6-Aminosaccharin

Base Information

• Chemical Name: 6-Aminosaccharin
• CAS No.: 22094-62-8
• Molecular Formula: C7H6 N2 O3 S
• Molecular Weight: 198.202
• European Community (EC) Number: 853-564-2
• UNII: 8X8M8255WF
• DSSTox Substance ID: DTXSID30176601
• Nikkaji Number: J658.889A
• Wikidata: Q27465554
• Pharos Ligand ID: D852GFBGAU7Y
• ChEMBL ID: CHEMBL2016952
• Mol file: 22094-62-8.mol

Synonyms:6-aminosaccharin

Chemical Property of 6-Aminosaccharin

Chemical Property:

• Melting Point: 278 °C
• Boiling Point: °Cat760mmHg
• PKA: 1.92±0.30(Predicted)
• Flash Point: °C
• PSA: 101.13000
• Density: 1.652g/cm³
• LogP: 1.37330
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 198.00991323
• Heavy Atom Count: 13
• Complexity: 332

Purity/Quality:

99%, ^*data from raw suppliers

6-Amino-1,1-dioxo-1,2-benzothiazol-3-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=C(C=C1N)S(=O)(=O)NC2=O

Technology Process of 6-Aminosaccharin

There total 6 articles about 6-Aminosaccharin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

6-nitrosaccharin (22952-24-5) → 6-amino-1,2-benzisothiazole-3(2H)-one 1,1-dioxide (22094-62-8)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 ℃; for 4h; under 760.051 Torr;

DOI:10.1016/j.bmc.2014.01.045

Reference yield:

4-nitrotoluene-2-sulfonamide (6269-91-6) → 6-amino-1,2-benzisothiazole-3(2H)-one 1,1-dioxide (22094-62-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 56 percent / CrO₃, conc. H₂SO₄ / H₂O / 24 h / Ambient temperature

2: 63 percent / cyclohexene / 5percent Pd/C / ethanol / 2 h / Heating

With chromium(VI) oxide; sulfuric acid; cyclohexene; palladium on activated charcoal; In ethanol; water;

DOI:10.1246/bcsj.55.3824

Reference yield:

2-methyl-5-nitrobenzene-1-sulfonyl chloride (121-02-8) → 6-amino-1,2-benzisothiazole-3(2H)-one 1,1-dioxide (22094-62-8)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. aq. NH₃ / diethyl ether / 2 h / Heating

2: 56 percent / CrO₃, conc. H₂SO₄ / H₂O / 24 h / Ambient temperature

3: 63 percent / cyclohexene / 5percent Pd/C / ethanol / 2 h / Heating

With chromium(VI) oxide; ammonium hydroxide; sulfuric acid; cyclohexene; palladium on activated charcoal; In diethyl ether; ethanol; water;

DOI:10.1246/bcsj.55.3824

upstream raw materials:

6-nitrosaccharin

1-methyl-4-nitrobenzene

4-nitrotoluene-2-sulfonamide

2-methyl-5-nitrobenzene-1-sulfonyl chloride

Downstream raw materials:

6-<4-(2-bromoethyl)benzenesulfonamido>saccharin

6-(4-[3′-methylphenyl]-1H-1,2,3-triazol-1-yl)-1,2-benzisothiazole-3(2H)-one 1,1-dioxide

6-(4-phenyl-1H-1,2,3-triazol-1-yl)-1,2-benzisothiazole-3(2H)-one 1,1-dioxide

6-(N₃-(3-methoxyphenyl)ureido)saccharin

Refernces

• 1、 Han, Leiqiang,Wang, Lei,Hou, Xuben,Fu, Huansheng,Song, Weiguo,Tang, Weiping,Fang, Hao. "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". . p. 1529 - 1538. Retrieved 2014/03/21.
• 2、 Gener, Nahit,Demir, Dudu,Sonmez, Fatih,Kucukislamoglu, Mustafa. "New saccharin derivatives as tyrosinase inhibitors". experimental part. p. 2811 - 2821. Retrieved 2012/06/29.