The Chemistry of 1,8-Diaminonaphthalene: Properties and Synthesis
Understanding the fundamental chemistry of a compound is essential for anyone involved in its use, from research scientists to procurement managers. 1,8-Diaminonaphthalene (CAS 479-27-6) is a fascinating organic molecule with a unique structure and reactivity profile that makes it a valuable intermediate. As a manufacturer and supplier, we believe in providing our clients with this foundational knowledge to support their applications.
1,8-Diaminonaphthalene, with the molecular formula C10H10N2, features a naphthalene core substituted with two amino (-NH2) groups at the peri positions (1 and 8). This specific arrangement of amino groups influences its chemical behavior significantly. The molecule's structure lends itself to forming chelate complexes with metal ions and participating in cyclization reactions, forming various heterocyclic systems.
In terms of physical properties, 1,8-Diaminonaphthalene typically presents as needle crystals, with a melting point in the range of 60-65 °C. It exhibits solubility in common organic solvents like ethanol and ether, while its solubility in water is limited. The compound can be sensitive to air and light, tending to darken over time, which is why proper storage conditions, as advised by suppliers, are crucial for maintaining its quality.
The synthesis of 1,8-Diaminonaphthalene commonly involves the reduction of 1,8-dinitronaphthalene. This reduction can be achieved through various methods, including chemical reduction using agents like iron in acetic acid, or catalytic hydrogenation. The choice of synthesis route can influence the final purity and cost of the product. Manufacturers often optimize these processes to ensure high yields and purity, making the compound accessible for buyers who need to purchase it for their industrial needs.
The reactivity of the amino groups allows 1,8-Diaminonaphthalene to act as a nucleophile and a base. It undergoes electrophilic aromatic substitution, typically at the 4-position of the naphthalene ring. Furthermore, its ability to couple with diazonium salts makes it a precursor for azo dyes. For those looking to buy this intermediate, understanding these chemical aspects helps in predicting its behavior in various reactions and applications, ensuring efficient use and optimal results.
Perspectives & Insights
Logic Thinker AI
“The synthesis of 1,8-Diaminonaphthalene commonly involves the reduction of 1,8-dinitronaphthalene.”
Molecule Spark 2025
“This reduction can be achieved through various methods, including chemical reduction using agents like iron in acetic acid, or catalytic hydrogenation.”
Alpha Pioneer 01
“The choice of synthesis route can influence the final purity and cost of the product.”