6-Fluoro-1-tetralone
[CAS# 703-67-3]

Identification

• Classification: Organic raw materials >> Ketone compound
• Name: 6-Fluoro-1-tetralone
• Synonyms: 6-Fluoro-3,4-dihydro-2H-naphthalen-1-one
• Molecular Formula: C₁₀H₉FO
• Molecular Weight: 164.18
• CAS Registry Number: 703-67-3
• EC Number: 826-060-5
• SMILES: C1CC2=C(C=CC(=C2)F)C(=O)C1

Properties

• Density: 1.2±0.1 g/cm³ Calc.^*
• Boiling point: 269.5±29.0 ºC 760 mmHg (Calc.)^*
• Flash point: 102.3±14.5 ºC (Calc.)^*
• Index of refraction: 1.543 (Calc.)^*

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

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

Hazard Classification

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

Discovory and Applicatios

6-Fluoro-1-tetralone is a fluorinated derivative of 1-tetralone, a bicyclic aromatic ketone belonging to the tetralin series. It consists of a benzene ring fused to a hydrogenated cyclohexanone ring, with a fluorine atom located at the sixth position of the aromatic ring, making it a member of the class of halogenated tetralones. Its structure combines an aromatic system with a reactive carbonyl group, and this combination has made substituted tetralones important intermediates in chemical synthesis. The parent compound 1-tetralone was first obtained during investigations into partially hydrogenated aromatic hydrocarbons in the late nineteenth and early twentieth century, when reductions of naphthalene derivatives were explored. Halogenated derivatives, including fluorinated analogues, were later prepared through electrophilic halogenation or via functional group transformations, and they appeared in research as tools for building more complex organic molecules.

Interest in fluorinated tetralones developed as fluorine chemistry became widespread in the second half of the twentieth century, particularly when investigators began examining the influence of fluorine substitution on reactivity, biological activity, and physicochemical properties. The presence of fluorine on an aromatic ring affects electron distribution and can change the behavior of a compound in oxidative, reductive, and nucleophilic aromatic substitution processes. Work on selective monofluorination of tetralone derivatives led to the preparation of 6-fluoro-1-tetralone by adapting established aromatic fluorination methods, including halogen exchange and direct fluorination of activated precursors. This enabled controlled production of the compound for laboratory and industrial use.

6-Fluoro-1-tetralone has been used primarily as an intermediate in organic synthesis, particularly in the preparation of fluorinated molecules for pharmaceutical and agrochemical research. The ketone group allows conversion into alcohols, amines, and other functional groups, while the fluorine atom remains stable under many reaction conditions. Reduction of the carbonyl group gives access to fluorinated tetralols, and oxidation can yield related aromatic acids or quinone-type structures. The compound can undergo condensation, alkylation, and ring formation, providing a pathway to molecules containing rigid bicyclic scaffolds. Researchers have used this compound as a starting material for preparing analogues of bioactive compounds, enabling systematic investigation of structure-activity relationships where the influence of fluorine substitution is of interest.

Fluorinated tetralones have been used to generate structural cores for receptor ligands, enzyme inhibitors, and central nervous system–active molecules, reflecting the importance of the bicyclic motif in medicinal chemistry. Fluorine substitution can affect lipophilicity, metabolic stability, binding affinity, and conformation, making compounds like 6-fluoro-1-tetralone valuable in the design of derivatives in which subtle electronic effects are desired. These transformations have also appeared in the development of synthetic building blocks for research into materials chemistry, where halogenated aromatic ketones play a role in the preparation of polymers, dyes, and liquid-crystal precursors.

Because of the reactive carbonyl functionality, 6-fluoro-1-tetralone can participate in enolate chemistry, facilitating the introduction of substituents at the position adjacent to the ketone. This reactivity was an important factor in its adoption in synthetic sequences designed to assemble complex cyclic or polycyclic products. The compound has been used in multi-step syntheses in which it acts as a substrate for carbon–carbon bond formation, heterocycle construction, and the creation of functionalized polyaromatic systems. In addition, the fused-ring structure resembles motifs found in naturally occurring compounds, which has supported its use in the synthesis of natural product analogues.

In summary, 6-fluoro-1-tetralone emerged from the systematic study of substituted tetralones following the initial preparation of 1-tetralone in the early explorations of partially hydrogenated aromatic hydrocarbons. Its applications are concentrated in synthetic organic chemistry, where it is used as a precursor to diverse fluorinated molecules, including intermediates for pharmaceuticals, agrochemicals, and functional materials. Its combination of a bicyclic scaffold, a ketone group, and a fluorine atom provides a versatile platform for chemical transformations, enabling the preparation of structurally and electronically varied compounds for research and development.

References

2012. β-Iminoenamine-BF2 Complexes: Aggregation-Induced Emission and Pronounced Effects of Aliphatic Rings on Radiationless Deactivation. Chemistry � An Asian Journal, 7(11).
DOI: 10.1002/asia.201200477