Naphthalene-1,5-diyl diacetate is a symmetrical aromatic diester derived from 1,5-naphthalenediol and acetic anhydride, valued in organic synthesis as a protected diol building block and as a reference compound in chemical research.
- Chemical Name
- Naphthalene-1,5-diyl diacetate
- SKU
- N694249
- Chemical Class
- Aromatic diester (diacetate of 1,5-naphthalenediol)
- Parent Diol
- 1,5-Naphthalenediol (naphthalene-1,5-diol)
- Symmetry
- Symmetric molecule; both hydroxyl groups of 1,5-naphthalenediol are acetylated
- Typical Use
- Protected diol building block in organic synthesis; reference standard
What Is Naphthalene-1,5-diyl Diacetate?
Naphthalene-1,5-diyl diacetate is the diacetate ester of 1,5-naphthalenediol, a polycyclic aromatic compound in which both phenolic hydroxyl groups at the 1- and 5-positions of the naphthalene ring system are protected as acetate esters. This symmetric substitution pattern imparts defined physicochemical properties and makes the compound a useful intermediate or reference material in synthetic organic chemistry.
The compound is catalogued under SKU N694249 at Aladdin Scientific and is intended for research and laboratory use.
Key Physical and Chemical Properties
As an aromatic diester, Naphthalene-1,5-diyl diacetate is expected to be a solid at room temperature with moderate lipophilicity. Key property considerations include:
- Solubility: Likely soluble in common organic solvents such as dichloromethane, ethyl acetate, acetone, and dimethyl sulfoxide (DMSO); sparingly soluble or insoluble in water, consistent with the nonpolar aromatic diester character.
- Stability: Acetate esters on aromatic rings are susceptible to hydrolysis under strongly acidic or basic aqueous conditions, regenerating 1,5-naphthalenediol. Under neutral, dry conditions the compound is expected to be stable.
- Reactivity: The ester groups can be cleaved by hydrolysis (acid or base catalysis) or by transesterification, providing a route back to the free diol.
Note: Specific numerical values for melting point, boiling point, and logP are not confirmed in the available source material and should be verified against the product Certificate of Analysis (CoA) or a validated chemical database.
Handling, Storage, and Safety Guidelines
When working with Naphthalene-1,5-diyl diacetate in a research setting, observe standard laboratory safety practices for aromatic organic compounds:
- Personal Protective Equipment (PPE): Wear appropriate gloves (nitrile recommended), safety glasses, and a lab coat. Use in a well-ventilated area or fume hood.
- Storage: Store in a tightly sealed container in a cool, dry place away from moisture, heat, and incompatible materials (strong bases, strong acids, oxidizing agents). Specific temperature recommendations should be confirmed on the product label or CoA.
- Disposal: Dispose of according to local institutional and governmental regulations for organic chemical waste.
- SDS: Always consult the Safety Data Sheet (SDS) supplied with SKU N694249 before use for complete hazard information.
Applications in Research and Synthesis
Naphthalene-1,5-diyl diacetate finds utility in several areas of chemical research:
- Protected Diol Intermediate: The acetate groups serve as protecting groups for the 1,5-naphthalenediol hydroxyls, allowing selective chemistry to be performed elsewhere on a molecule before deprotection.
- Reference Standard: The compound can serve as an analytical reference standard for method development and validation in HPLC or other chromatographic techniques.
- Supramolecular and Materials Chemistry: Naphthalene-based building blocks are widely used in the construction of host-guest systems, fluorescent materials, and porous organic frameworks due to the planar aromatic core.
- Precursor Chemistry: Hydrolysis or transesterification of the diacetate provides access to 1,5-naphthalenediol, which is itself a versatile building block for dyes, polymers, and ligands.
Specific literature references for each application should be verified independently, as detailed citations are not available in the current source material.
Ordering and Product Information
Naphthalene-1,5-diyl diacetate is available from Aladdin Scientific under the following details:
- SKU: N694249
- Product Name: Naphthalene-1,5-diyl diacetate
- Intended Use: Research use only (RUO)
For pricing, availability, pack sizes, and current stock status, please visit the Aladdin Scientific website or contact our customer service team. Bulk quantities and custom packaging may be available upon request. A Certificate of Analysis (CoA) and Safety Data Sheet (SDS) are available for download on the product page or upon request.
Frequently asked questions
What is the chemical structure of Naphthalene-1,5-diyl diacetate?
Naphthalene-1,5-diyl diacetate consists of a naphthalene ring system with acetate ester groups (-OC(O)CH₃) at the 1- and 5-positions, replacing the hydroxyl groups of the parent compound 1,5-naphthalenediol. The molecule is symmetric due to the identical substitution at both positions.
How should Naphthalene-1,5-diyl diacetate be stored to maintain its integrity?
The compound should be stored in a tightly sealed container in a cool, dry environment, protected from moisture, heat, and incompatible reagents such as strong acids and bases that could promote hydrolysis of the acetate ester groups. Always refer to the product label and SDS for confirmed storage conditions specific to SKU N694249.
Can Naphthalene-1,5-diyl diacetate be hydrolyzed back to 1,5-naphthalenediol?
Yes. As with other aromatic acetate esters, the acetate protecting groups can be cleaved under acidic or basic aqueous conditions to regenerate 1,5-naphthalenediol. Mild base hydrolysis (e.g., potassium carbonate in methanol) is a common laboratory approach for removing acetate protecting groups from phenols.
What solvents are recommended for dissolving Naphthalene-1,5-diyl diacetate?
Based on the lipophilic aromatic diester character of the compound, organic solvents such as dichloromethane, ethyl acetate, acetone, chloroform, or DMSO are expected to provide good solubility. Aqueous solubility is expected to be low. Solubility should be experimentally verified before use in a specific application.
Is Naphthalene-1,5-diyl diacetate suitable for use as an analytical reference standard?
The compound may be used as a reference standard for analytical method development and validation, for example in HPLC purity assays. For use as a certified reference standard, please confirm the purity grade and consult the Certificate of Analysis (CoA) for SKU N694249 available from Aladdin Scientific.
References
- Aladdin Scientific Product Page: Naphthalene-1,5-diyl diacetate, SKU N694249.
- March, J. Advanced Organic Chemistry: Reactions, Mechanisms, and Structure. Wiley-Interscience. (General reference for ester hydrolysis and protecting group chemistry.)
- Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis. Wiley. (Reference for acetate protecting group chemistry on phenols.)
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.