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Description
TCI D3519 2,6-Dimethoxynaphthalene is an aromatic building block consisting of a naphthalene core bearing two methoxy groups symmetrically placed at the 2 and 6 positions. As an electron-rich polycyclic aromatic compound, this material occupies a distinct role in organic synthesis and materials chemistry laboratories. The naphthalene framework provides a rigid, extended aromatic plane capable of interacting through pi-stacking, while the two methoxy groups modulate the electron density of the rings and direct aromatic substitution reactions toward specific positions, making the synthesis of its derivatives easier to control than that of unsubstituted naphthalene.
The characteristics that make this compound a frequent choice are the electron-donating nature of its methoxy groups and the symmetry of its structure. The electron-rich rings are highly responsive to electrophilic substitution reactions such as Friedel-Crafts acylation, halogenation, and formylation, which typically proceed at the 1 or 5 positions with clear regiochemical direction. The symmetry of the 2 and 6 positions simplifies nuclear magnetic resonance spectra and makes reaction monitoring more straightforward. As a crystalline solid, the compound is stable, easy to weigh accurately, and can be purified by recrystallization.
In Indonesian laboratories, this building block is typically used in university and institutional research groups working on organic synthesis, in materials chemistry programs exploring functional aromatic systems, and in industrial research units developing specialty intermediates. It is generally handled at the bench scale, where its crystalline form and predictable substitution behaviour suit multi-step synthetic routes, method development work, and the preparation of reference derivatives for analytical comparison.
Laboratory Applications
- Friedel-Crafts acylation studies: the electron-rich naphthalene rings react readily with acylating agents, and the clear positional direction gives predictable, easily identified products.
- Halogenation and functionalisation routes: substitution proceeds with defined regiochemistry, allowing halogenated intermediates to be prepared as reliable starting points for coupling chemistry.
- Formylation for aldehyde intermediates: the activated aromatic system supports formylation reactions that install a carbonyl handle for subsequent condensation or reduction steps.
- Materials chemistry and pi-stacking research: the rigid, extended aromatic plane makes it useful for building functional aromatic systems where intermolecular stacking interactions matter.
- Synthetic method development and teaching: the symmetric substitution pattern simplifies nuclear magnetic resonance interpretation, so reaction progress and product identity can be confirmed quickly.
Specifications
- Brand: TCI
- CAS number: 5486-55-5
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI catalogue pack sizes; please confirm the size required when ordering
- Physical form: crystalline solid
- Storage: store in a closed container under normal recommended conditions for organic crystalline reagents
Handling and Storage
Store the material in a tightly closed original container, kept in a cool, dry, and well ventilated area away from heat sources, direct sunlight, and incompatible chemicals such as strong oxidising agents. Glass containers with secure closures are suitable, and the container should be resealed promptly after each use to limit moisture uptake and dust generation. Handle the solid in a fume hood or a well ventilated weighing area, and wear a laboratory coat, safety glasses, and chemically resistant gloves. Avoid inhaling dust and avoid contact with skin and eyes. Weigh with clean, dry spatulas to prevent cross contamination, keep containers clearly labelled, and consult the manufacturer's safety data sheet before use and for disposal guidance.
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