1H,3H-2,1,3-Benzothiadiazole 2,2-dioxide

Base Information

• Chemical Name: 1H,3H-2,1,3-Benzothiadiazole 2,2-dioxide
• CAS No.: 1615-06-1
• Molecular Formula: C6H6N2O2S
• Molecular Weight: 170.192
• Hs Code.: 2902909090
• European Community (EC) Number: 822-549-2
• DSSTox Substance ID: DTXSID10167158
• Nikkaji Number: J102.349G
• Wikidata: Q83036475
• ChEMBL ID: CHEMBL25646
• Mol file: 1615-06-1.mol

Synonyms:1,3-BTDZD;1H,3H-2,1,3-benzothiadiazole 2,2-dioxide

Chemical Property of 1H,3H-2,1,3-Benzothiadiazole 2,2-dioxide

Chemical Property:

• Vapor Pressure: 6.11E-05mmHg at 25°C
• Melting Point: 181-183 °C
• Refractive Index: 1.613
• Boiling Point: 345.5 °C at 760 mmHg
• PKA: 5.62±0.20(Predicted)
• Flash Point: 162.8 °C
• PSA: 66.58000
• Density: 1.452 g/cm³
• LogP: 2.12560
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 0
• Exact Mass: 170.01499861
• Heavy Atom Count: 11
• Complexity: 224

Purity/Quality:

99% ^*data from raw suppliers

1,3-DIHYDRO-2,1,3-BENZOTHIADIAZOLE 2,2-DIOXIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)NS(=O)(=O)N2
• General Description: 1,3-Dihydro-2,1,3-benzothiadiazole 2,2-dioxide, also known as benzosulfamide, is a heterocyclic compound that has been identified as a potential inhibitor of the STAT3-SH2 domain, demonstrating significant activity with an IC₅₀ of 15.8 ± 0.6 μM. It interacts not only with the SH2 domain but also with nearby cysteine residues, suggesting a unique mechanism of action. Additionally, its derivatives undergo acid-catalyzed hydrolysis via a switchable A2 to A1 mechanism depending on acid concentration, highlighting its reactivity under varying conditions.

Technology Process of 1H,3H-2,1,3-Benzothiadiazole 2,2-dioxide

There total 5 articles about 1H,3H-2,1,3-Benzothiadiazole 2,2-dioxide 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: 94.0%

1,3-dibenzyl-1H,3H-2,1,3-benzothiadiazole 2,2-dioxide (1615-08-3) → 1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide (1615-06-1)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 50 ℃; for 5h; under 2660 Torr;

DOI:10.1021/jm00143a008

Reference yield: 88.0%

1,2-diamino-benzene (95-54-5) → 1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide (1615-06-1)

Guidance literature:

With SULFAMIDE; In diethylene glycol dimethyl ether; at 160 ℃;

DOI:10.3390/molecules25153509

Reference yield:

N1,N2-dibenzylbenzene-1,2-diamine (21443-66-3) → 1,3-dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide (1615-06-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 76 percent / triethylamine, SOCl₂ / tetrahydrofuran / 20 h / Ambient temperature

2: 66 percent / 3-chloroperbenzoic acid (m-CPBA) / CH₂Cl₂ / 96 h / Ambient temperature

3: 94 percent / H₂ / 5percent Pd/C / ethanol / 5 h / 50 °C / 2660 Torr

With thionyl chloride; hydrogen; triethylamine; 3-chloro-benzenecarboperoxoic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1021/jm00143a008

upstream raw materials:

1,2-diamino-benzene

1,3-dibenzyl-1H,3H-2,1,3-benzothiadiazole 2,2-dioxide

N¹,N²-dibenzylbenzene-1,2-diamine

1,3-dibenzyl-1H,3H-2,1,3-benzothiadiazole 2-oxide

Downstream raw materials:

1,3-dimethyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide

1,2-diamino-benzene