107842-74-0

Basic information

• Product Name: 4-Amino-3-bromo-2-hydroxypyridine
• Synonyms: 4-Amino-3-bromo-2-hydroxypyridine;2(1H)-Pyridinone, 4-amino-3-bromo-;4-Amino-3-bromopyridin-2-ol;4-amino-3-bromo-1H-pyridin-2-one
• CAS NO: 107842-74-0
• Molecular Formula: C₅H₅BrN₂O
• Molecular Weight: 189.01
• Product Categories: Pyridines
• Mol File: 107842-74-0.mol

Chemical Properties

• Melting Point: 255-258 °C
• Boiling Point: 284.7 °C at 760 mmHg
• Flash Point: 126 °C
• Appearance: /
• Density: 1.826 g/cm³
• Vapor Pressure: 0.00293mmHg at 25°C
• Refractive Index: 1.635
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 10.00±0.10(Predicted)
• CAS DataBase Reference: 4-Amino-3-bromo-2-hydroxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Amino-3-bromo-2-hydroxypyridine(107842-74-0)
• EPA Substance Registry System: 4-Amino-3-bromo-2-hydroxypyridine(107842-74-0)

Safety Data

• Hazardous Substances Data: 107842-74-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Amino-3-bromo-2-hydroxypyridine is used as a key intermediate for the synthesis of pharmaceuticals, contributing to the development of new drug molecules due to its unique structural features and reactivity.
Used in Agrochemical Production:
In the agrochemical industry, 4-Amino-3-bromo-2-hydroxypyridine is utilized as a building block in the creation of various agrochemicals, playing a crucial role in the synthesis of compounds that can enhance crop protection and yield.
Used in Organic Compounds Synthesis:
4-Amino-3-bromo-2-hydroxypyridine serves as a versatile building block in the synthesis of a wide range of organic compounds, leveraging its functional groups to form diverse molecular structures with potential applications across various industries.
Used in Heterocyclic Compounds Production:
4-Amino-3-bromo-2-hydroxypyridine is also used as a valuable intermediate in the production of heterocyclic compounds, which are important in various fields such as medicine, materials science, and chemical research, due to their diverse chemical properties and potential applications.

InChI:InChI=1/C5H5BrN2O/c6-4-3(7)1-2-8-5(4)9/h1-2H,(H3,7,8,9)

Upstream product

• 504-24-5 4-aminopyridine 
• 1214900-01-2 2-(benzyloxy)pyridin-4-amine 
• 14432-12-3 4-Amino-2-chloropyridine 
• 38767-72-5 3-deazaC 

Downstream Products

• 107842-75-1 4-amino-3-bromo-1-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-2(1H)-pyridinone 

Relevant articles and documents

Concise Entries to 4-Halo-2-pyridones and 3-Bromo-4-halo-2-pyridones

Methods for the synthesis of both simple 4-halo-2-pyridones and more functionalized 3,4-di- and (3,4,5-tri)-halo-2-pyridones are described that are based on a combination of Sandmeyer and regioselective (copper-mediated) halogenation, with a 2-chloro or a 2-benzyloxy moiety serving as a masked 2-pyridone.

Synthesis, Antitumor Activity, and Antiviral Activity of 3-Substituted 3-Deazacytidines and 3-Substituted 3-Deazauridines

Novel 3-substituted analogues of 4-amino-1-β-D-ribofuranosyl-2(1H)-pyridinone (3-deazacytidine, 3) and 4-hydroxy-1-β-D-ribofuranosyl-2(1H)-pyridinone (3-deazauridine, 4) have been synthesized and tested for antitumor and antiviral activity.Thus the 3-chloro (9a), 3-bromo (9b), and 3-nitro (9c) analogues of 3 and the 3-chloro (9d), 3-bromo (9e), and 3-nitro (9f) analogues of 4 were prepared by standard glycosylating procedures.Novel requisite heterocycles 4-amino-3-chloro-2(1H)-pyridinone (7a) and 4-amino-3-bromo-2(1H)-pyridinone (7b) were prepared by halogenating4-amino-2(1H)-pyridinone (5).Requisite heterocycles 4-amino-3-nitro-2(1H)-pyridinone (7c), 3-chloro-4-hydroxy-2(1H)-pyridinone (7d), 3-bromo-4-hydroxy-2(1H)-pyridinone (7e), and 4-hydroxy-3-nitro-2(1H)-pyridinone (7f) were synthesized by known procedures from 4-hydroxy-2(1H)-pyridinone (6).Structure proof of target nucleosides was provided by independent synthesis, 1H NMR, and UV.Compounds 9a-f were devoid of activity against intraperitoneally implanted L1210 leukemia in mice.Compound 9f displayed significant activity against rhinovirus type 34 grown in WISH cells. 4-Amino-3-fluoro-1-β-D-ribofuranosyl-2(1H)-pyridinone (1) displayed good activity against intraperitoneally implanted P388 leukemia in mice, but it was devoid of activity against M5076 sarcoma, amelanotic (LOX) melanoma xenograft, and subrenal capsule human mammary carcinoma MX-1 xenograft in mice.Compound 1 also displayed significant activity against rhinovirus type 34.

4-amino-3-halo-2-pyridinone nucleoside and nucleotide compounds

4-Amino-3-halo-1-β-D-ribofuranosyl-2-(1H)-pyridinone, 4-amino-3-halo-1-(2-deoxy-β-D-pentofuranosyl)-2(1H)-pyridinone, and nucleosides and 4-amino-3-halo-1-(2-deoxy-2,2-difluoroβ-D-pentofuranosyl)-2(1H)-pyridinone nucleosides and nucleotides are useful as antiviral agents and possess in vivo activity against the L1210 murine leukemia cell line.