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

Description

N-Hydroxy-4-methylbenzenesulfonamide is a chemical compound that belongs to the class of sulfonamides, characterized by the presence of a sulfonyl group attached to an amine group. This specific compound features a hydroxyl group connected to a methyl-substituted benzene ring, along with a sulfonamide functional group. It is known for its unique chemical properties and is commonly utilized as an intermediate in the synthesis of pharmaceuticals and agrochemicals, as well as a rubber vulcanization accelerator.

Uses

Used in Pharmaceutical and Agrochemical Synthesis:
N-Hydroxy-4-methylbenzenesulfonamide is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals due to its unique chemical structure and reactivity. It plays a crucial role in the development of new drugs and pesticides, contributing to advancements in healthcare and agriculture.
Used in Rubber Vulcanization:
N-Hydroxy-4-methylbenzenesulfonamide is used as a rubber vulcanization accelerator in the rubber industry. It enhances the vulcanization process, improving the strength, elasticity, and durability of rubber products. This application is vital for the production of high-quality rubber goods, such as tires, hoses, and seals.
Used in Industrial Applications:
Due to its unique chemical properties, N-Hydroxy-4-methylbenzenesulfonamide has potential applications in various industrial sectors. Its versatility allows it to be used in the development of new materials, coatings, and other chemical processes, contributing to innovation and progress in multiple industries.
It is essential to handle N-Hydroxy-4-methylbenzenesulfonamide with care and follow safety guidelines when working with this chemical compound to ensure the safety of individuals and the environment.

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

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

Downstream Products

• 1518-00-9 3-methyl-2-(toluene-4-sulfonyl)-2H-isoxazol-5-one 
• 75732-31-9 N-(p-methylbenzenesulfonyl)-N,O-bis(trimethylsilyl)hydroxylamine 
• 56410-05-0 Z-β-Ala-OY 
• 56410-03-8 Z-Gly-OY 
• 66021-66-7 p-TolSO₂NO 
• 10409-07-1 bis(4-methylphenyl)disulfone 
• 711-28-4 N-methoxy-N-methyl-toluene-4-sulfonamide 
• 70622-46-7 iron(II) nitrosyl meso-(tetraphenyl) porphyrinate 
• 1377813-85-8 1-phenyl-2-p-tosylethan-1-one oxime 
• 1377813-86-9 1-(4-chlorophenyl)-2-tosylethan-1-one oxime 
• 1377813-95-0 1-(4-methoxyphenyl)-2-tosylethan-1-one oxime 
• 1377813-99-4 1-(naphthalen-1-yl)-2-tosylethanone oxime 
• 1377813-97-2 1-(3,4-dimethoxyphenyl)-2-tosylethanone oxime 
• 1377813-98-3 C₁₆H₁₅NO₅S 

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