1,7-DIAZA-12-CROWN-4

white to slightly yellow needle like

1,7-Diaza-12-crown-4 can be used to prepare:

• A ligand named N,N′-bis[(6-carboxy-2-pyridyl)methyl]-1,7-diaza-12-crown-4, which is used to synthesize lanthanide metal complexes applicable as MRI contrast agents.
• A novel chiral receptor that can be used in the separation of enantiomers using capillary electrophoresis.
• A fluorescent anthracene based diazacrown ether, which can be used as a photoinduced electron transfer (PET) fluorescent sensor for guest cations.

Preparation of azacrown ether: the bromine salt of compound 1,7-dioxa-4,10-tetraaza (2.6 g, 5.39 mmol) and phenol (3.04 g, 32.32 mmol) were added to 150 mL of 33% hydrogen bromide acetic acid solution. The reaction was warmed up to reflux at 80 C and stirred for 60 h. After the reaction was cooled down, the reaction solution was directly evaporated to 15 mL under reduced pressure, to which 120 mL of acetone was added, and a large amount of gray solid was precipitated immediately, and then filtered under reduced pressure, washed with acetone (330 mL), and dried in vacuum to obtain 1.1 g of the gray solid compound which was the azacrown ether.