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4-broMo-2-(trifluoroMethyl)pyriMidine, also known as 4-bromo-2-(trifluoromethyl)pyrimidine, is a synthetic compound that is commonly used in the chemical industry.
It is a white or slightly yellowish solid with a melting point of around 160-165°C.
The molecule has a linear structure and contains a bromine atom bonded to a carbon atom, which is in turn bonded to a nitrogen atom and a carbon atom.
The nitrogen atom is bonded to two carbon atoms and a hydrogen atom, while the carbon atom is bonded to two other carbon atoms and a trifluoromethyl group.
There are several synthetic routes that can be used to synthesize 4-broMo-2-(trifluoroMethyl)pyriMidine, each with its own advantages and disadvantages.
Some of the most common methods include:
- The Yaish-Wang method: This method involves the condensation of 2,6-dimethylpyridine with 2,6-dimethylnicotinamide in the presence of a solvent such as dichloromethane or chloroform.
The reaction is then followed by treating the resulting compound with a solution of n-butyllithium in hexane, which reduces the nicotinamide moiety to form the desired product. - The DuBois method: This method involves the reduction of 4-bromo-2-(trifluoromethyl)aniline using a reducing agent such as lithium aluminum hydride (LiAlH4) in the presence of a solvent such as ether or hexane.
The resulting compound is then treated with a base such as sodium hydroxide to neutralize the remaining bromine atom. - The Matsushita method: This method involves the reaction of 2-chloro-4-fluoropyrimidine with sodium hydride in the presence of a solvent such as N,N-dimethylacetamide.
The resulting compound is then treated with a base such as sodium hydroxide to convert the hydride ion to the desired product. - The Honda method: This method involves the reaction of 2-chloro-4-fluoropyrimidine with 2-dimethylaminoethanol in the presence of a condensation agent such as dicyclohexylcarbodiimide (DCC) and hydroxycoumarin.
The resulting compound is then treated with a base such as sodium hydroxide to form the desired product.
Each of these methods has its own advantages and disadvantages, and the choice of method will depend on the specific needs of the synthetic process.
For example, the Yaish-Wang method is generally considered to be the most efficient and convenient method for preparing 4-broMo-2-(trifluoroMethyl)pyriMidine, as it yields high yields of the desired product with a relatively simple reaction sequence.
However, this method requires the use of expensive and hazardous reagents such as lithium aluminum hydride and n-butyllithium, which can increase the overall cost and safety risk of the synthesis.
On the other hand, the Matsushita method is relatively simple and safe to perform, as it involves the use of lower molecular weight reagents such as sodium hydride and 2-dimethylaminoethanol.
However, this method requires longer reaction times and higher temperatures, which can result in lower yield and purity of the desired product.
Overall, the choice of synthetic route for 4-broMo-2-(trifluoroMethyl)pyriMidine will depend on a variety of factors, including the desired yield, purity, cost, and safety considerations of the synthesis.
It is important for