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

• 98-59-9 p-toluenesulfonyl chloride 
• 57-13-6 urea 
• 917-61-3 sodium isocyanate 
• 70-55-3 toluene-4-sulfonamide 
• 123-77-3 Azodicarboxamid 
• 4083-64-1 Tosyl isocyanate 
• 5465-99-6 N¹-tosyl-N²-nitroguanidine 
• 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

• 21187-98-4 gliclazide 
• 108-80-5 cyanuric acid 

Relevant articles and documents

Synthesis method of p-toluenesulfonylurea

The invention relates to a synthesis method of p-toluenesulfonylurea. The synthesis method comprises the following steps: dissolving p-toluenesulfonamide and sodium cyanate in a mixed solution of water and ethanol to react, filtering after the reaction is finished, acidifying the filtered mother solution, and filtering again, thereby finally obtaining p-toluenesulfonylurea. According to the method, no by-product or ammonia gas is generated, the yield of the target product reaches 90% or above, the purity is larger than 99%, the process is simple, operation steps are simple and convenient, theoperation environment is non-toxic and free of pollution, no waste gas is generated, production energy consumption is low, the yield is high, and the method has very high popularization value.

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.