1-Isocyano-5-aminonaphthalene

1-Isocyano-5-aminonaphthalene
Names
	Preferred IUPAC name 5-Isocyanonaphthalen-1-amine
	Other names 5-Amino-1-isocyanonaphthalene; ICAN
Identifiers
CAS Number	1620067-61-9 ;
3D model (JSmol)	Interactive image;
ChemSpider	61012044;
PubChem CID	102102046;
	InChI InChI=1S/C11H8N2/c1-13-11-7-3-4-8-9(11)5-2-6-10(8)12/h2-7H,12H2 Key: ZGMMMIZCNKPHTB-UHFFFAOYSA-N;
	SMILES [C-]#[N+]c1cccc2c1cccc(N)2;
Properties
Chemical formula	C11H8N2
Molar mass	168.199 g·mol−1
Appearance	Yellow–orange solid (reported)
Solubility in water	Low in water; soluble in organic solvents
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

1-Isocyano-5-aminonaphthalene (commonly ICAN) is a substituted naphthalene bearing an isocyano (–N≡C) group and an amino (–NH₂) group in a 1,5-relationship. The push–pull pairing of an electron donor (amino) and an electron-withdrawing (isocyano) group gives ICAN a pronounced intramolecular charge-transfer (ICT) character, which underlies its strong solvatochromic fluorescence and its use as an environment-sensitive fluorophore. ICAN and several N-alkylated analogues have also been explored as antifungal leads, with reports of low minimum inhibitory concentrations (MICs) against Candida spp. and proof-of-concept efficacy of a dimethylated derivative in a neutropenic mouse model.