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

General 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 primarily used in the synthesis of various pharmaceuticals and agrochemicals. It is also known for its potential biological activities, including antifungal, antibacterial, and antitumor properties. Its unique chemical structure makes it a valuable intermediate in the production of various functionalized coumarin derivatives with diverse biological and pharmacological properties.

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

Downstream Products

• 35817-27-7 4-ethoxy-2H-chromen-2-one 
• 91-64-5 coumarin 
• 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 
• 145982-70-3 (E)-3-butyl-1-chloro-1-(o-hydroxyphenyl)hept-1-en-3-ol 
• 134817-32-6 4-(3-oxo-1-cyclohexenyl)-coumarin 
• 136538-14-2 1,1,6,6-Tetraphenyl-hexa-2,4-diyne-1,6-diol; compound with 4-chloro-chromen-2-one 
• 156742-60-8 4-(2-oxo-2-phenyl-ethylamino)-2H-1-benzopyran-2-one 
• 5101-44-0 2-ethynyl-phenol 
• 145982-76-9 3-ethyl-1-(o-hydroxyphenyl)pent-1-yn-3-ol 
• 145982-72-5 (Z)-3-ethyl-5-(o-hydroxyphenyl)hept-4-en-3-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.

Novel conjugates of podophyllotoxin and coumarin: Synthesis, cytotoxicities, cell cycle arrest, binding CT DNA and inhibition of Topo IIβ

A series of conjugates of podophyllotoxin and coumarin were prepared using the click reaction, and their cytotoxicities against A549, HepG2, HeLa, and LoVo cells were evaluated. Among them, compound 14e exhibited the strongest cytotoxicities against these cancer cells with IC50 values of 4.9–17.5 μM. Furthermore, 14e disrupted microtubules and induced cell cycle arrest at G1 phase by regulating P21 and Cyclin D1 in LoVo cells. In addition, 14e bond CT DNA and selectively inhibited Topo IIβ over Topo IIα. Molecular docking model showed that 14e appeared to form stable hydrogen bonds with several DNA bases and residue Gln778. Taken together, these conjugates have the potential to be developed as anti-tumor drugs.