1,5-Diisocyanonaphthalene

Chemical compound 1,5-DIN.svg 125px Structural formula of 1,5-diisocyanonaphthalene 1,5-Diisocyanonaphthalene DIN; 1,5-naphthalenediyldiisocyanide 944-69-4 changed CAS 32917437 55274462 1S/C12H6N2/c1-13-11-7-3-6-10-9(11)5-4-8-12(10)14-2/h3-8H HOWLRJRIWHGYOH-UHFFFAOYSA-N [C-]#[N+]C1=CC=CC2=C1C=CC=C2[N+]#[C-] 12 6 2 Solid Laboratory chemical; handle with standard precautions 1,5-Diisocyanonaphthalene (DIN) is an aromatic diisocyanide (isonitrile) in which two –N≡C groups occupy the 1- and 5-positions of the naphthalene ring. The compound is also named 1,5-naphthalenediyldiisocyanide and has the molecular formula C12H6N2 and relative molar mass 178.19 g/mol.1,5-Naphthalenediyldiisocyanide https://pubchem.ncbi.nlm.nih.gov/compound/55274462 pubchem.ncbi.nlm.nih.gov 19 August 2025 en It has been studied as a photophysical probe and as a lead compound for antifungal research. Structure and properties Isocyanides feature the –N≡C functional group (often depicted as –N+≡C− ↔ –N=C:), bonded to the aromatic ring through nitrogen. DIN's two isocyanide substituents make it a rigid, weakly polar π-system. Photophysically, DIN shows limited solvatochromism compared with mono-formamido/mono-isocyano analogues (e.g., ICNF), but it forms notable π-complexes with aromatic solvents that modulate emission, enabling discrimination among aromatics by fluorescence.Kopcsik Erika Mucsi Zoltán Schiwert Rajmond Vanyorek László Viskolcz Béla Nagy Miklós Aromatic pi-complexation of 1,5-diisocyanonaphthalene with benzene derivatives Scientific Reports 2025-01-03 15 1 629 10.1038/s41598-024-84769-3 39753877 11698713 2025NatSR..15..629K free Synthesis 1,5-Diisocyanonaphthalene can be obtained by converting 1,5-diaminonaphthalene to the corresponding N,N-diformamide, followed by dehydration (e.g., with phosphorus oxychloride in the presence of base). Reaction conditions and solvent choice influence outcome for this system. Kopcsik Erika Mucsi Zoltán Kontra Bence Vanyorek László Váradi Csaba Viskolcz Béla Nagy Miklós Preparation and Optical Study of 1-Formamido-5-Isocyanonaphthalene, the Hydrolysis Product of the Potent Antifungal 1,5-Diisocyanonaphthalene International Journal of Molecular Sciences 2023 24 9 7780 10.3390/ijms24097780 37175485 10177923 free Applications Fluorescence/analytical: DIN's emission responds to specific π–π interactions in aromatic solvents, suggesting use in distinguishing aromatic hydrocarbons optically; related hydrolysis-derived ICNF is a strongly solvatochromic dye. Antifungal activity In standardized CLSI broth microdilution tests against three Aspergillus fumigatus strains (MYA 3627, ATCC 204305 and Af293), 1,5-diisocyanonaphthalene showed the lowest MIC values among the tested isocyano-naphthalene derivatives, namely 0.6 μg/mL (3.4 μM) for all strains. Practical use may be limited by poor aqueous solubility; a related dimethylamino analogue (DIMICAN) progressed to in-vivo evaluation in a murine aspergillosis model.Szigeti Zsuzsa Máthéné Tálas László Széles Adrienn Hargitai Zoltán Nagy Zsolt László Nagy Miklós Kiss Alexandra Kéki Sándor Szemán-Nagy Gábor Potential Original Drug for Aspergillosis: In Vitro and In Vivo Effects of 1-N,N-Dimethylamino-5-Isocyanonaphthalene (DIMICAN) on Aspergillus fumigatus Journal of Fungi 2022 8 10 985 10.3390/jof8100985 36294550 9605569 free See also Isocyanide Naphthalene References Category:Isocyanides Category:Naphthalenes Category:Antifungals