38169-98-1

Usage

Uses

Used in Pharmaceutical Industry:
5-Chlorocoumarin is used as an active pharmaceutical ingredient for its anti-inflammatory, analgesic, and anti-coagulant properties, contributing to the development of drugs that address these conditions.
Used in Drug Synthesis:
5-Chlorocoumarin is utilized as a building block in the synthesis of more complex pharmaceutical compounds, leveraging its versatile reactivity and functional groups to create a wide range of medicinal products.
Used in Cancer Research:
5-Chlorocoumarin is studied for its potential anti-cancer properties, with ongoing research aimed at understanding its effects on various types of cancer and its potential integration into cancer treatment strategies.
Used in Microbiology:
5-Chlorocoumarin is also being investigated for its anti-microbial properties, which could lead to its use in the development of new antimicrobial agents to combat resistant strains of bacteria and other pathogens.

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 
• 46275-03-0 methyl (2E)-3-(2,6-dichlorophenyl)prop-2-enoate 
• 108-24-7 acetic anhydride 
• 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 
• 3260-87-5 3-chloro-o-cresol 
• 617-48-1 malic acid 
• 105786-77-4 3-Ethoxyacrylsaeure-3-chlorphenylester 
• 59507-35-6 methyl (2Z)-3-(2,6-dichlorophenyl)prop-2-enoate 

Downstream Products

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

Relevant academic research and scientific papers

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.

A quick and advantageous synthesis of 2H-1-benzopyran-2-ones unsubstituted on the pyranic nucleus

The synthesis of 2H-1-benzopyran-2-ones (coumarins) unsubstituted on the pyranic nucleus was realized by condensation of malic acid and phenols under mild conditions. A short reaction time, improved yields, good purity of the products, and an easy clean experimental protocol are the advantages of this procedure. Georg Thieme Verlag Stuttgart.

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.

Photocyclization of Ortho-Substituted Cinnamic Acids

Mono and di (i.e. 2,6) o-chloro- and o-methoxycinnamic acids undergo photocyclization to give the corresponding coumarins.The reaction occurs in aqueous and organic media, with a prototypical reaction giving evidence of being favored at pH > 6.Cyclization of the dimethoxy acid is relatively inefficient (Φ for the PSS = 0.0015), and a photostationary state of the cis/trans acids is formed early into the reaction.The photocyclization of the dichloro analog is more efficient (Φ exceeds 0.04) and therefore time dependent since product formation competes with trans/cis isomerization.Methyl o-chlorocinnamate also photocyclizes (Φ for the PSS = 0.0022 in acetonitrile) but the o-methoxy ester is virtually photoinert.It is proposed that the acid photocyclizes through intramolecular nucleophilic attack by the carboxylate group followed by heterolysis of the nucleofuge.Methyl o-chlorocinnamate appears to photocyclize through a cycloaddition of the carbonyl group followed by homolysis of the Cl and Me moieties, possibly through the intermediacy of a ketene as proposed by earlier workers.

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.

Photocyclization of 2,6-Dichlorocinnamic Acid Derivatives to 5-Chlorocoumarin

On UV irradation, 2,6-dichlorocinnamic acid and its esters undergo photocyclization with elimination of the elements of HCl or RCl (R = alkyl or aryl) to yield 5-chlorocoumarin (2); amide derivatives yield the corresponding imino analogues.Low-temperature

SYNTHESIS AND REACTIONS OF SOME CHLORO-2,2-DIMETHYLCHROMENS

5-, 6-, 7-, and 8-Chloro-2,2-dimethylchromens have been prepared from the corresponding chlorocumarin and their conversion into the 3,4-dihalogenochroman derivatives is described.The 4-halogen atom is shown to be the more susceptible to hydrolysis by conv