10543-42-7

Basic information

• Product Name: COUMARIN-6-SULFONYL CHLORIDE
• Synonyms: TIMTEC-BB SBB002796;6-CS-CL;2-OXO-2H-CHROMENE-6-SULFONYL CHLORIDE;2-OXO-2H-1-BENZOPYRAN-6-SULFONYL CHLORIDE;COUMARIN-6-SULFONYL CHLORIDE;COUMARIN-6-SULPHONYL CHLORIDE;CBI-BB ZERO/008202;2-Oxo-2H-chromene-6-sulphonyl chloride
• CAS NO: 10543-42-7
• Molecular Formula: C₉H₅ClO₄S
• Molecular Weight: 244.65
• Mol File: 10543-42-7.mol

Chemical Properties

• Melting Point: 110-113
• Boiling Point: 431.6 °C at 760 mmHg
• Flash Point: 214.8 °C
• Appearance: /
• Density: 1.591 g/cm³
• Vapor Pressure: 1.19E-07mmHg at 25°C
• Refractive Index: 1.619
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility: Slightly soluble in water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: COUMARIN-6-SULFONYL CHLORIDE(CAS DataBase Reference)
• NIST Chemistry Reference: COUMARIN-6-SULFONYL CHLORIDE(10543-42-7)
• EPA Substance Registry System: COUMARIN-6-SULFONYL CHLORIDE(10543-42-7)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 10-21
• HazardClass: 8
• Hazardous Substances Data: 10543-42-7(Hazardous Substances Data)

Usage

Uses

Used in Chemical Synthesis:
COUMARIN-6-SULFONYL CHLORIDE is used as a labeling agent for amines, amino acids, and phenols. This application is particularly useful in the identification and tracking of these molecules in various chemical and biological processes. The mild conditions required for the reaction make it a preferred choice for preserving the integrity of sensitive molecules.
Used in Derivatization:
COUMARIN-6-SULFONYL CHLORIDE is also used as a derivatizing agent for amines and phenols. This process involves the chemical modification of these molecules to enhance their properties or to facilitate their analysis. The derivatization can improve the solubility, stability, or detectability of the target molecules, making it easier to study their behavior in different environments.

InChI:InChI=1/C9H5ClO4S/c10-15(12,13)7-2-3-8-6(5-7)1-4-9(11)14-8/h1-5H

Upstream product

• 91-64-5 coumarin 
• 7790-94-5 chlorosulfonic acid 

Downstream Products

• 113789-53-0 4-(2-oxo-2H-chromene-6-sulfonylamino)-benzoic acid 
• 84015-72-5 2-oxo-2H-chromene-6-sulfonic acid anilide 
• 84015-87-2 2-Oxo-2H-chromene-6-sulfonic acid p-tolyl ester 
• 84015-88-3 2-Oxo-2H-chromene-6-sulfonic acid 4-bromo-phenyl ester 
• 84015-75-8 2-Oxo-2H-chromene-6-sulfonic acid p-tolylamide 
• 111456-29-2 coumarin-6-sulphonic acid p-formylphenyl ester 
• 84015-78-1 2-Oxo-2H-chromene-6-sulfonic acid (4-chloro-phenyl)-amide 
• 111456-28-1 coumarin-6-sulphonic acid o-formylphenyl ester 
• 84031-68-5 N-(4-methoxyphenyl)-2-oxo-2H-chromene-6-sulphonamide 
• 84015-86-1 2-Oxo-2H-chromene-6-sulfonic acid m-tolyl ester 
• 84015-85-0 2-Oxo-2H-chromene-6-sulfonic acid o-tolyl ester 
• 84015-80-5 2-Oxo-2H-chromene-6-sulfonic acid (4-nitro-phenyl)-amide 
• 84015-79-2 2-Oxo-2H-chromene-6-sulfonic acid (2-nitro-phenyl)-amide 
• 84015-77-0 2-Oxo-2H-chromene-6-sulfonic acid (2-chloro-phenyl)-amide 

Related news

Analysis of phenols in water by high-performance liquid chromatography using COUMARIN-6-SULFONYL CHLORIDE (cas 10543-42-7) as a fluorogenic precolumn label08/06/2019

A simple, sensitive and rapid reversed-phase high-performance liquid chromatography (RP-HPLC) method is proposed for the analysis of some environmentally important phenols in water. The use of coumarin-6-sulphonyl chloride (C6SCl) as a fluorescence-labeling reagent has been investigated. The com...detailed

Relevant articles and documents

Novel coumarin-6-sulfonamides as apoptotic anti-proliferative agents: synthesis, in vitro biological evaluation, and QSAR studies

Herein, we report the synthesis of different novel sets of coumarin-6-sulfonamide derivatives bearing different functionalities (4a, b, 8a–d, 11a–d, 13a, b, and 15a–c), and in vitro evaluation of their growth inhibitory activity towards the proliferation of three cancer cell lines; HepG2 (hepatocellular carcinoma), MCF-7 (breast cancer), and Caco-2 (colon cancer). HepG2 cells were the most sensitive cells to the influence of the target coumarins. Compounds 13a and 15a emerged as the most active members against HepG2 cells (IC50 = 3.48 ± 0.28 and 5.03 ± 0.39 μM, respectively). Compounds 13a and 15a were able to induce apoptosis in HepG2 cells, as assured by the upregulation of the Bax and downregulation of the Bcl-2, besides boosting caspase-3 levels. Besides, compound 13a induced a significant increase in the percentage of cells at Pre-G1 by 6.4-folds, with concurrent significant arrest in the G2-M phase by 5.4-folds compared to control. Also, 13a displayed significant increase in the percentage of annexin V-FITC positive apoptotic cells from 1.75–13.76%. Moreover, QSAR models were established to explore the structural requirements controlling the anti-proliferative activities.

Design, solvent-free synthesis and antibacterial activity evaluation of new coumarin sulfonamides

A simple cost-effective and green method was presented for the synthesis of coumarin bis sulfonamides. Seventeen novel coumarin sulfonamides were synthesized in good to high yield and purity in six steps starting from 2-amino thiazole, aniline, and 4-methoxy aniline. All of the reactions have been done under green conditions without using any hazardous solvent. The chemical structures of the products were elucidated by IR, 1H NMR, and 13C NMR spectroscopy and elemental analysis. Also, the anti-bacterial properties of the synthesized sulfonamides were investigated using two strains of Staphylococcus (gram-positive) and Escherichia coli (gram-negative) bacteria.