17831-88-8

Basic information

• Product Name: 4-CHLORO-2H-CHROMEN-2-ONE
• Synonyms: AURORA KA-4413;4-CHLORO-2H-CHROMEN-2-ONE;4-chloro-2H-1-benzopyran-2-one;Einecs 241-790-9
• CAS NO: 17831-88-8
• Molecular Formula: C₉H₅ClO₂
• Molecular Weight: 180.59
• EINECS: 241-790-9
• Mol File: 17831-88-8.mol
• Article Data: 35

Chemical Properties

• Melting Point: 89-91 °C
• Boiling Point: 315.8°Cat760mmHg
• Flash Point: 168°C
• Appearance: /
• Density: 1.4g/cm³
• Vapor Pressure: 0.000428mmHg at 25°C
• Refractive Index: 1.618
• CAS DataBase Reference: 4-CHLORO-2H-CHROMEN-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-CHLORO-2H-CHROMEN-2-ONE(17831-88-8)
• EPA Substance Registry System: 4-CHLORO-2H-CHROMEN-2-ONE(17831-88-8)

Safety Data

• Hazardous Substances Data: 17831-88-8(Hazardous Substances Data)

Usage

Description

4-CHLORO-2H-CHROMEN-2-ONE, also known as 4-chlorocoumarin or 4-chloro-2-oxo-2H-chromene, is a chemical compound with a molecular formula of C9H5ClO2. It is a derivative of coumarin and belongs to the family of organic compounds known as 4-alkoxy-coumarins. 4-CHLORO-2H-CHROMEN-2-ONE is characterized by its unique chemical structure, which contributes to its diverse biological and pharmacological properties, making it a valuable intermediate in the synthesis of various functionalized coumarin derivatives.

Uses

Used in Pharmaceutical Industry:
4-CHLORO-2H-CHROMEN-2-ONE is used as a key intermediate in the synthesis of various pharmaceuticals for its potential biological activities. Its antifungal, antibacterial, and antitumor properties make it a promising candidate for the development of new drugs targeting a wide range of diseases and conditions.
Used in Agrochemical Industry:
In the agrochemical industry, 4-CHLORO-2H-CHROMEN-2-ONE is utilized as a building block in the production of agrochemicals. Its biological activities, such as antifungal and antibacterial properties, contribute to the development of effective pesticides and other agricultural chemicals to protect crops and enhance agricultural productivity.
Used in the Synthesis of Functionalized Coumarin Derivatives:
4-CHLORO-2H-CHROMEN-2-ONE serves as a valuable intermediate in the synthesis of various functionalized coumarin derivatives. Its unique chemical structure allows for the creation of compounds with diverse biological and pharmacological properties, which can be applied in different fields, including medicine, agriculture, and other industries.

InChI:InChI=1/C9H5ClO2/c10-7-5-9(11)12-8-4-2-1-3-6(7)8/h1-5H

Upstream product

• 1076-38-6 4-hydroxy[1]benzopyran-2-one 
• 541-47-9 3-Methylbutenoic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 38518-76-2 2-amino-4H-1-benzopyran-4-one 
• 127-19-5 N,N-dimethyl acetamide 
• 69-72-7 salicylic acid 
• 118-93-4 o-hydroxyacetophenone 
• 108-95-2 phenol 
• 582-24-1 1-phenyl-2-hydroxyethanone 
• 22105-09-5 4‐hydroxycoumarin 

Downstream Products

• 35817-27-7 4-ethoxy-2H-chromen-2-one 
• 91-64-5 coumarin 
• 24526-92-9 4-((2-methoxyphenyl)amino)-2H-chromen-2-one 
• 24526-94-1 4-(p-tolylamino)-2H-chromen-2-one 
• 24526-89-4 4-((4-chlorophenyl)amino)-2H-chromen-2-one 
• 4812-86-6 4-(phenylamino)-2H-chromen-2-one 
• 24526-91-8 4-((4-ethoxyphenyl)amino)-2H-chromen-2-one 
• 24526-93-0 4-(meta-tolylamino)-2H-chromen-2-one 
• 21401-60-5 N-benzyl 4-aminocoumarin 
• 145982-78-1 3-butyl-1-(o-hydroxyphenyl)hept-1-yn-3-ol 
• 145982-74-7 (Z)-5-butyl-7-(o-hydroxyphenyl)undec-6-en-5-ol 
• 73509-05-4 3-hydroxy-1-(o-hydroxyphenyl)-3-methylbutan-1-one 
• 139416-74-3 2-(3-hydroxy-3-methylbut-1-yn-1-yl)phenol 
• 145982-67-8 (E)-4-chloro-4-(o-hydroxyphenyl)-2-methylbut-3-en-2-ol 

Relevant articles and documents

Design, synthesis, and antiproliferative evaluation of novel coumarin/2-cyanoacryloyl hybrids as apoptosis inducing agents by activation of caspase-dependent pathway

A series of novel coumarin/2-cyanoacryloyl hybrids were prepared and evaluated for their in vitro anticancer activity. Among them, two analogs 5p and 5q showed promising antiproliferative activity against a panel of cancer cell lines, including A549, H157

Synthesis and Antibacterial Activity Evaluation of Novel (E)-4-(4-((arylidene)amino)phenoxy)coumarin Derivatives

A series of novel (E)-4-(4-((arylidene)amino)phenoxy)coumarin derivatives were synthesized from 4-hydroxycoumarin in three step reactions, and their antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas citri subsp. Citri (X

The legend of 4-aminocoumarin: Use of the Delepine reaction for synthesis of 4-iminocoumarin

Use of the Delepine reaction for synthesis of 4-aminocoumarin from 4-chlorocoumarin was not successful. The product was 4-iminocoumarin instead of 4-aminocoumarin. The 4-iminocoumarin was characterized by elemental analysis and spectral studies (FT-IR, s

Novel curcumin analogue hybrids: Synthesis and anticancer activity

In this study, twenty curcumin analogue hybrids as potential anticancer agents through regulation protein of TrxR were designed and synthesized. Results of anticancer activity showed that 5,7-dimethoxy-3-(3-(2-((1E, 4E)-3-oxo-5-(pyridin-2-yl)penta-1,4-dien-1- yl)phenoxy)propoxy)-2-(3,4,5-trimethoxyphenyl)-4H-chromen-4-one (compound 7d) could induce gastric cancer cells apoptosis by arresting cell cycle, break mitochondria function and inhibit TrxR activity. Meanwhile, western blot revealed that this compound could dramatically up expression of Bax/Bcl-2 ratio and high expression of TrxR oxidation. These results preliminarily show that the important role of ROS mediated activation of ASK1/MAPK signaling pathways by this title compound.

CHIRALITY SENSING WITH MOLECULAR CLICK CHEMISTRY PROBES

The present invention relates to an analytical method that includes providing a sample potentially containing a chiral analyte that can exist in stereoisomeric forms, and providing a probe selected from the group consisting of coumarin-derived Michael acceptors, dinitrofluoroarenes and analogs thereof, arylsulfonyl chlorides and analogs thereof, arylchlorophosphines and analogs thereof, aryl halophosphites, and halodiazaphosphites. The sample is contacted with the probe under conditions to permit covalent binding of the probe to the analyte, if present in the sample; and, based on any binding that occurs, the absolute configuration of the analyte in the sample, and/or the concentration of the analyte in the sample, and/or the enantiomeric composition of the analyte in the sample is/are determined. The probe may be a coumarin-derived Michael acceptor, a di nitrofluoroarene or analog thereof, an arylsulfonyl chloride or analog thereof, an arylchlorophosphine or analog thereof, an aryl halophosphite, or a halodiazaphosphite.

Design, synthesis and biological evaluation of novel coumarin-based hydroxamate derivatives as histone deacetylase (HDAC) inhibitors with antitumor activities

A series of novel coumarin-based hydroxamate derivatives were designed and synthesized as histone deacetylase inhibitors (HDACis). Selective compounds showed a potent HDAC inhibition with nM IC50 values, with the best compound (10e) being nearly 90 times more active than vorinostat (SAHA) against HDAC1. Compounds 10e and 11d also increased the levels of acetylated histone H3 and H4, which is consistent with their strong HDAC inhibition. In addition, 10e and 11d displayed a higher potency toward human A549 and Hela cancer cell lines compared with SAHA. Moreover, 10e and 11d significantly arrested A549 cells at the G2/M phase and enhanced apoptosis. Molecular docking studies revealed the possible mode of interaction of compounds 10e and 12a with HDAC1. Our findings suggest that these novel coumarin-based HDAC inhibitors provide a promising scaffold for the development of new potential cancer chemotherapies.