1615-06-1

Basic information

• Product Name: 1,3-DIHYDRO-2,1,3-BENZOTHIADIAZOLE 2,2-DIOXIDE
• Synonyms: 1,3-DIHYDRO-BENZO[1,2,5]THIADIAZOLE 2,2-DIOXIDE;1,3-DIHYDRO-2,1,3-BENZOTHIADIAZOLE 2,2-DIOXIDE;1H,3H-2,1,3-benzothiadiazole 2,2-dioxide;1,3-Dihydrobenzo[c][1,2,5]thiadiazole 2,2-dioxide
• CAS NO: 1615-06-1
• Molecular Formula: C₆H₆N₂O₂S
• Molecular Weight: 170.19
• Mol File: 1615-06-1.mol

Chemical Properties

• Melting Point: 181-183 °C
• Boiling Point: 345.5 °C at 760 mmHg
• Flash Point: 162.8 °C
• Appearance: /
• Density: 1.452 g/cm³
• Vapor Pressure: 6.11E-05mmHg at 25°C
• Refractive Index: 1.613
• PKA: 5.62±0.20(Predicted)
• CAS DataBase Reference: 1,3-DIHYDRO-2,1,3-BENZOTHIADIAZOLE 2,2-DIOXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-DIHYDRO-2,1,3-BENZOTHIADIAZOLE 2,2-DIOXIDE(1615-06-1)
• EPA Substance Registry System: 1,3-DIHYDRO-2,1,3-BENZOTHIADIAZOLE 2,2-DIOXIDE(1615-06-1)

Safety Data

• Hazardous Substances Data: 1615-06-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C6H6N2O2S/c9-11(10)7-5-3-1-2-4-6(5)8-11/h1-4,7-8H

Upstream product

• 78973-88-3 1,3-dibenzyl-1H,3H-2,1,3-benzothiadiazole 2-oxide 
• 21443-66-3 N¹,N²-dibenzylbenzene-1,2-diamine 
• 1615-08-3 1,3-dibenzyl-1H,3H-2,1,3-benzothiadiazole 2,2-dioxide 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 1615-08-3 1,3-dibenzyl-1H,3H-2,1,3-benzothiadiazole 2,2-dioxide 
• 31378-12-8 1,3-dimethyl-1,3-dihydro-2,1,3-benzothiadiazole 2,2-dioxide 
• 95-54-5 1,2-diamino-benzene 

Relevant articles and documents

Towards the inhibition of protein–protein interactions (PPIs) in STAT3: Insights into a new class of benzothiadiazole derivatives

Signal transducer and activator of transcription 3 (STAT3) is a validated anticancer target due to the relationship between its constitutive activation and malignant tumors. Through a virtual screening approach on the STAT3-SH2 domain, 5,6-dimethyl-1H,3H-2,1,3-benzothiadiazole-2,2-dioxide (1) was identified as a potential STAT3 inhibitor. Some benzothiadiazole derivatives were synthesized by employing a versatile methodology, and they were tested by an AlphaScreen-based assay. Among them, benzosulfamide 1 showed a significant activity with an IC50 = 15.8 ± 0.6 μM as a direct STAT3 inhibitor. Notably, we discovered that compound 1 was also able to interact with cysteine residues located around the SH2 domain. By applying mass spectrometry, liquid chromatography, NMR, and UV spectroscopy, an in-depth investigation was carried out, shedding light on its intriguing and unexpected mechanism of interaction.

Acid-catalyzed hydrolysis of 5-substituted-1H,3H-2,1,3-benzothiadiazole 2,2-dioxides (5-substituted benzosulfamides): Kinetic behavior and mechanistic interpretations

The acid-catalyzed hydrolysis of a series of 5-substituted-1H,3H-2,1,3-benzothiadiazole 2,2-dioxides has been investigated in aqueous solutions of sulfuric, perchloric, and hydrochloric acid at 85.0 ± 0.05 °C. Analysis of the kinetic data by the excess acidity method, Arrhenius parameters, the order of the catalytic effects of strong acids, the kinetic deuterium isotope effect, and the substituent effect have indicated that the hydrolysis of 5-substituted benzosulfamides 1a, 1b, 1c, 1d occur with a mechanistic switchover from A2 to A1 in the studied range: an A2 mechanism in low acidity regions and an A1 mechanism in high acid concentrations.

BICYCLICALLY SUBSTITUTED URACILS AND THE USE THEREOF

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Microwave-assisted synthesis of some substituted sulfamides

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