A fluorinated o-aminobenzonitrile

Used as a synthetic precursor for heterocycles in the applications of APIs and ligands

| |

2-Amino-5-fluorobenzonitrile (CAS number 61272-77-3) possesses multiple functional groups, including an amine, a nitrile and a fluoride. The ortho-positioning of the amine and nitrile substituents makes 2-amino-5-fluorobenzonitrile an ideal precursor for synthesising heterocyclic compounds. 2-Amino-5-fluorobenzonitrile reacts with aminoethanol derivatives catalysed by zinc chloride, yielding oxazoline ligands for use in Cu-catalysed enantioselective nitroaldol reactions. Through its reaction with cyclic ketone in Friedländer reaction, 2-amino-5-fluorobenzonitrile serves as a precursor for tacrine derivatives. In the case of synthesising quinazoline/quinazolinone derivatives, the reaction of 2-amino-5-fluorobenzonitrile with cyclic ketones derivatives occurs under basic condition.

General Information

Chemical Structure

Product Details

MSDS Documentation

Literature and Reviews

1. Structure-activity relationships of dually-acting acetylcholinesterase inhibitors derived from tacrine on N-methyl-D-Aspartate receptors, L. Gorecki et al., Eur. J. Med. Chem., 219, 113434(2021); DOI: 10.1016/j.ejmech.2021.113434.
2. Cobalt-catalyzed tandem transformation of 2-aminobenzonitriles to quinazolinones using hydration and dehydrogenative coupling strategy, A. Samin et al., J. Org. Chem., 85, 11359–11367(2020); DOI: 10.1021/acs.joc.0c01307.
3. Chiral pyridine oxazoline and 1,2,4‑triazine oxazoline ligands incorporating electron‑withdrawing substituents and their application in the Cu‑catalyzed enantioselective nitroaldol reaction, E. Wolińska et al., Monatsh. Chem., 153, 245–256(2022); DOI: 10.1007/s00706-022-02893-0.