22094-62-8

Basic information

• Product Name: 6-aminosaccharin
• Synonyms: 6-aminosaccharin;6-AMINO-1,1-DIOXO-1,2-BENZOTHIAZOL-3-ONE
• CAS NO: 22094-62-8
• Molecular Formula: C₇H₆N₂O₃S
• Molecular Weight: 198.19914
• Mol File: 22094-62-8.mol
• Article Data: 7

Chemical Properties

• Melting Point: 278 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.652g/cm³
• Refractive Index: 1.684
• PKA: 1.92±0.30(Predicted)
• CAS DataBase Reference: 6-aminosaccharin(CAS DataBase Reference)
• NIST Chemistry Reference: 6-aminosaccharin(22094-62-8)
• EPA Substance Registry System: 6-aminosaccharin(22094-62-8)

Safety Data

• Hazardous Substances Data: 22094-62-8(Hazardous Substances Data)

Usage

General Description

6-Aminosaccharin, also known as ortho-amino-benzoic acid, is an organic compound primarily utilized in the production of various dyes and pigments in the chemical industry. Its chemical formula is C7H7NO3S and its strategic structural design gives it attributes that make it versatile for applications in areas such as medicine, agriculture, and even scientific research. Despite its widespread use, however, it is considered a hazardous substance due to potential risks of skin and eye irritation, toxicity if swallowed, as well as respiratory tract irritation. Safety measures must be taken to handle and use 6-aminosaccharin appropriately.

InChI:InChI=1/C7H6N2O3S/c8-4-1-2-5-6(3-4)13(11,12)9-7(5)10/h1-3H,8H2,(H,9,10)

Upstream product

• 99-99-0 1-methyl-4-nitrobenzene 
• 121-02-8 2-methyl-5-nitrobenzene-1-sulfonyl chloride 
• 6269-91-6 4-nitrotoluene-2-sulfonamide 
• 22952-24-5 6-nitrosaccharin 

Downstream Products

• 1374832-67-3 6-(N₃-(2-fluorophenyl)ureido)saccharin 
• 1374832-81-1 6-(N₃-(3-fluorophenyl)thioureido)saccharin 
• 1374832-85-5 6-(N₃-(3-iodophenyl)thioureido)saccharin 
• 1374832-59-3 6-(N₃-(4-chlorophenyl)ureido)saccharin 
• 1374832-65-1 6-(N₃-(4-nitrophenyl)ureido)saccharin 
• 1374832-79-7 6-(N₃-(2-fluorophenyl)thioureido)saccharin 
• 1374832-49-1 6-(N₃-phenylureido)saccharin 
• 1374832-73-1 6-(N₃-phenylthioureido)saccharin 
• 1374832-55-9 6-(N₃-(4-methylphenyl)ureido)saccharin 
• 1374832-71-9 6-(N₃-(4-fluorophenyl)ureido)saccharin 
• 1374832-53-7 6-(N₃-(4-methoxyphenyl)ureido)saccharin 
• 1374832-77-5 6-(N₃-(4-methoxyphenyl)thioureido)saccharin 
• 1374832-61-7 6-(N₃-(3,4-dichlorophenyl)ureido)saccharin 
• 1374832-83-3 6-(N₃-(4-fluorophenyl)thioureido)saccharin 

Relevant articles and documents

A convenient synthesis of 2-methoxycarbonyl-5-iodobenzene sulfonamide

A convenient and concise synthesis of 2-methyl-5-nitrobenzene sulfonamide can be achieved by sulfochlorination and ammoniation with p-nitrotoluene as raw materials for an 81.2 % yield. 6-Aminosaccharin can be produced via oxidation and reduction in a 64.3

Design, synthesis and preliminary bioactivity studies of 1,2-dihydrobenzo[d]isothiazol-3-one-1,1-dioxide hydroxamic acid derivatives as novel histone deacetylase inhibitors

Histone deacetylase (HDAC) is a clinically validated target for antitumor therapy. In order to increase HDAC inhibition and efficiency, we developed a novel series of saccharin hydroxamic acids as potent HDAC inhibitors. Among them, compounds 11e, 11m, 11

New saccharin derivatives as tyrosinase inhibitors

A newly series of 6-(phenylurenyl/thiourenyl) saccharin (6a-y) derivatives were synthesized and their inhibitory effects on the diphenolase activity of banana tyrosinase were evaluated. A 70-fold purification of the enzyme with 6.85% yield was achieved by using a Sepharose 4B-l-tyrosine-p-amino benzoic acid affinity column. The result showed that all the synthesized compounds inhibited the tyrosinase enzyme activity. Among the compounds synthesized, 6-(3-iodophenylthiourenyl) saccharin (6s) was found to be most active one (Ki = 3.95 μM) and the inhibition kinetics analyzed by Lineweaver-Burk double reciprocal plots revealed that compound 6s was a competitive inhibitor. Structure-activity relationships study showed that generally, most of the 6-(phenylthiourenyl) saccharin derivatives (6m-y) exhibited higher inhibitory activity than 6-(phenylurenyl) saccharin derivatives (6a-l). An electron-withdrawing group at 3-position of phenylurenyl-ring increased in activity and the halogen series at 3-position of phenylthiourenyl-ring showed a qualitative relationship for higher inhibitory activity with increasing size and polarizability. We also calculated HOMO-LUMO energy levels and dipole moments of some selected the synthesized compounds (6a, 6h, 6m and 6s) using Gaussian software.