Chemistry
Organic Building Blocks
Trifluoromethyls
The trifluoromethyl group (-CF3) is a functional group consisting of three fluorine atoms bonded to a carbon atom that is also attached to the molecule it is a part of. Its name is derived from the methyl group (-CH3) by replacing all three hydrogen atoms with fluorine atoms.
The trifluoromethyl group is present in specific pharmaceuticals, medications, and naturally occurring fluorocarbon compounds that are synthesized abiotically.
Adding a trifluoromethyl group can also modify the solubility of molecules that contain other functional groups, providing another method for fine-tuning the physical properties of the molecule.
One common strategy in medicinal chemistry is to replace a functional group in a molecule with a bioisostere, a group that has similar physical and chemical properties but can improve pharmacokinetics or pharmacodynamics. The trifluoromethyl group is a popular bioisostere for replacing a chloride or methyl group, as it can enhance metabolic stability, lipophilicity, and receptor binding affinity.
The trifluoromethyl group is known for its significant electronegativity, which is typically considered to be intermediate between the electronegativities of fluorine and chlorine.
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1-(Trifluoromethyl)cyclobutanecarboxylic acid
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2-Amino-N-(2,2,2-trifluoroethyl)acetamide hydrochloride
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Ethyl 5,5,5-trifluoro-2,4-dioxopentanoate
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(S)-2-Amino-3,3,3-trifluoropropan-1-ol hydrochloride
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Ethyl 1-(trifluoromethyl)cyclopropanecarboxylate
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2-Chloro-N-(2,2,2-trifluoroethyl)acetamide
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2-Methyl-2-(trifluoromethylsulfonamido)propyl methacrylate
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1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine
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1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane
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(R)-1,1,1-Trifluoro-2-butylamine hydrochloride
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(1R)-1-(Trifluoromethyl)ethylamine hydrochloride
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(S)-1,1,1-Trifluoropropan-2-amine hydrochloride
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(S)-3,3,3-Trifluoro-2-hydroxy-2-methylpropanoic acid
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1-(4-Trifluoromethylphenyl)piperidin-4-ol
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N-Methyl-2,2,2-trifluoroethylamine Hydrochloride