6-Hydroxy-1-tetralone

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Cat Number

INT3470506

CAS Number

3470-50-6

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Product Detail Description Scientific Support Customer Q&A

CAS Number

3470-50-6

Storage

Room temperature

Synonyms

6-Hydroxy-3,4-dihydronaphthalen-1(2H)-one

Molecular Formula

C10H10O2

Molecular Weight

162.19

Smiles

C1(=O)C2=C(C=C(O)C=C2)CCC1

Appearance

Off-white solid

Melting Point

154-157℃

Boiling Point

358℃

Relative Density

1.24

pKa

8.22

General Description

6-Hydroxy-1-tetralone (also called 6-hydroxy-3,4-dihydronaphthalen-1(2H)-one) is a tetralone (tetrahydronaphthalenone) bearing a phenolic hydroxyl group at the C-6 position of the bicyclic ring system. The cyclohexanone ring fused to the benzene ring creates a 1-tetralone (alpha-tetralone) pharmacophore. The phenolic hydroxyl at C-6 is available for O-alkylation, O-acylation, and oxidative coupling reactions, while the ketone at C-1 is a site for reduction, Wittig, and Grignard reactions.

Mechanism of Action

6-Hydroxy-1-tetralone functions as a key intermediate in the synthesis of naphthalene derivatives and aromatic polyketides. The ketone can be reduced to the corresponding alcohol (tetralol), converted to an exocyclic double bond via Wittig reaction, or undergo aldol condensation. The phenolic hydroxyl enables O-alkylation (to form aryl alkyl ethers) or O-acylation (to form aryl esters). The 6-hydroxy substitution pattern is common in tamoxifen analogs and anthracycline synthesis.

Application

6-Hydroxy-1-tetralone is used as an intermediate in the synthesis of tamoxifen and related selective estrogen receptor modulators (SERMs), anthracycline antibiotics (doxorubicin, daunorubicin), and naphthoquinone derivatives. The tetralone scaffold is found in compounds targeting estrogen receptors, protein kinases, and microtubules. It is also used in the synthesis of dyes and organic semiconductors.

6-Hydroxy-1-tetralone was synthesized as a key intermediate in the preparation of α-tetralone derivatives. It was obtained by hydrolysis of 6-methoxy-1-tetralone using anhydrous AlCl₃ in toluene under reflux. The compound was then reacted with various arylalkyl bromides in the presence of K₂CO₃ in refluxing acetone to yield the target compounds 6a–6o. When evaluated as a monoamine oxidase (MAO) inhibitor, 6-hydroxy-1-tetralone showed weak activity. Its IC₅₀ values were 43.8 ± 3.3 μM against MAO-A and 66.4 ± 13.6 μM against MAO-B.

Fig. 1 Synthetic route to the a-tetralone derivatives 6a–o. (Legoabe L J.; et al. 2014)

References

Legoabe L J, et al. α-Tetralone derivatives as inhibitors of monoamine oxidase. Bioorganic & medicinal chemistry letters, 2014, 24(12): 2758-2763.

What is the recommended storage condition for 6-Hydroxy-1-tetralone?

It should be stored at controlled room temperature in a well-sealed container, protected from moisture and direct light, to maintain its chemical integrity throughout the shelf life.

Can we obtain batch-specific analytical data for 6-Hydroxy-1-tetralone?

Batch-specific COA documents are standard with every shipment. Additional analytical reports, including HPLC chromatograms or spectral data, may be provided upon request.

What functional groups in 6-Hydroxy-1-tetralone are available for further chemical modification?

The specific reactive handles present in this intermediate can be confirmed by reviewing the technical data sheet. Our team can provide structural and reactivity information relevant to your synthetic route.

Is 6-Hydroxy-1-tetralone available in high-chemical-purity grade for pharmaceutical synthesis?

Yes, it is supplied in high chemical purity grades suitable for demanding pharmaceutical intermediate applications. Specifications and analytical data are available upon request.

Does your company offer custom packaging for 6-Hydroxy-1-tetralone?

Yes, custom pack sizes are available. Specific quantity requirements can be discussed directly with our team to align with your production or research scale.