy-4-methylbenzenesulfonamide has the potential for use in a variety of industrial applications due to its unique chemical properties. It is important to handle this chemical with care and follow safety guidelines when working with it.

Synthetic route

p-toluenesulfonyl chloride (98-59-9) → p-toluenesulfonylhydroxylamine (1593-60-8)

Conditions	Yield
With hydroxylamine hydrochloride; magnesium oxide In tetrahydrofuran; methanol; water at 20℃;	87.5%
With hydroxylamine hydrochloride; magnesium oxide In methanol; water at 20℃; for 2h; chemoselective reaction;	85%
With hydroxylamine hydrochloride; magnesium oxide In tetrahydrofuran; methanol; water at 25℃; for 2h; Inert atmosphere; Schlenk technique;	85%

C26H23NO3S → p-toluenesulfonylhydroxylamine (1593-60-8)

Conditions	Yield
With boron trifluoride diethyl etherate In methanol; dichloromethane at 20℃; for 4h;	80%

toluene-4-sulfonamide (70-55-3) → p-toluenesulfonylhydroxylamine (1593-60-8)

Conditions	Yield
With water; potassium carbonate; p-toluenesulfonyl chloride In tetrahydrofuran; methanol at 0 - 20℃; for 3h;	42%

p-Toluolsulfonylnitrit (66021-66-7) → p-toluenesulfonylhydroxylamine (1593-60-8)

Conditions	Yield
With sodium tetrahydroborate In 1,4-dioxane at 5 - 10℃; for 0.666667h;	16%

p-toluenesulfonyl chloride (98-59-9) + (+-)-(3ar,6ac)-octahydro-pentalene-1ξ,4ξ-diol → p-toluenesulfonylhydroxylamine (1593-60-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 89 percent / pyridine / CH2Cl2 / 3 h / 20 °C 2: 80 percent / BF3*OEt2 / CH2Cl2; methanol / 4 h / 20 °C View Scheme

p-toluene sulfinic acid (536-57-2) + alkali → p-toluenesulfonylhydroxylamine (1593-60-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 54 percent / N2O4 / CCl4; diethyl ether / 0.17 h / 0 °C 2: 16 percent / NaBH4 / dioxane / 0.67 h / 5 - 10 °C View Scheme

6-fluoro-1H-indole (399-51-9) + p-toluenesulfonylhydroxylamine (1593-60-8) → 6-fluoro-3-[(4-methylphenyl)thio]indole (1622221-69-5)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	99%

p-toluenesulfonylhydroxylamine (1593-60-8) + 1,1,1,3,3,3-hexamethyl-disilazane (999-97-3) → C10H17NO3SSi (81974-63-2)

Conditions	Yield
With <(C6H5O)PO>2NH In dichloromethane for 0.833333h; Heating;	98.5%

3,4-dihydro-2H-pyran (110-87-2) + p-toluenesulfonylhydroxylamine (1593-60-8) → O-(Tetrahydro-2H-pyran-2-yl)-N-tosylhydroxylamine (135733-20-9)

Conditions	Yield
In dichloromethane for 0.5h;	98%

indole (120-72-9) + p-toluenesulfonylhydroxylamine (1593-60-8) → 3-[(4-methylphenyl)sulfanyl]-1H-indole (32884-74-5)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Catalytic behavior; Solvent; Reagent/catalyst; Inert atmosphere; Sealed tube; regioselective reaction;	98%

5-chloro-1H-indole (17422-32-1) + p-toluenesulfonylhydroxylamine (1593-60-8) → 5-chloro-3-[(4-methylphenyl)sulfanyl]-1H-indole (1622221-68-4)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	98%

4-bromo-1H-indole (52488-36-5) + p-toluenesulfonylhydroxylamine (1593-60-8) → 4-bromo-3-(p-tolylthio)-1H-indole

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

5-methoxylindole (1006-94-6) + p-toluenesulfonylhydroxylamine (1593-60-8) → 5-methoxy-3-[(4-methylphenyl)sulfanyl]-1H-indole

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	97%

5-bromo-1H-indole (10075-50-0) + p-toluenesulfonylhydroxylamine (1593-60-8) → 5-bromo-3-[(4-methylphenyl)thio]-1H-indole

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	96%

p-toluenesulfonylhydroxylamine (1593-60-8) + 1,1-bis(p-chlorophenyl)-3-phenylpropargyl alcohol (408526-05-6) → 5,5-Bis(4-chlorophenyl)-3-phenyl-2-tosyl-2,5-dihydroisoxazole (1415035-03-8)

Conditions	Yield
With ytterbium(III) triflate In dichloromethane for 6h; Reflux;	95%

1-methylindole (603-76-9) + p-toluenesulfonylhydroxylamine (1593-60-8) → 1-methyl-3-[(4-methylphenyl)sulfanyl]-1H-indole (1415328-91-4)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	95%

6-chloroindole (17422-33-2) + p-toluenesulfonylhydroxylamine (1593-60-8) → 6-chloro-3-[(4-methylphenyl)thio]indole (1622221-70-8)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	95%

p-toluenesulfonylhydroxylamine (1593-60-8) + 5-nitroindole (6146-52-7) → 5-nitro-3-[(4-methylphenyl)sulfanyl]-1H-indole (1331782-22-9)

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; iodine In butan-1-ol at 120℃; for 15h; Inert atmosphere; Sealed tube; regioselective reaction;	93%

p-toluenesulfonylhydroxylamine (1593-60-8) + 4-methoxyphenylacetylen (768-60-5) → (E)-1-((2-iodo-2-(4-methoxyphenyl)vinyl)sulfonyl)-4-methylbenzene (110210-17-8)

Conditions	Yield
With iodine; potassium carbonate In ethanol at 60℃; for 6h; Green chemistry;	90%

p-toluenesulfonylhydroxylamine (1593-60-8) + tert-butyldimethylsilyl chloride (18162-48-6) → N-(tert-butyldimethylsilyloxy)-4-methylbenzenesulfonamide (1028432-04-3)

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;	89%

3-methoxybenzenethiol (15570-12-4) + p-toluenesulfonylhydroxylamine (1593-60-8) → di(4-methyl)phenylthiosulfonate (2943-42-2) + S-(3-methoxyphenyl) 4-methylbenzenesulfonothioate

Conditions	Yield
With iodine; potassium carbonate In ethanol at 60℃; for 6h; Mechanism; Temperature; Solvent; Reagent/catalyst; Green chemistry; regioselective reaction;	A 8% B 89%

p-toluenesulfonylhydroxylamine (1593-60-8) + para-thiocresol (106-45-6) → di(4-methyl)phenylthiosulfonate (2943-42-2)

Conditions	Yield
With iodine; potassium carbonate In ethanol at 60℃; for 6h; Green chemistry;	89%

4-Methoxystyrene (637-69-4) + p-toluenesulfonylhydroxylamine (1593-60-8) → 1-(4-methoxyphenyl)-2-tosylethan-1-one oxime (1377813-95-0)

Conditions	Yield
With tetrabutylammonium periodite In dichloromethane at -20 - 40℃; for 3h; Inert atmosphere;	88%

1,3-diphenyl-1-propyn-3-ol (1817-49-8) + p-toluenesulfonylhydroxylamine (1593-60-8) → N-(1,3-diphenylprop-2-yn-1-yl)-N-hydroxy-4-methylbenzenesulfonamide (1415035-26-5)

Conditions	Yield
With toluene-4-sulfonic acid In dichloromethane at 20℃; for 0.333333h; Inert atmosphere;	88%
With iodine In dichloromethane; water at 25℃; for 3h;	38%

1-(4-chlorophenyl)-1,3-diphenylprop-2-yn-1-ol (62698-34-4) + p-toluenesulfonylhydroxylamine (1593-60-8) → 5-(4-chlorophenyl)-3,5-diphenyl-2-tosyl-2,5-dihydroisoxazole (1415035-02-7)

Conditions	Yield
With ytterbium(III) triflate In dichloromethane for 3h; Reflux;	86%

1,1-diphenyl-3-p-fluorophenylpropargyl alcohol (1192167-43-3) + p-toluenesulfonylhydroxylamine (1593-60-8) → 3-(4-fluorophenyl)-5,5-diphenyl-2-tosyl-2,5-dihydroisoxazole (1415035-06-1)

Conditions	Yield
With ytterbium(III) triflate In dichloromethane at 25℃; for 6h;	86%

1-bromo-4-ethenyl-benzene (2039-82-9) + p-toluenesulfonylhydroxylamine (1593-60-8) → 1-(4-bromophenyl)-2-tosylethan-1-one oxime (1377813-89-2)

Conditions	Yield
With tetrabutylammonium periodite In dichloromethane at -20 - 40℃; for 3h; Inert atmosphere;	85%

1-trifluoromethyl-4-vinyl-benzene (402-50-6) + p-toluenesulfonylhydroxylamine (1593-60-8) → 2-(toluene-4-sulfonyl)-1-(4-trifluoromethylphenyl)ethanone oxime (1377813-92-7)

Conditions	Yield
With tetrabutylammonium periodite In dichloromethane at -20 - 40℃; for 3h; Inert atmosphere;	85%

2-fluorostyrene (394-46-7) + p-toluenesulfonylhydroxylamine (1593-60-8) → 1-(2-fluorophenyl)-2-tosylethanone oxime (1377813-91-6)

Conditions	Yield
With tetrabutylammonium periodite In dichloromethane at -20 - 40℃; for 3h; Inert atmosphere;	85%

Upstream product

• 66021-66-7 p-TolSO₂NO 
• 70-55-3 toluene-4-sulfonamide 
• 536-57-2 p-toluene sulfinic acid 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 24230-23-7 N-(4-Nitro-benzolsulfonyloxy)-toluol-4-sulfonamid 
• 81974-63-2 C₁₀H₁₇NO₃SSi 
• 10409-07-1 bis(4-methylphenyl)disulfone 
• 711-28-4 N-methoxy-N-methyl-toluene-4-sulfonamide 
• 71535-50-7 N-tosyl-2-benzylaziridine 
• 336784-74-8 2-cyclohexyl-1-tosylaziridine 
• 773887-29-9 N-tosyl-2-nonylaziridine 
• 148961-16-4 2-hexyl-1-(toluene-4-sulfonyl)-aziridine 
• 421547-49-1 1-(4-methylbenzenesulfonyl)-2-pentylaziridine 
• 116905-61-4 2-butyl-N-tosylaziridine 
• 147054-74-8 N-(p-toluenesulfonyl)-2,3-diphenylaziridine 
• 1313223-38-9 2-(2-methoxyphenyl)-1-tosylaziridine 
• 97401-87-1 N-tosyl-2-(p-tolyl)aziridine 
• 1111321-35-7 rac-N-(p-tolylsulfonyl)-2-(2-methylphenyl)aziridine 

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