38169-98-1

Basic information

• Product Name: 5-Chlorocoumarin
• Synonyms: 5-Chlorocoumarin;5-chloro-2H-chromen-2-one;5-chlorochromen-2-one
• CAS NO: 38169-98-1
• Molecular Formula: C₉H₅ClO₂
• Molecular Weight: 180.5878
• Mol File: 38169-98-1.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 332 °C at 760 mmHg
• Flash Point: 179.8 °C
• Appearance: /
• Density: 1.399 g/cm³
• Vapor Pressure: 0.00015mmHg at 25°C
• Refractive Index: 1.608
• CAS DataBase Reference: 5-Chlorocoumarin(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Chlorocoumarin(38169-98-1)
• EPA Substance Registry System: 5-Chlorocoumarin(38169-98-1)

Safety Data

• Hazardous Substances Data: 38169-98-1(Hazardous Substances Data)

Usage

General Description

5-Chlorocoumarin is a chemical compound that belongs to the coumarin family, which is often used in various pharmaceutical and medicinal applications. It is a white crystalline solid with a molecular formula of C9H6O3Cl. 5-Chlorocoumarin is known for its anti-inflammatory, analgesic, and anti-coagulant properties, making it a valuable ingredient in the production of drugs targeting these conditions. Additionally, it has also been studied for its potential anti-cancer and anti-microbial properties. 5-Chlorocoumarin is commonly used as a building block in the synthesis of more complex pharmaceutical compounds due to its versatile reactivity and functional groups. Overall, 5-Chlorocoumarin is an important chemical in the pharmaceutical industry with promising potential for a wide range of medicinal applications.

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

Upstream product

• 4071-85-6 trimetylsilylketene 
• 18362-30-6 2-chloro-6-hydroxybenzaldehyde 
• 59507-35-6 methyl (2Z)-3-(2,6-dichlorophenyl)prop-2-enoate 
• 46275-03-0 methyl (2E)-3-(2,6-dichlorophenyl)prop-2-enoate 
• 108-24-7 acetic anhydride 
• 105786-77-4 3-Ethoxyacrylsaeure-3-chlorphenylester 
• 20595-49-7 (2E)-3-(2,6-dichlorophenyl)prop-2-enoic acid 
• 20595-50-0 cis-2,6-Dichlorocinnamic acid 
• 108-43-0 3-monochlorophenol 
• 617-48-1 malic acid 
• 3260-87-5 3-chloro-o-cresol 

Downstream Products

• 85995-42-2 2-chloro-6-methoxy-cis-cinnamic acid 

Relevant articles and documents

Gold(I)-Catalyzed Intramolecular Hydroarylation of Phenol-Derived Propiolates and Certain Related Ethers as a Route to Selectively Functionalized Coumarins and 2 H-Chromenes

Methods are reported for the efficient assembly of a series of phenol-derived propiolates, including the parent system 56, and their Au(I)-catalyzed cyclization (intramolecular hydroarylation) to give the corresponding coumarins (e.g., 1). Simple syntheses of natural products such as ayapin (144) and scoparone (145) have been realized by such means, and the first of these subject to single-crystal X-ray analysis. A related process is described for the conversion of propargyl ethers such as 156 into the isomeric 2H-chromene precocene I (159), a naturally occurring inhibitor of juvenile hormone biosynthesis.

Further studies of orientation effects in the Pechmann synthesis of coumarins

A study of orientation effects in the Pechmann synthesis with some meta-substituted phenols is presented. Variation of the reaction conditions with malic acid indicates that whilst the proportion of 5-chlorocoumarin diminishes at higher temperatures that of 5-methoxycoumarin increases, accompanied by cleavage of the ether function under certain conditions. Reactions with ethyl acetoacetate give only the 4,7-isomers. Peri-substituent effects in 1 H and 13C NMR spectroscopy have been used for product identification.

Enolethers, XVIII. - A Simple Synthesis of Coumarins

In boiling 1,2-dichloroethane 3-ethoxyacryloyl chloride (1) reacts with phenols 2 to yield 3-ethoxyacrylates 3, which by treatment with conc. sulfuric acid/10percent SO3 cyclize to give coumarins 9 in good yields.The methoxy-substituted compounds 3d and 3k do not react to coumarins 9 with H2SO4/SO3 but with POCl3/H2O at room temperature.