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Description
2-Ethynyl-6-methoxynaphthalene is a polycyclic aromatic compound carrying a terminal alkyne group at the two position and a methoxy group at the six position of the naphthalene framework. This combination makes it a highly sought-after non-heterocyclic building block in the synthesis of conjugated molecules. The terminal ethynyl group serves as an exceptionally versatile reaction handle, particularly for palladium- and copper-catalysed cross-coupling, while the methoxylated naphthalene core supplies a rigid, electron-rich aromatic scaffold with fluorescent character. In the laboratory, this compound acts as a starting point toward organic electronic materials as well as pharmaceutical intermediates.
The characteristic that makes it a preferred choice is the selective reactivity of the terminal alkyne group. The acetylenic hydrogen can be deprotonated to form metal acetylides, while the triple bond participates in Sonogashira coupling, azide–alkyne click reactions, hydrosilylation, and cycloadditions that construct new rings. The methoxy group at the six position donates electron density into the aromatic system, shifting the absorption and emission behaviour of the naphthalene framework while also directing subsequent aromatic substitution reactions. The rigidity of the naphthalene core further supports predictable geometry in the products assembled from it.
In Indonesian laboratories, this building block is typically drawn upon by university and institutional research groups working on organic synthesis, materials chemistry, and medicinal chemistry programmes. It is handled in small quantities on the bench for exploratory coupling reactions, then carried forward once conditions are established. Because it is supplied as a TCI catalogue item under the code E1627, it is generally ordered on a per-project basis alongside the catalysts, ligands, and solvents required for the coupling chemistry it enables.
Laboratory Applications
- Sonogashira cross-coupling: the terminal alkyne pairs directly with aryl and vinyl halides under palladium and copper catalysis, extending conjugation from the methoxynaphthalene core in a single step.
- Azide–alkyne click chemistry: the acetylenic triple bond reacts with organic azides to install triazole linkages, letting researchers append the fluorescent naphthalene unit onto larger molecular architectures.
- Organic electronic materials research: the rigid, electron-rich methoxynaphthalene scaffold serves as a donor fragment when building conjugated systems whose absorption and emission behaviour is being tuned deliberately.
- Pharmaceutical intermediate synthesis: the compound functions as an advanced starting material in medicinal chemistry routes where a substituted naphthalene framework must be elaborated through alkyne-based transformations.
- Metal acetylide preparation: deprotonation of the acetylenic hydrogen generates nucleophilic acetylide species useful for carbon–carbon bond formation with electrophiles in multi-step synthetic sequences.
Specifications
- Brand: TCI (Tokyo Chemical Industry), catalogue code E1627
- CAS number: 129113-00-4
- Chemical name: 2-Ethynyl-6-methoxynaphthalene
- Category: Chemistry > Building Blocks > Non-Heterocyclic Building Blocks
- Pack sizes: available in standard TCI research-scale packaging; please confirm the size required when ordering
- Storage: keep in the tightly closed original container under the conditions stated on the manufacturer's label and safety data sheet
Handling and Storage
Store the container tightly closed in a cool, dry, well-ventilated area away from direct sunlight, heat sources, and ignition sources, following the specific conditions printed on the TCI label and safety data sheet. Keep the material in its original supplier container, or in a compatible tightly sealed glass vessel, and protect it from moisture and prolonged air exposure. Handle it inside a fume hood while wearing safety goggles, chemical-resistant gloves, and a laboratory coat. Avoid inhalation of dust or vapour and avoid contact with skin and eyes. Segregate it from strong oxidising agents and strong bases during storage. Weigh and transfer only the quantity needed, reseal the container promptly, and dispose of residues and contaminated materials through the institution's chemical waste procedures. Consult the manufacturer's safety data sheet before first use.
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