A NOVEL ELECTROPHILIC REAGENT, 4-(N-CHLOROFORMYLMETHYL-N-METHYL) -7-N,N-DIMETHYLAMINOSULPHONYL-2,1,3-BENZOXADIAZOLE (DBD-COCL) FOR FLUOROMETRIC DETECTION OF ALCOHOLS, PHENOLS, AMINES AND THIOLS

A novel electrophilic reagent for alcohols, phenols, amines and thiols , 4-(N-chloroformylmethyl-N-methyl)amino-7-N dimethylaminosulphonyl-2, 1,3-benzoxadiazole (DBD-COCl) was synthesized. The reactivity of the r eagent to these nucleophiles was studied using high-performance liquid chromatography (HPLC) with precolumn derivatization techniques. DBD-C OCL reacted in benzene solution at the room temperature or 60-degrees- C with androsterone (a representative of hydroxyls), (-)-mandelic and D,L-lactic acid (hydroxy acid), estrone (phenol), benzylamine (primary amine), phenetidine (aromatic amine) and alpha-mercapto-N,2-naphthyla cetamide (thiol) to give fluorescent products bearing fluorescence wav elengths at between 543 nm and 555 nm (excitation at between 437 nm an d 445 nm). The base catalyst, quinuclidine was required to complete th e reaction with the nucleophiles except aromatic amines. The reaction solution was subjected to a reversed phase HPLC and the detection limi ts of the derivatives were at the femto mol range on column.