3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one: Properties & Applications
3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one: Properties & Applications
3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one is a phenolic cyclic ketone belonging to the tetralone family, featuring a free hydroxyl group at the 8-position that makes it a versatile intermediate in organic synthesis and pharmaceutical research.
- IUPAC Name
- 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one
- Common Synonym
- 8-Hydroxy-α-tetralone
- Molecular Formula
- C₁₀H₁₀O₂
- Molecular Weight
- 162.19 g/mol
- Functional Groups
- Phenolic hydroxyl, cyclic ketone (carbonyl)
- Aladdin SKU
- D698198
Chemical Structure and Key Properties
3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one, commonly referred to as 8-hydroxy-α-tetralone, is a bicyclic compound consisting of a partially saturated six-membered carbocyclic ring fused to a benzene ring bearing a phenolic hydroxyl substituent at the 8-position and a ketone carbonyl at the 1-position. Its molecular formula is C₁₀H₁₀O₂ with a molecular weight of approximately 162.19 g/mol.
The coexistence of a reactive carbonyl and a free phenolic hydroxyl group within the same scaffold imparts distinctive reactivity to this molecule. The phenolic –OH can participate in hydrogen bonding, O-alkylation, O-acylation, and oxidative transformations, while the ketone is amenable to nucleophilic additions, reductive amination, and condensation reactions. This dual functionality underpins the compound's value as a bifunctional building block.
Synthesis and Synthetic Utility
8-Hydroxy-α-tetralone can be accessed through several established synthetic routes. A classical approach involves the intramolecular Friedel–Crafts acylation of appropriately substituted phenylbutyric acid derivatives under Lewis acid catalysis, yielding the tetralone core in a single cyclization step. Alternatively, selective reduction or functional-group manipulation of naphthol precursors provides complementary access.
As a synthetic intermediate, 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one serves as a platform for constructing more complex polycyclic frameworks. The free hydroxyl group can be selectively protected or elaborated prior to further transformations at the ketone, enabling orthogonal manipulation of both reactive sites. Researchers routinely employ this compound in the preparation of tricyclic natural product analogs, substituted tetralones, and fused heterocyclic systems relevant to medicinal chemistry programs.
Research Applications
The compound occupies an important niche in medicinal chemistry and total synthesis. Its tetralone core is found in bioactive natural products and pharmaceutical agents targeting the central nervous system and other therapeutic areas; the 8-hydroxy substitution pattern introduces additional opportunities for pharmacophore elaboration through metal coordination or hydrogen-bond donor interactions with biological targets.
Beyond medicinal chemistry, 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one is employed as a chiral-auxiliary precursor and as a substrate for asymmetric reduction studies, where the prochiral ketone is reduced to the corresponding β-hydroxy tetralone with defined stereochemistry using chiral catalysts or biocatalytic systems. Its well-defined structure also makes it a useful reference standard and analytical calibrant in HPLC method development for structurally related compounds.
Handling, Storage, and Safety Considerations
As with most phenolic ketone reagents, 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one should be handled with standard laboratory precautions. Personnel are advised to wear appropriate personal protective equipment, including gloves, safety glasses, and a laboratory coat, to minimize dermal and ocular exposure to the solid or any solutions thereof.
The compound should be stored in a tightly sealed container in a cool, dry location, away from strong oxidizing agents and direct light, to preserve its chemical integrity. While specific GHS hazard classifications for this compound should be confirmed from the current Safety Data Sheet (SDS) supplied by Aladdin Scientific, researchers should treat all fine organic solids as potential respiratory irritants and work in a well-ventilated area or fume hood when weighing or dissolving the material.
Frequently asked questions
What is the molecular formula and molecular weight of 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one?
The molecular formula of 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one is C₁₀H₁₀O₂ and its molecular weight is approximately 162.19 g/mol. These values reflect the bicyclic tetralone scaffold bearing one hydroxyl and one ketone oxygen.
How should 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one be stored to maintain stability?
The compound should be stored in a tightly sealed container in a cool, dry place away from direct light and strong oxidizing agents. Consulting the current SDS supplied with the product is recommended for detailed storage and stability information.
What are the primary research uses of 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one?
This compound is widely used as a bifunctional synthetic intermediate for constructing polycyclic and heterocyclic frameworks in medicinal chemistry, as a substrate in asymmetric reduction studies, and as a reference standard in analytical method development. Its dual phenolic hydroxyl and ketone functionalities enable orthogonal chemical transformations.
What is the Aladdin Scientific product SKU for 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one?
3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one is available from Aladdin Scientific under SKU D698198.
References
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 4th ed.; Wiley-Interscience: New York, 1992. (General reference for Friedel–Crafts acylation and tetralone synthesis)
- Clayden, J.; Greeves, N.; Warren, S. Organic Chemistry, 2nd ed.; Oxford University Press: Oxford, 2012. (Textbook reference for phenolic ketone reactivity and functional-group transformations)
- Aladdin Scientific. Product Page: 3,4-Dihydro-8-hydroxynaphthalen-1(2H)-one, SKU D698198. (Supplier product information)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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