7-Methoxy-1-tetralone
[CAS# 6836-19-7]

Identification

• Classification: Chemical reagent >> Organic reagent >> Polycyclic compound
• Name: 7-Methoxy-1-tetralone
• Synonyms: 7-methoxy-3,4-dihydro-2H-naphthalen-1-one
• Molecular Formula: C₁₁H₁₂O₂
• Molecular Weight: 176.21
• CAS Registry Number: 6836-19-7
• EC Number: 229-916-0
• SMILES: COC1=CC2=C(CCCC2=O)C=C1

Properties

• Melting point: 59-63 °C

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302-H315-H319-H332-H335
• Safety Statements: P261-P280-P305+P351+P338

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Chronic hazardous to the aquatic environment	Aquatic Chronic	3	H412

Discovery and Applications

7-Methoxy-1-tetralone is a methoxylated derivative of tetralone with a methoxy group at the seventh position of the tetralone skeleton. The compound is widely known for its applications in organic synthesis, especially in the pharmaceutical and fine chemicals industries.

7-Methoxy-1-tetralone was first synthesized in the mid-20th century during a study aimed at developing new intermediates for organic synthesis. It was found that the introduction of a methoxy group into the tetralone structure affects the reactivity and stability of the compound, making it a valuable building block for further chemical transformations. The synthesis usually involves the methylation of 1-tetralone, which is facilitated by various methoxylating agents under controlled conditions.

7-Methoxy-1-tetralone is mainly used in the fields of organic synthesis and medicinal chemistry: 7-Methoxy-1-tetralone is used as an intermediate in the synthesis of various drugs. Its structure can serve as a scaffold for the development of drugs targeting neurological diseases, such as antidepressants and antipsychotics. The methoxy group at the seventh position can be further modified to introduce different functional groups, resulting in new therapeutic agents.

In organic chemistry, 7-methoxy-1-tetralone is a valuable starting material for the synthesis of more complex molecules. Its reactivity allows for a variety of chemical modifications such as reduction, oxidation, and substitution reactions. This versatility makes it an important compound for researchers developing new synthetic routes and methods.

7-Methoxy-1-tetralone is used to synthesize natural products and their analogs. The tetralone structure is a common part in many natural compounds, and methoxy derivatives help to mimic or modify the natural structure. This application is essential for studying the biological activity of natural products and developing new bioactive compounds.

The methoxy group in 7-methoxy-1-tetralone can serve as a directing group in aromatic substitution reactions. This property has been used to synthesize a variety of aromatic compounds, allowing for regioselective functionalization. This makes it a useful reagent for the preparation of complex aromatic systems.

7-Methoxy-1-tetralone should be handled carefully in a well-ventilated area and with appropriate personal protective equipment. It is generally stable, but it should be stored away from strong oxidants and direct sunlight to prevent degradation.

References

2011. 7-Methoxy-3,4-dihydronaphthalen-1(2H)-one. Acta crystallographica. Section E, Structure reports online.
DOI: 10.1107/s1600536811020174

2022. Research progress in pharmacological activities and structure-activity relationships of tetralone scaffolds as pharmacophore and fluorescent skeleton. European Journal of Medicinal Chemistry.
DOI: 10.1016/j.ejmech.2021.113964

2023. Continuous-flow synthesis of 7-methoxy-1-tetralone: an important intermediate of (-)-Dezocine. Journal of Flow Chemistry.
DOI: 10.1007/s41981-023-00274-0