66217-26-3

Usage

Derivative of

Naphthalene

Common uses

Synthesis of pharmaceuticals and agrochemicals

Physical properties

Color: Colorless to yellow
Odor: Strong aromatic
Solubility: Insoluble in water, soluble in most organic solvents

Hazards

Can cause irritation to skin, eyes, and respiratory system upon exposure
Should be handled with care

Upstream product

• 66217-19-4 2-ethoxy-6-bromo-naphthalene 
• 544-92-3 copper(I) cyanide 
• 74-96-4 ethyl bromide 
• 52927-22-7 6-cyano-2-naphthol 
• 15231-91-1 6-bromo-naphthalen-2-ol 

Relevant academic research and scientific papers

Discovery of a sensitive, selective, and tightly binding fluorogenic substrate of bovine plasma amine oxidase

(Chemical Equation Presented) We report a novel fluorogenic substrate of bovine plasma amine oxidase (BPAO), namely, (2-(6-(aminomethyl)naphthalen-2- yloxy)ethyl)trimethylammonium (ANETA), which displays extremely tight binding to BPAO (Km 183 ± 14 nM) and yet is metabolized fairly quickly (kcat 0.690 ± 0.010 s-1), with the aldehyde turnover product (2-(6-formylnaphthalen-2-yloxy)ethyl)trimefhylammonium serving as a real time reporting fluorophore of the enzyme activity. This allowed for the development of a fluorometric noncoupled assay that is 2 orders of magnitude more sensitive than the spectrophotometric benzylamine assay. The discovery of ANETA involved elaboration of the lead compound 6-methoxy-2-naphthalene- methaneamine by structure-based design, which recognized the ancillary cation binding site of BPAO as the most significant structural features controlling binding affinity. Structure-based design further ensured a high level of selectivity: ANETA is a good substrate of BPAO but is not a substrate of either porcine kidney diamine oxidase (pkDAO) or rat liver monoamine oxidase (MAO-B). ANETA represents the first highly sensitive, selective, and tight binding fluorogenic substrate of a copper amine oxidase that is able to respond directly to the enzyme activity in real time.

Naphthyl organic compounds

Liquid crystal compounds of formula (I) are described, where formula (I) is given as R1 --A--(Xm --(B)n --R2 where A is selected from nathyl, flourinated naphthyl, brominated naphthyl, B is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R1 and R2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, X is selected from C C, COO and C C, m is 0 or 1, n is 0 or 1 where m is 1 and n is 0 where m is 0; provided that where A is naphthyl, n is 1 and m is 0 then B is selected from methylated phenyl, brominated phenyl, thiophene, pyrimidine and pyridine; and further provided that where A is naphthyl, X is C C, m is 1 and n is 1, then B is selected from thiophene, pyrimidine and pyridine. Also described are liquid crystal compounds suitable for inclusion in devices utilizing pretransitional characteristics of liquid crystalline materials in the isotropic phase and described by formula (II): R3 --J--(Y)p --(Z)q --R 4, where J is selected from nathyl, fluorinated naphthyl, brominated naphthyl, Z is selected from phenyl, methylated phenyl, brominated phenyl, fluorinated phenyl, thiophene, pyrimidine and pyridine, R1 and R2 are independently selected from alkyl, alkoxy, alkynyl, thioalkyl, Br, CN, SCN, NCS, perfluoroalkyl, perfluoroalkoxy and hydrogen, Y is selected from C=C, COO and C=C, p is 0 or 1, q is 0 or 1 where p is 1 and q is 0 where p is 0.