567-19-1

Basic information

• Product Name: 7-chloro-9$l^{6}-thia-8-azabicyclo[4.3.0]nona-1,3,5,7-tetraene 9,9-dio xide
• Synonyms: 3-CHLORO-PSI-SACCHARIN;3-chloro-1，2.benziso thiazole-1，1-dioxide;3-chloro-1,2-benzothiazole 1,1-dioxide;3-Chloro-1,2-benzothiazole-1,1-dione;7-chloro-9$l^{6}-thia-8-azabicyclo[4.3.0]nona-1,3,5,7-tetraene 9,9-dio xide
• CAS NO: 567-19-1
• Molecular Formula: C₇H₄ClNO₂S
• Molecular Weight: 201.633
• Mol File: 567-19-1.mol
• Article Data: 63

Chemical Properties

• Melting Point: 145-147 °C
• Boiling Point: 377.1 °C at 760 mmHg
• Flash Point: 181.9 °C
• Appearance: colorless solid
• Density: 1.64 g/cm³
• Vapor Pressure: 1.5E-05mmHg at 25°C
• Refractive Index: 1.695
• PKA: -7.40±0.20(Predicted)
• CAS DataBase Reference: 7-chloro-9$l^{6}-thia-8-azabicyclo[4.3.0]nona-1,3,5,7-tetraene 9,9-dio xide(CAS DataBase Reference)
• NIST Chemistry Reference: 7-chloro-9$l^{6}-thia-8-azabicyclo[4.3.0]nona-1,3,5,7-tetraene 9,9-dio xide(567-19-1)
• EPA Substance Registry System: 7-chloro-9$l^{6}-thia-8-azabicyclo[4.3.0]nona-1,3,5,7-tetraene 9,9-dio xide(567-19-1)

Safety Data

• Hazardous Substances Data: 567-19-1(Hazardous Substances Data)

Usage

General Description

The chemical 7-chloro-9$l^{6}-thia-8-azabicyclo[4.3.0]nona-1,3,5,7-tetraene 9,9-dioxide, which belongs to the class of organic compounds known as organochlorides, is a complex chemical compound. 7-chloro-9$l^{6}-thia-8-azabicyclo[4.3.0]nona-1,3,5,7-tetraene 9,9-dio xide incorporates a chloro moiety along with a bicyclo structure, suggesting it might exhibit distinct reactivity and properties. The molecules in this class contain one or more atoms of chlorine. Also, being an organic compound, it consists mainly of carbon atoms along with hydrogen and other atoms. However, detailed information about the physical properties, uses or potential health effects of this specific chemical isn't readily available, indicating that it may not be widely used or studied.

InChI:InChI=1/C7H4ClNO2S/c8-7-5-3-1-2-4-6(5)12(10,11)9-7/h1-4H

Upstream product

• 10026-13-8 phosphorus pentachloride 
• 81-07-2 saccharin 
• 7719-09-7 thionyl chloride 
• 57683-71-3 methyl 2-(aminosulfonyl)benzoate 
• 119300-80-0 2-methoxycarbonyl-benzenesulfinic acid 
• 134-20-3 2-carbomethoxyaniline 
• 5669-05-6 1,2-benzoisothiazole 1,1-dioxide 

Downstream Products

• 102362-98-1 3,3-dimethyl-2,3-dihydro-1,2-benzoisothiazole 1,1-dioxide 
• 108950-06-7 AG-205/36484052 
• 53983-81-6 2,3-Dihydro-3,3-diphenyl-1,2-benzisothiazole 1,1-dioxide 
• 106882-99-9 N'-(1,1-dioxo-1λ⁶-benz[d]isothiazol-3-yl)-N,N-dimethyl-p-phenylenediamine 
• 101187-51-3 N-(1,1-dioxo-1λ⁶-benz[d]isothiazol-3-yl)-anthranilic acid methyl ester 
• 108013-61-2 (2,4-dimethyl-phenyl)-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yl)-amine 
• 7677-47-6 3-Methyl-amino-1,2-benzisothiazol-1,1-dioxid 
• 68287-31-0 [2-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-ylamino)-phenyl]-methanol 
• 27148-09-0 3-Propyl-amino-1,2-benzisothiazol-1,1-dioxid 
• 68229-69-6 3-pentachlorophenylsulfanyl-benzo[d]isothiazole 1,1-dioxide 
• 68229-62-9 3-pentachlorophenoxy-benzo[d]isothiazole 1,1-dioxide 
• 13618-13-8 cyclohexanone O-(1,1-dioxo-1H-1λ⁶-benzo[d]isothiazol-3-yl)-oxime 
• 38949-27-8 3-pentabromophenoxy-benzo[d]isothiazole 1,1-dioxide 
• 18715-95-2 3-[(1'R)-menthoxy]-1,2-benzisothiazole 1,1-dioxide 

Relevant articles and documents

The thermal sigmatropic isomerization of pseudosaccharyl crotyl ether

The thermally induced sigmatropic isomerization of the pseudosaccharyl crotyl ether, 3-(E)-but-2- enoxy)-1,2-benzisothiazole 1,1-dioxide (CBID), has been investigated by using temperature dependent infrared spectroscopy, differential scanning calorimetry (DSC), and polarized light thermomicroscopy. The reaction can take place in both melted and crystalline phases, affording the product resulting from the [3,3′] migration of the allylic system from O to N, 2-(E)-1-methylprop-2-en-1,2-benzisothiazol-3(2H)- one 1,1-dioxide (CBIOD). In the melt, the activation energy of the process was determined as being 49.1±5.3 kJ mol-1, with k=(22.2±0.6)×10 4 s-1 at 140 °C. In the solid state, at 110 °C, the rate constant drops by one order of magnitude [k=(1.46±0.07) ×104 s-1]. The enthalpy of reaction, determined by DSC, isΔrxH=-27.0±0.8 kJ mol-1. Assignments were proposed for the infrared spectra of the observed neat condensed phases of the two compounds.

Structure and photochemistry of a saccharyl thiotetrazole

The molecular structure and photochemistry of 5-thiosaccharyl-1-methyltetrazole (TSMT) were studied by means of matrix-isolation FTIR spectroscopy, X-ray crystallography, and theoretical calculations. The calculations predicted two conformers of TSMT that differ in energy by more than 15 kJ mol-1. The infrared spectrum of TSMT isolated in solid argon was fully assigned on the basis of the spectrum calculated (O3LYP/6-311++G(3df,3pd)) for the most stable conformer. In the crystal, TSMT molecules were found to assume the same conformation as for the isolated molecule, with each molecule forming four hydrogen bonds with three neighboring molecules, leading to a network of TSMT oligomers. Upon UV (λ = 265 nm) irradiation of the matrix-isolated TSMT, two photodegradation pathways were observed, both arising from cleavage of the tetrazolyl ring. Pathway a involves cleavage of the N1-N2 and N3-N4 bonds with extrusion of N2, leading to photostable diazirine and thiocarbodiimide derivatives. The photostability of the photoproduced diazirine under the conditions used precluded its rearrangement to the nitrile imine, as reported for 5-phenyltetrazole by Bégué et al. (J. Am. Chem. Soc. 2012, 134, 5339). Pathway b involves cleavage of the C5-N1 and N4-N3 bonds, leading to a thiocyanate and methyl azide, the latter undergoing subsequent fragmentation to give CNH.

Synthesis, characterization and antimicrobial evaluation of new 3-(Alkyl/Arylamino)benzo[d]isothiazole 1,1-derivatives

The saccharine nucleus has long been recognized as a significant component in medicine. A series of pseudo-saccharine amines derivatives (7a-j) were synthesized and examined for their antibacterial activity. After testing all compounds, 7b, 7f, 7g, 7i and 7j were found most effective against Escherichia coli, Streptococcus aureus and Bacillus subtilis strains. The MIC of the compound was found from 4.6 to 16.1 μM. Further, compound 7f and 7i exhibited excellent activity against E.coli and Bacillus subtilis with MIC value 4.6 and 4.7 μM respectively. The compound 7b and 7i was found active against all the three bacteria. The zone inhibition was observed at 10 μM against Escherichia coli, Staphylococcus aureus and Bacillus subtilis at 0.9, 1.8, 3.9 respectively for 7b and 1.0, 1.8 and 2.0 cm respectively for 7i.

Insight into the binding mode of HIF-2 agonists through molecular dynamic simulations and biological validation

Hypoxia-inducible factor-2 (HIF-2), a heterodimeric transcriptional protein consisting of HIF-2α and aryl hydrocarbon receptor nuclear translocator (ARNT) subunits, has a broad transcriptional profile that plays a vital role in human oxygen metabolism. M1001, a HIF-2 agonist identified by high-throughput screening (HTS), is capable of altering the conformation of Tyr281 of the HIF-2α PAS-B domain and enhancing the affinity of HIF-2α and ARNT for transcriptional activation. M1002, an analog of M1001, shows improved efficacy than M1001. However, the cocrystal structure of M1001 and HIF-2 has some defects in revealing the agonist binding mode due to the relatively low resolution, while the binding mode of M1002 remained unexplored. To in-depth understand agonist binding profiles, herein, the molecular dynamic (MD) simulations was applied to construct a stable agonist-protein model, and a possible binding mode was proposed through the analysis of the binding free energy and hydrogen bonding of the simulation results. Nine compounds were then synthesized and evaluated to verify the proposed binding mode. Among them, compound 10 manifested improved agonistic activity and reduced toxicity compared to M1002. This study provides deep insight into the binding mode of such HIF-2 agonists, which would be useful for designing novel agonists for HIF-2.