3-(Fluoromethyl)azetidine hydrochloride
[CAS# 1642298-59-6]

Identification

• Classification: Organic raw materials >> Heterocyclic compound
• Name: 3-(Fluoromethyl)azetidine hydrochloride
• Molecular Formula: C₄H₉ClFN
• Molecular Weight: 125.57
• CAS Registry Number: 1642298-59-6
• EC Number: 892-875-8
• SMILES: C1C(CN1)CF.Cl

Safety Data

• Hazard Symbols: GHS07 Warning
• Hazard Statements: H315-H319-H335
• Precautionary Statements: P261-P264-P264+P265-P271-P280-P302+P352-P304+P340-P305+P351+P338-P319-P321-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Discovory and Applicatios

3-(Fluoromethyl)azetidine hydrochloride is a chemical compound containing an azetidine ring, a four-membered nitrogen-containing heterocycle, with a fluoromethyl group (-CH2F) attached at the 3-position of the ring. The hydrochloride form of the compound is a salt, where the nitrogen of the azetidine ring is protonated and paired with a chloride ion.

The discovery and development of this compound, along with other azetidine derivatives, is significant in the field of medicinal chemistry. Azetidine-based compounds are known for their diverse biological activities, making them important scaffolds for drug discovery. The incorporation of the fluoromethyl group at the 3-position is particularly interesting because the fluorine atom, due to its electronegativity, can modify the compound’s electronic properties, influence its interaction with biological targets, and affect its pharmacokinetics, such as its stability and bioavailability.

3-(Fluoromethyl)azetidine hydrochloride has been studied for its potential applications in various therapeutic areas. The azetidine ring itself has been a focal point for drug design, as it is a rigid structure that can lead to improved binding interactions with certain biological receptors or enzymes. The introduction of the fluoromethyl group enhances the chemical stability of the molecule and may increase its potency by affecting receptor binding or inhibiting enzymatic activity.

In the pharmaceutical industry, fluorinated compounds are often considered for their improved metabolic stability, which can lead to longer durations of action in vivo. The incorporation of a fluoromethyl group is a strategy used to modify the properties of biologically active molecules, making them more resistant to metabolic degradation while still maintaining their ability to interact with biological targets.

The compound could also serve as an intermediate in the synthesis of more complex molecules. By altering the azetidine ring or introducing additional functional groups, researchers can generate a wide array of derivatives with varying biological activities. These modifications can be targeted toward developing new treatments for a range of diseases, including those caused by bacterial infections, cancers, and other disorders where molecular inhibition or activation is required.

Moreover, the compound may also find utility in the field of agrochemicals, where azetidine derivatives have shown promise as herbicides or insecticides. The unique properties of fluoromethyl groups, such as increased lipophilicity and the potential to cross biological membranes more easily, may enhance the performance of these compounds in agricultural applications.

In summary, 3-(Fluoromethyl)azetidine hydrochloride is a valuable compound in the context of drug discovery and agrochemical development. Its combination of an azetidine ring and a fluoromethyl group makes it a useful scaffold for designing bioactive molecules with improved stability, potency, and selectivity.

References

2025. A practical synthesis of YZD-7082B, a novel orally bioavailable selective estrogen receptor degrader (SERD) for the treatment of ER+ breast cancer. Molecular Diversity, 29(1).
URL: https://pubmed.ncbi.nlm.nih.gov/40089967