Chemistry Organic Building Blocks Difluoromethyls

Difluoromethyls

The difluoromethyl group is known to be isosteric and isopolar to a hydroxyl group, meaning that it has a similar size and electronic distribution, and can act as a lipophilic hydrogen bond donor.

One strategy to reduce lipophilicity and prevent potential glucuronidation is to use the difluoromethyl group (CHF2) as a bioisostere of hydrogen bond donors such as OH, SH, and NH2. This group also serves as a hydrogen bond donor and can be used in medicinal chemistry to modify the pharmacokinetic properties of a molecule.

The −CF2H group is a useful isostere for the carbinol, thiol, hydroxamic acid, or amide functional groups due to its increased lipophilicity. As a result, the CF2H group is frequently used to replace hydroxyl, amino, and thio substituents in lead structures during drug discovery.

The CF2H group, which is composed of two fluorine atoms and one hydrogen atom, is gaining attention for its distinctive capability to function as a lipophilic hydrogen bond donor. This property makes it a promising bioisostere for hydroxyl, amino, or thiol groups, and is the reason why researchers are becoming increasingly interested in its potential applications.

In contrast to the lipophilic trifluoromethyl (CF3) group, the difluoromethyl (CF2H) group possesses distinctive properties. It has a slight acidity and can participate in hydrogen-bonding interactions to enhance the binding affinity of biologically active compounds. As a result, the CF2H group is widely used in the development of pharmaceuticals and agrochemicals.

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(difluoromethyl)benzene 1-(difluoromethoxy)-2-fluorobenzene 1-(difluoromethyl)-2-fluorobenzene 1-bromo-2-(difluoromethyl)benzene 2-(difluoromethoxy)phenol 2-(difluoromethyl)pyridine 3-(difluoromethyl)pyridine 4-(difluoromethoxy)aniline 5-(difluoromethyl)-1H-pyrazole

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    1-(Difluoromethyl)cyclopropanecarboxylic acid

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    3-(Difluoromethyl)piperidine hydrochloride

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    2-(Difluoromethyl)pyrimidin-5-ol

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    2-(Difluoromethyl)pyrimidin-5-ol

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