1694-06-0

Basic information

• Product Name: 4-Methylphenylsulfonylurea
• Synonyms: 4-tolylsulfonylurea;N-(Aminocarbonyl)-4-methylbenzensulfona-mide;p-Tolysulfonylurea;P-TOLUENESULFONYLUREA;P-TOLUENESULPHONYLUREA;P-TOLYLSULFONYLUREA;P-TOLYLSULFONGLUREA;4-TOLUENESULFONYLUREA
• CAS NO: 1694-06-0
• Molecular Formula: C₈H₁₀N₂O₃S
• Molecular Weight: 214.24
• EINECS: 216-900-3
• Product Categories: chemical additive;pharmaceutical intermediate
• Mol File: 1694-06-0.mol
• Article Data: 6

Chemical Properties

• Melting Point: 196-198 °C
• Appearance: white crystalline powder
• Density: 1.3844 (rough estimate)
• Refractive Index: 1.5690 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: 5.07±0.10(Predicted)
• Water Solubility: 777.9mg/L(37 oC)
• CAS DataBase Reference: 4-Methylphenylsulfonylurea(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Methylphenylsulfonylurea(1694-06-0)
• EPA Substance Registry System: 4-Methylphenylsulfonylurea(1694-06-0)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 45-36/37/39-26
• Hazardous Substances Data: 1694-06-0(Hazardous Substances Data)

Usage

Description

4-Methylphenylsulfonylurea is a white crystalline powder that serves as a crucial intermediate in the pharmaceutical industry, particularly in the synthesis of various medications.

Uses

Used in Pharmaceutical Industry:
4-Methylphenylsulfonylurea is used as a pharmaceutical intermediate for the synthesis of various drugs, including Glyburide (G598350), a second-generation sulfonylurea with hypoglycemic activity. Glyburide is an essential antidiabetic agent that helps regulate blood sugar levels in patients with diabetes.
Additionally, 4-Methylphenylsulfonylurea is also used in the synthesis of N-(p-Toluenesulfonyl)urea, which is another key component in the production of Glyburide. This highlights the importance of 4-Methylphenylsulfonylurea in the development and manufacturing of life-saving medications for the treatment of diabetes.

InChI:InChI=1/C8H10N2O3S/c1-6-2-4-7(5-3-6)14(12,13)10-8(9)11/h2-5H,1H3,(H3,9,10,11)

Upstream product

• 5465-99-6 N¹-tosyl-N²-nitroguanidine 
• 98-59-9 p-toluenesulfonyl chloride 
• 57-13-6 urea 
• 4083-64-1 Tosyl isocyanate 
• 123-77-3 Azodicarboxamid 
• 917-61-3 sodium isocyanate 
• 70-55-3 toluene-4-sulfonamide 
• 50881-55-5 N-Chlorsulfonyl-N'-(p-tolylsulfonyl)-harnstoff 
• 590-28-3 potassium cyanate 
• 98953-53-8 N-p-Toluolsulfonyl-N'-formyl-harnstoff 

Downstream Products

• 93021-02-4 1-(5-phenyl-[1,2,4]thiadiazol-3-yl)-3-(toluene-4-sulfonyl)-urea 
• 2619-16-1 N,N-bis[(2-cyanoethyl)]-4-methylbenzenesulfonamide 

Relevant articles and documents

Synthesis method of P-toluenesulfonyl semicarbazide foaming agent

The invention discloses a synthesis method of a p-toluenesulfonyl semicarbazide foaming agent. The synthesis method comprises the following steps: S1, reducing p-toluenesulfonyl chloride into a p-toluenesulfinate in the presence of an inorganic alkali by using p-toluenesulfonyl chloride as an initial raw material, sodium sulfite as a reducing agent and water as a solvent to obtain a p-toluenesulfinate aqueous solution; and S2, adding azodicarbonamide into the p-toluenesulfinate aqueous solution obtained in the step S1 for a reaction, stopping the reaction when no gas is released, and carryingout cooling, filtering, water washing and drying to obtain a target product, namely the p-toluenesulfonyl semicarbazide, wherein the reaction temperature in the step S2 is 70-90 DEG C, preferably, thereaction temperature in the step S2 is 78-82 DEG C. The synthesis method disclosed by the invention is safe and environmentally friendly, is high in yield, and is simple to operate; the raw materialsare convenient and easy to obtain and are low in cost; and thus the synthesis method is a synthesis route suitable for industrial production.

Preparation method for high-purity gliclazide intermediate namely p-toluenesulfonylurea

The invention discloses a simple and convenient preparation method for p-toluenesulfonylurea. The preparation method comprises the following reaction steps: according to a reaction flow as shown in aformula 3 which is described in the specification, filling a reaction container with nitrogen gas to replace air in the reaction container, then adding an organic solvent and p-toluenesulfonyl isocyanate, then charging ammonia gas, carrying out a reaction at a low temperature under stirring so as to generate a crude p-toluenesulfonylurea product, then carrying out filtering, adding acetonitrile/water for refluxing, carrying out programmed cooling (10 DEG C/h), and carrying out centrifuging and drying so as to obtain a white crystal, namely, the p-toluenesulfonylurea. The preparation method provided by the invention prepares the p-toluenesulfonylurea by ammonolysis of the p-toluenesulfonyl isocyanate with the ammonia gas in toluene and can reach a yield up to 96.3%; and a product has a purity of 99.9% or more, is a white crystalline solid and is free of impurities. The preparation method provided by the invention has the following advantages: operation is simple and convenient; conditions are mild; post-treatment is easy; and a product has high purity and high yield, is a white crystal and facilitates storage.

SYNTHESIS AND PROPERTIES OF ISOMERIC N-ARYLSULFONYL-N-NITROGUANIDINES

Methods were developed for the synthesis of isomeric N-tosyl-N-nitroguanidines with the nitro group at various nitrogen atoms.Their reactions with diazomethane, acetylacetone, and primary amines and their alkaline hydrolysis were studied.A new method is developed for the production of N1-tosyl-N2-alkylguanidines.