142167-39-3

Basic information

• Product Name: Methanone, (5-bromo-4-chloro-2-hydroxyphenyl)-2-pyridinyl-
• CAS NO: 142167-39-3
• Molecular Formula: C12H7BrClNO2
• Molecular Weight: 312.55
• Mol File: 142167-39-3.mol

Chemical Properties

• CAS DataBase Reference: Methanone, (5-bromo-4-chloro-2-hydroxyphenyl)-2-pyridinyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (5-bromo-4-chloro-2-hydroxyphenyl)-2-pyridinyl-(142167-39-3)
• EPA Substance Registry System: Methanone, (5-bromo-4-chloro-2-hydroxyphenyl)-2-pyridinyl-(142167-39-3)

Safety Data

• Hazardous Substances Data: 142167-39-3(Hazardous Substances Data)

Upstream product

• 5106-98-9 4-chlorosalicylic acid 
• 109-04-6 2-bromo-pyridine 
• 142167-38-2 5-bromo-4-chloro-2-hydroxybenzoic acid 

Downstream Products

• 157302-01-7 4-bromo-5-chloro-2-(imino-pyridin-2-yl-methyl)-phenol 

Relevant articles and documents

Process development of potassium channel opener, TCV-295, based on convenient ring formation of 2H-1,3-benzoxazine and selective N-oxidation of the pyridyl moiety

An efficient process for potassium channel opener, TCV-295, based on a novel and convenient 4-(2-pyridyl)-2H-1,3-benzoxazine ring formation from o-hydroxybenzoylpyridine by the NH4I/piperidine/2,2-dimethoxypropane system and the following selective pyridine-N-oxidation using dimethyldioxirane, has been developed. Additionally, the combination reagent of ammonium halide and sec- or tert- amine conveniently converted o-hydroxyphenyl arylketones with several ketones (or benzaldehyde) to various novel 4-aryl-2H-1,3-benzoxazines.

Synthesis and biological activity of novel 1,3-benzoxazine derivatives as K+ channel openers

A new series of 1,3-benzoxazine derivatives with a 2-pyridine 1-oxide group at C4 was designed to explore novel K+ channel openers. Synthesis was carried out by using a palladium(0)-catalyzed carbon-carbon bond formation reaction of imino-triflates with organozinc reagents and via a new one-pot 1,3-benzoxazine skeleton formation reaction of benzoylpyridines. The compounds were tested for vasorelaxant activity in tetraethylammonium chloride (TEA) and BaCl2-induced and high KCl-induced contraction of rat aorta to identify potential K+ channel openers, and also for oral hypotensive effects in spontaneously hypertensive rats. An electron- withdrawing group with the proper shape at C6 and a methyl or halogens group at C7 of the 1,3-benzoxazine nucleus were required for the development of optimal vasorelaxant and hypotensive activity. In particular, 2-(6-bromo-7- chloro-2,2-dimethyl-2H-1,3-benzoxazin-4-yl)pyridine 1-oxide (71) showed more potent vasorelaxant activity (EC50=0.14 μM) against TEA and BaCL2- induced contraction and longer-lasting hypotensive effects than cromakalim (1).

1,3-benzoxazine derivatives, their production and use

A new compound of the formula: STR1 wherein STR2 is an optionally substituted benzene ring; R1 is a carbocyclic or heterocyclic group which is linked to the 4-position of the 1,3-benzoxazine ring through a carbon-carbon bond, a hydrocarbon resi