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

Chemical Properties

white crystalline powder

Uses

Different sources of media describe the Uses of 1694-06-0 differently. You can refer to the following data:
1. 4-Methylphenylsulfonylurea can be used as pharmaceutical intermediate.
2. 4-Methylphenylsulfonylurea is used in the synthesis of Glyburide (G598350), a second generation sulfonylurea with hypoglycemic activity. Glyburide is an antidiabetic agent.
3. N-(p-Toluenesulfonyl)urea is used in the synthesis of Glyburide (G598350), a second generation sulfonylurea with hypoglycemic activity. Glyburide is an antidiabetic agent.

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

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

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-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.