6-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one
[CAS# 214045-84-8]

Identification

• Classification: Pharmaceutical intermediate >> Heterocyclic compound intermediate >> Quinoline compound
• Name: 6-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one
• Synonyms: 6-fluoro-3,4-dihydro-2H-isoquinolin-1-one
• Molecular Formula: C₉H₈FNO
• Molecular Weight: 165.16
• CAS Registry Number: 214045-84-8
• EC Number: 836-816-6
• SMILES: C1CNC(=O)C2=C1C=C(C=C2)F

Properties

• Density: 1.2±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.543, Calc.^*
• Boiling Point: 404.1±45.0 °C (760 mmHg), Calc.^*
• Flash Point: 198.2±28.7 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H315-H319-H335
• Safety 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

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2A	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335

Discovery and Applications

6-Fluoro-1,2,3,4-tetrahydroisoquinolin-1-one is a fluorinated heterocyclic compound belonging to the class of tetrahydroisoquinolinones. The incorporation of a fluorine atom at the sixth position of the isoquinolinone core influences its electronic properties, metabolic stability, and potential biological activity. The tetrahydroisoquinoline scaffold is widely studied in medicinal chemistry due to its presence in numerous bioactive molecules and natural alkaloids.

The discovery of fluorinated tetrahydroisoquinolinones is closely related to research in synthetic organic chemistry and drug discovery. Fluorine substitution is often employed to modify the physicochemical properties of a molecule, such as lipophilicity and binding affinity to biological targets. The synthesis of 6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-one typically involves selective fluorination strategies and cyclization reactions that form the tetrahydroisoquinoline ring system.

One of the key applications of 6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-one is in pharmaceutical research. The tetrahydroisoquinoline core is found in various pharmacologically active compounds, including those with activity against neurological disorders, cardiovascular diseases, and cancer. Fluorinated derivatives of tetrahydroisoquinolinones have been explored for their potential role in modulating enzyme activity and receptor interactions.

In addition to pharmaceuticals, fluorinated heterocycles have been investigated for their applications in agrochemicals and material science. The presence of fluorine can enhance the stability and efficacy of active compounds in pest control and crop protection. Furthermore, tetrahydroisoquinoline derivatives have been used in the design of functional materials, including optoelectronic devices and molecular probes.

The synthesis and study of 6-fluoro-1,2,3,4-tetrahydroisoquinolin-1-one continue to be of interest in organic and medicinal chemistry. Advances in fluorination methods and catalytic processes have improved the accessibility of such fluorinated heterocycles, expanding their potential applications in various scientific and industrial fields.

References

(2022). Ulk1/2 inhibitors and their use thereof. WO-2022214869-A2, 2022-10-13.
Priority Date: 2021-04-07.

(2021). Substituted quinazoline compound, and preparation method therefor, pharmaceutical composition thereof, and use thereof. WO-2021254464-A1, 2021-12-23.
Priority Date: 2020-06-19.

(2021). Egfr inhibitor and preparation method and use thereof. WO-2021238827-A1, 2021-12-02.
Priority Date: 2020-05-25.