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7-Benzyloxy-4-chloro-6-methoxy-quinoline, also known as BMQ, is a synthetic compound that has gained significant attention in the chemical industry due to its unique properties and diverse range of applications.
The synthesis of BMQ has been a topic of extensive research in the field of organic chemistry, and there are several synthetic routes available for the synthesis of this compound.
One of the most commonly used synthetic routes for the synthesis of BMQ is through the Horner-Wadsworth-Emmons (HWE) reaction.
This reaction involves the use of sodium hydride as a reagent to promote the reaction between benzyl bromide and chloroacetic acid, followed by the addition of potassium hydroxide to hydrolyze the resulting N-benzyl carbamate.
The resulting intermediate is then treated with methyl iodide to form the methoxy group, and Finally, a solution of BMQ in an appropriate solvent is treated with a base to hydrolyze the benzyl ether and form the final product.
Another synthetic route for the synthesis of BMQ is through the use of the Peterson oligomerization.
This reaction involves the use of a palladium catalyst to promote the reaction between two molecules of benzyl alcohol, which causes the formation of a polymer that can be hydrolyzed to form BMQ.
This method is considered to be more efficient than the HWE route, as it allows for the synthesis of larger quantities of BMQ with a higher degree of purity.
A third synthetic route for the synthesis of BMQ is through the use of the Dess-Martin periodinane.
This reaction involves the use of a zinc iodide and trifluoromethanesulfonic acid as a reagent to form the BMQ compound.
This method is considered to be relatively safe and efficient, and it does not require the use of any toxic or expensive reagents.
The synthesis of BMQ using these methods can vary depending on the specific conditions used, the purity of the starting materials and the desired yield of the final product.
However, regardless of the route taken, the final product is a white or off-white solid that is soluble in a variety of organic solvents.
The synthetic routes of BMQ vary, but the commonality is the final product, which is a valuable compound in the chemical industry due to its unique properties and diverse range of applications.
One of the main advantages of BMQ is its ability to act as an antagonist of the aryl hydrocarbon receptor (AhR), making it useful as a tool in the study of this receptor.
BMQ is also known to be a potent inhibitor of the activity of the CYP1A1 enzyme, which is involved in the metabolism of a wide variety of xenobiotics.
Additionally, BMQ has been shown to have anti-inflammatory and anti-tumor properties, making it a potential therapeutic agent for the treatment of a variety of diseases.
BMQ is widely used in the pharmaceutical industry for the development of new drugs.
It is also used in the agrochemical industry as a pesticide.
The compound is also used in research as a tool to study the AhR and other nuclear receptors, as well as in the study of enzyme kinetics and the mechanism of drug action.
In conclusion, the synthetic routes of 7-Benzyloxy-4-chloro-6-methoxy-quinoline are varied and depend on the desired yield and purity of the final product.
BMQ is used in a wide range of applications, including the pharmaceutical and agrochemical industries, and it is useful as a tool in the study of nuclear receptors and the mechanism of drug action.
Its unique properties make it a