16979-15-0

Basic information

• Product Name: 1,4-Benzoxathiin 4,4-dioxide
• Synonyms: 1,4-Benzoxathiin 4,4-dioxide
• CAS NO: 16979-15-0
• Molecular Formula: C₈H₆O₃S
• Molecular Weight: 182.2
• Mol File: 16979-15-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 220.8°C at 760 mmHg
• Flash Point: 87.3°C
• Appearance: /
• Density: 1.432g/cm³
• Vapor Pressure: 0.164mmHg at 25°C
• Refractive Index: 1.615
• CAS DataBase Reference: 1,4-Benzoxathiin 4,4-dioxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,4-Benzoxathiin 4,4-dioxide(16979-15-0)
• EPA Substance Registry System: 1,4-Benzoxathiin 4,4-dioxide(16979-15-0)

Safety Data

• Hazardous Substances Data: 16979-15-0(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic compound

Structure

Tricyclic structure containing a benzene ring fused to both a thiophene and an oxygen-containing heterocycle

Common uses

Building block in the synthesis of various pharmaceuticals and agrochemicals

Potential applications

a. Corrosion inhibitor
b. Photochromic material (changes color when exposed to light)
c. Organic electronics
d. Antioxidant in polymer materials

InChI:InChI=1/C8H6O3S/c9-12(10)6-5-7-3-1-2-4-8(7)11-12/h1-6H

Upstream product

• 90-02-8 salicylaldehyde 
• 49670-40-8 2-methanesulfonyloxybenzaldehyde 

Downstream Products

• 1380035-70-0 C₁₄H₁₂O₃S 

Relevant articles and documents

Deciphering the Mechanism of Human Carbonic Anhydrases Inhibition with Sulfocoumarins: Computational and Experimental Studies

The reaction mechanism of the carbonic anhydrase-mediated hydrolysis of sulfocoumarins to sulfonic acids has been investigated on an enzyme cluster model using the B3LYP hybrid density functional theory (DFT) and the QST procedure for the Transition State (TS) search. A multistep process was highlighted, with the rate-determining step identified in the initial dual nucleophilic/acidic attack of the zinc-bound hydroxide ion to the sulfocoumarin sulfur atom and to the C3=C4 double bond. The reported multi-step process, combined to SAR analysis on a new set of derivatives, highlighted unprecedented mechanistic aspects of the CA-mediated prodrug activation, which in turn possess relevant consequences to the isoforms-selective inhibition profiles reported by such a class of compounds.

Facile synthesis of coumarin bioisosteres - 1,2-benzoxathiine 2,2-dioxides

A simple and reproducible procedure for the synthesis of bioisosteres of coumarin - 1,2-benzoxathiine 2,2-dioxide is presented. The developed method is based on the intramolecular aldol cyclization of derivatives of mesylsalicyl aldehydes in the presence