77375-79-2

Basic information

• Product Name: ethyl 2-(isocyanatosulfonyl)benzoate
• Synonyms: ethyl 2-(isocyanatosulfonyl)benzoate;Benzoic acid, 2-(isocyanatosulfonyl)-, ethyl ester
• CAS NO: 77375-79-2
• Molecular Formula: C10H9 N O5 S
• Molecular Weight: 255.25
• EINECS: 410-220-2
• Mol File: 77375-79-2.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 373.5±25.0 °C(Predicted)
• Appearance: /
• Density: 1.34±0.1 g/cm3(Predicted)
• CAS DataBase Reference: ethyl 2-(isocyanatosulfonyl)benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 2-(isocyanatosulfonyl)benzoate(77375-79-2)
• EPA Substance Registry System: ethyl 2-(isocyanatosulfonyl)benzoate(77375-79-2)

Safety Data

• Hazard Codes: E,Xn
• Statements: 2-14-22-41-42/43-48/22
• Safety Statements: 8-23-26-30-35-36/37/39
• Hazardous Substances Data: 77375-79-2(Hazardous Substances Data)

Usage

General Description

Ethyl 2-(isocyanatosulfonyl)benzoate is a chemical compound with the molecular formula C11H11NO5S. It is commonly used as a reagent in organic synthesis for the preparation of various functionalized compounds. The isocyanatosulfonyl group in the molecule makes it a useful building block for the synthesis of pharmaceuticals, agrochemicals, and specialty chemicals. It also has potential applications in the development of new materials and polymers. Ethyl 2-(isocyanatosulfonyl)benzoate is a highly reactive compound and should be handled with care in a controlled laboratory setting.

Upstream product

• 79-37-8 oxalyl dichloride 
• 59777-72-9 ethyl 2-(aminosulfonyl)benzoate 
• 81-07-2 saccharin 

Downstream Products

• 1416567-33-3 C₁₅H₁₅BrN₄O₆S 
• 100594-02-3 C₁₅H₁₅IN₄O₆S 

Relevant articles and documents

Sulfonylureas have antifungal activity and are potent inhibitors of Candida albicans acetohydroxyacid synthase

The sulfonylurea herbicides exert their activity by inhibiting plant acetohydroxyacid synthase (AHAS), the first enzyme in the branched-chain amino acid biosynthesis pathway. It has previously been shown that if the gene for AHAS is deleted in Candida albicans, attenuation of virulence is achieved, suggesting AHAS as an antifungal drug target. Herein, we have cloned, expressed, and purified C. albicans AHAS and shown that several sulfonylureas are inhibitors of this enzyme and possess antifungal activity. The most potent of these compounds is ethyl 2-(N-((4-iodo-6-methoxypyrimidin-2-yl)carbamoyl) sulfamoyl)benzoate (10c), which has a Ki value of 3.8 nM for C. albicans AHAS and an MIC90 of 0.7 μg/mL for this fungus in cell-based assays. For the sulfonylureas tested there was a strong correlation between inhibitory activity toward C. albicans AHAS and fungicidal activity, supporting the hypothesis that AHAS is the target for their inhibitory activity within the cell.

Intermediates for herbicidal sulfonamides

This invention relates to novel o-carbonylbenzenesulfonyl isocyanates and their use as intermediates for the preparation of sulfonylureas which are known to be active herbicides.