152684-30-5

Basic information

• Product Name: 5-BROMO-2-METHOXY-3-NITRO-PYRIDINE
• Synonyms: 5-BROMO-2-METHOXY-3-NITRO-PYRIDINE;2-METHOXY-3-NITRO-5-BROMOPYRIDINE;5-BroMo-2-Methoxy-3-nitropyridine, 97+%;Pyridine,5-bromo-2-methoxy-3-nitro-
• CAS NO: 152684-30-5
• Molecular Formula: C₆H₅BrN₂O₃
• Molecular Weight: 233.02
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Boronic Acid;Pyridine Series;Heterocycle-Pyridine series
• Mol File: 152684-30-5.mol
• Article Data: 29

Chemical Properties

• Melting Point: 88.0 to 92.0 °C
• Boiling Point: 281.982 °C at 760 mmHg
• Flash Point: 124.339 °C
• Appearance: Light yellow liquid
• Density: 1.73 g/cm³
• Vapor Pressure: 0.006mmHg at 25°C
• Refractive Index: 1.587
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: -2.99±0.20(Predicted)
• CAS DataBase Reference: 5-BROMO-2-METHOXY-3-NITRO-PYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-BROMO-2-METHOXY-3-NITRO-PYRIDINE(152684-30-5)
• EPA Substance Registry System: 5-BROMO-2-METHOXY-3-NITRO-PYRIDINE(152684-30-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 152684-30-5(Hazardous Substances Data)

Usage

Description

5-Bromo-2-methoxy-3-nitro-pyridine is a chemical compound characterized by a pyridine ring with a bromine atom, a methoxy group, and a nitro group as substituents. It serves as a versatile intermediate in the synthesis of various pharmaceuticals and agrochemicals, and is recognized for its potential in developing drugs for a range of therapeutic applications.

Uses

Used in Pharmaceutical Industry:
5-Bromo-2-methoxy-3-nitro-pyridine is used as a key intermediate in the synthesis of pharmaceutical compounds for its ability to contribute to the development of drugs with anti-inflammatory, antimicrobial, and antiparasitic properties. Its unique structure allows for the creation of novel therapeutic agents that can address specific medical needs.
Used in Agrochemical Industry:
In the agrochemical sector, 5-Bromo-2-methoxy-3-nitro-pyridine is utilized as an intermediate in the production of agrochemicals, potentially enhancing crop protection and management through the development of new pesticides or herbicides.
Used in Organic Material Synthesis:
5-Bromo-2-methoxy-3-nitro-pyridine is also used as a building block in the synthesis of organic materials, contributing to the advancement of material science by providing a structurally diverse component for the creation of new compounds with specific properties.
Used in Chemical Research:
As a chemical compound with notable reactivity and potential, 5-Bromo-2-methoxy-3-nitro-pyridine is used in research settings to explore its properties and reactions, furthering the understanding of chemical behavior and facilitating the discovery of new chemical entities.

InChI:InChI=1/C6H5BrN2O3/c1-12-6-5(9(10)11)2-4(7)3-8-6/h2-3H,1H3

Upstream product

• 67443-38-3 5-bromo-2-chloro-3-nitropyridine 
• 124-41-4 sodium methylate 
• 6945-68-2 5-bromo-3-nitro-pyridin-2-ylamine 
• 1072-97-5 5-bromo-2-pyridylamine 
• 67-56-1 methanol 
• 15862-34-7 5-bromo-3-nitro-2-pyridone 
• 74-88-4 methyl iodide 
• 13472-85-0 2-methoxy-5-bromopyridine 

Downstream Products

• 152684-22-5 2-methoxy-5-(4-methylphenyl)-3-nitropyridine 
• 1086062-66-9 GS⁽²⁶⁴⁾K₂₁₅₈ 
• 1086063-46-8 N-(5-bromo-2-methoxypyridine-3-yl)-2,4-difluorobenzene sulfonyl chloride 
• 1360537-69-4 N-(5-bromo-2-methoxypyridin-3-yl)-4-fluoro-2-nitrobenzenesulfonamide 
• 1360537-71-8 4-fluoro-N-(2-methoxy-5-(4-(pyridazin-4-yl)quinolin-6-yl)pyridin-3-yl)-2-nitrobenzenesulfonamide 
• 1360537-72-9 2-fluoro-N-(2-methoxy-5-(4-(pyridazin-4-yl)quinolin-6-yl)pyridin-3-yl)-4-nitrobenzenesulfonamide 
• 1360537-73-0 2,4-difluoro-N-(2-hydroxy-5-(4-(pyridazin-4-yl)quinolin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 1360537-75-2 2-[⁽¹⁸⁾F]fluoro-4-fluoro-N-(2-methoxy-5-(4-(pyridazin-4-yl)quinolin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 1551453-19-0 2,4-difluoro-N-(5-(4-(3-hydroxyprop-1-yn-1-yl)quinolin-6-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 
• 1551454-59-1 2,4-difluoro-N-(2-methoxy-5-(4-((trimethylsilyl)ethynyl)quinolin-6-yl)pyridin-3-yl)benzenesulfonamide 
• 1551453-47-4 N-(5-(4-ethynylquinolin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 
• 1551453-50-9 N-(5-(4-((1H-pyrazol-4-yl)ethynyl)quinolin-6-yl)-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamide 
• 1551454-75-1 N-(5-(4-((1-(tert-butoxycarbonyl)-4-hydroxypiperidin-4-yl)ethynyl)quinolin-6-yl)-2-methoxy-pyridin-3-yl)-2,4-difluorobenzene sulfonamide 
• 1551453-53-2 2,4-difluoro-N-(5-(4-((4-hydroxypiperidin-4-yl)ethynyl)quinolin-6-yl)-2-methoxypyridin-3-yl)benzenesulfonamide 

Relevant articles and documents

GNE-886: A Potent and Selective Inhibitor of the Cat Eye Syndrome Chromosome Region Candidate 2 Bromodomain (CECR2)

The biological function of bromodomains, epigenetic readers of acetylated lysine residues, remains largely unknown. Herein we report our efforts to discover a potent and selective inhibitor of the bromodomain of cat eye syndrome chromosome region candidate 2 (CECR2). Screening of our internal medicinal chemistry collection led to the identification of a pyrrolopyridone chemical lead, and subsequent structure-based drug design led to a potent and selective CECR2 bromodomain inhibitor (GNE-886) suitable for use as an in vitro tool compound.

Inhibition of bromodomain-containing protein 9 for the prevention of epigenetically-defined drug resistance

Bromodomain-containing protein 9 (BRD9), an epigenetic “reader” of acetylated lysines on post-translationally modified histone proteins, is upregulated in multiple cancer cell lines. To assess the functional role of BRD9 in cancer cell lines, we identified a small-molecule inhibitor of the BRD9 bromodomain. Starting from a pyrrolopyridone lead, we used structure-based drug design to identify a potent and highly selective in vitro tool compound 11, (GNE-375). While this compound showed minimal effects in cell viability or gene expression assays, it showed remarkable potency in preventing the emergence of a drug tolerant population in EGFR mutant PC9 cells treated with EGFR inhibitors. Such tolerance has been linked to an altered epigenetic state, and 11 decreased BRD9 binding to chromatin, and this was associated with decreased expression of ALDH1A1, a gene previously shown to be important in drug tolerance. BRD9 inhibitors may therefore show utility in preventing epigenetically-defined drug resistance.

SUBSTITUTED PYRROLOPYRIDINES AS INHIBITORS OF BROMODOMAIN

The present invention relates to compounds of formula (I) and to salts thereof, wherein R1, R2, and Q have any of the values defined in the specification, and compositions and uses thereof. The compounds are useful as inhibitors of bromodomains. Also included are pharmaceutical compositions comprising a compound of formula (I) or a pharmaceutically acceptable salt thereof, and methods of using such compounds and salts in the treatment of various bromodomain-mediated disorders.