5117-56-6

Basic information

• Product Name: 3,4-dichloro-2H-chromen-2-one
• CAS NO: 5117-56-6
• Molecular Formula: C₉H₄Cl₂O₂
• Molecular Weight: 215.0329
• Mol File: 5117-56-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 330.7°C at 760 mmHg
• Flash Point: 151.2°C
• Density: 1.53g/cm³
• Vapor Pressure: 0.000163mmHg at 25°C
• Refractive Index: 1.627
• CAS DataBase Reference: 3,4-dichloro-2H-chromen-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dichloro-2H-chromen-2-one(5117-56-6)
• EPA Substance Registry System: 3,4-dichloro-2H-chromen-2-one(5117-56-6)

Safety Data

• Hazardous Substances Data: 5117-56-6(Hazardous Substances Data)

Usage

General Description

3,4-dichloro-2H-chromen-2-one, also known as coumachlor, is a chemical compound with a molecular formula of C9H4Cl2O2. It is a derivative of coumarin and is commonly used as a rodenticide, as it acts as an anticoagulant by inhibiting the enzyme vitamin K epoxide reductase. This prevents the blood from clotting properly, leading to internal bleeding and eventual death in rodents. Due to its toxic effects on both rodents and humans, it is considered a hazardous substance and should be handled with caution. Additionally, exposure to high levels of 3,4-dichloro-2H-chromen-2-one can have harmful effects on the liver and may cause skin and eye irritation. Therefore, it is important to use protective equipment and follow safety guidelines when working with this compound.

Upstream product

• 23029-98-3 3-Chlor-4-hydroxy-2-oxo-2H<1>benzopyran 
• 1888-71-7 perchloropropene 
• 108-95-2 phenol 
• 7446-70-0 aluminium trichloride 
• 75-15-0 carbon disulfide 
• 17831-88-8 4-chloro-2H-1-benzopyran-2-one 

Downstream Products

• 36048-07-4 3-chloro-4-piperidino-coumarin 
• 100914-71-4 3-chloro-4-phenoxy-2-coumarin 
• 101726-84-5 4-benzylmercapto-3-chloro-coumarin 
• 1268825-47-3 12-phenyl-6H-chromeno[3,4-a]indolizin-6-one 

Relevant articles and documents

A Copper Halide Promoted Regioselective Halogenation of Coumarins Using N-Halosuccinimide as Halide Source

A safe, convenient, and regioselective synthesis of 3-halo coumarins using a metal halide (CuX 2 alone or with ZnX 2) promoted halogenation with N -halosuccinimide (NXS) as halide source is reported. The synthesis involved the steady in situ generation of highly reactive positive halogen (X +) by the coordination of copper or zinc with the N -halosuccinimide and subsequent electrophilic aromatic substitution of the electron-deficient coumarins. This procedure works well also for the halogenation of less electron-rich naphthoquinones, flavones, and methoxypsoralen in moderate to quantitative yields. This protocol features simple experimental conditions using readily available inexpensive reagents and provides a convenient approach to the chlorination or bromination of some useful heteroaromatic compounds.

A metal-free one-pot synthesis of benzo[: C] chromen-6-ones from 3,4-dichlorocoumarins and butadienes using tandem photo-thermal-photo reactions

An efficient, simple and versatile synthesis of biologically valuable benzo[c]chromen-6-ones is achieved using a tandem photo-thermal-photo reaction sequence starting from 3,4-dichlorocoumarins and a 1,3-butadiene. In this concise one-pot protocol, neither metal catalyst nor peroxide promoter is needed and the products can be purified through simple recrystallization in most cases. The synthesis consists of a reaction sequence of photo-induced [4 + 2] and [2 + 2] cycloadditions, silica gel promoted elimination of HCl and electrocyclic cyclobutene ring opening followed by a photo-induced 6π electrocyclization. The reactions proceed well with a range of dichlorocoumarins and some typical butadienes to provide the corresponding annulated products in 70-80% yield.