36953-41-0

Basic information

• Product Name: 3-Bromo-4-hydroxypyridine
• Synonyms: 3-BROMO-4-HYDROXYPYRIDINE;3-BROMO-4-PYRIDINOL;4-HYDROXY-3-BROMOPYRIDINE;3-BROMO-4-HYDROXYPYRIDINE 97%;3-Bromopyridin-4-ol;Synthesis of 3-bromopyridin-4-ol
• CAS NO: 36953-41-0
• Molecular Formula: C₅H₄BrNO
• Molecular Weight: 174
• Product Categories: Pyridine;Pyridines
• Mol File: 36953-41-0.mol

Chemical Properties

• Melting Point: 225-230℃
• Boiling Point: 244.3 °C at 760 mmHg
• Flash Point: 101.6 °C
• Appearance: /
• Density: 1.776 g/cm³
• Vapor Pressure: 0.0306mmHg at 25°C
• Refractive Index: 1.6
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 3.71±0.18(Predicted)
• CAS DataBase Reference: 3-Bromo-4-hydroxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Bromo-4-hydroxypyridine(36953-41-0)
• EPA Substance Registry System: 3-Bromo-4-hydroxypyridine(36953-41-0)

Safety Data

• Hazardous Substances Data: 36953-41-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-Bromo-4-hydroxypyridine is used as a key intermediate in the synthesis of various pharmaceuticals. Its unique structure and reactivity enable the development of new drugs with improved therapeutic properties.
Used in Agrochemical Industry:
3-Bromo-4-hydroxypyridine is utilized as a building block in the synthesis of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals.
Used in Organic Synthesis:
3-Bromo-4-hydroxypyridine is employed as a versatile reagent in organic synthesis, allowing the preparation of a wide range of functionalized pyridines with diverse applications.
Used in Medicinal Chemistry:
3-Bromo-4-hydroxypyridine is used as a valuable tool in medicinal chemistry, facilitating the design and synthesis of novel compounds with potential therapeutic applications.
Used in Research and Development:
3-Bromo-4-hydroxypyridine is studied for its potential biological activities, such as antifungal and antibacterial properties, making it an important target for further research and development in the field of drug discovery and therapeutic innovation.

InChI:InChI=1/C5H4BrNO/c6-4-3-7-2-1-5(4)8/h1-3H,(H,7,8)

Upstream product

• 1124-33-0 4-nitraminopyridine N-oxide 
• 626-64-2 pyridin-4-ol 
• 504-24-5 4-aminopyridine 
• 13534-98-0 3-bromopyridin-4-amine 
• 25813-25-6 3,5-dibromo-4-hydroxypyridine 

Downstream Products

• 1214377-46-4 3-bromo-4-(difluoromethoxy)pyridine 
• 868734-88-7 4-(2-fluoro-4-nitrophenoxyl)-3,3'-bipyridine 

Relevant articles and documents

Preparation method of pyridine derivative (by machine translation)

To the method, piperidine-4-one hydrochloride is used as a raw material, and a series of pyridine derivatives are obtained through halogenation reaction and elimination reaction. The reaction is eliminated by reacting piperidine-4-one hydrochloride with a specific amount of the 3,5 - halogenating agent in a halogenation 3, 3, 5 - reaction with a halogen-3, 3, 5, 5 - based reaction, followed by reaction with a pyridine derivative of a hydroxyl group, an amino group 4 - or a dimethylamino group, respectively, by eliminating the reaction with a different kind of basic agent. The method is simple and convenient to operate, mild in condition, short in technological process, low in waste water yield, environment-friendly, low in cost and beneficial to green industrial production of the pyridine derivative. (by machine translation)

Synthesis and biological evaluation of 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives as potential c-met inhibitors

Six series of novel 4-(2-fluorophenoxy)-3,3′-bipyridine derivatives conjugated with aza-aryl formamide/amine scaffords were designed and synthesized through a structure-based molecular hybridization approach. The target compounds were evaluated for c-Met kinase inhibitory activities and cytotoxicity against four cancer cell lines (HT-29, A549, MKN-45 and MDA-MB-231) in vitro. Most compounds exhibited moderate to excellent potency, and the most promising candidate 26c (c-Met kinase IC50 = 8.2 nM) showed a 4.7-fold increase in cytotoxicity against c-Met-addicted MKN-45 cell line in vitro (IC50 = 3 nM), superior to that of Foretinib (IC50 = 23 nM). The preliminary structure-activity relationship indicated that a 1H-benzo [e] [1,3,4]thiadiazine-3-carboxamide-4,4-dioxide moiety as linker contributed to the antitumor potency.

ALDOSTERONE SYNTHASE INHIBITORS

This invention relates to tricyclic triazole analogues of the formula I or their pharmaceutically acceptable salts, wherein the variable are defined herein. The inventive compounds selectively inhibit aldosterone synthetase. This invention also provides for pharmaceutical compositions comprising the compounds of Formula I or their salts as well as to methods for the treatment, amelioration or prevention of conditions that could be treated by inhibiting aldosterone synthetase.

MACROCYCLIC ANTAGONISTS OF THE MOTILIN RECEPTOR FOR TREATMENT OF GASTROINTESTINAL DYSMOTILITY DISORDERS

The present invention provides conformationally-defined macrocyclic compounds that bind to and/or are functional modulators of the motilin receptor including subtypes, isoforms and/or variants thereof. These macrocyclic compounds, at a minimum, possess adequate pharmacological properties to be useful as therapeutics for a range of disease indications. In particular, these compounds are useful for treatment and prevention of disorders characterized by hypermotilinemia and/or gastrointestinal hypermotility, including, but not limited to, diarrhea, cancer treatment-related diarrhea, cancer-induced diarrhea, chemotherapy-induced diarrhea, radiation enteritis, radiation-induced diarrhea, stress-induced diarrhea, chronic diarrhea, AIDS-related diarrhea, C. difficile associated diarrhea, traveller's diarrhea, diarrhea induced by graph versus host disease, other types of diarrhea, dyspepsia, irritable bowel syndrome, chemotherapy-induced nausea and vomiting (emesis) and post-operative nausea and vomiting and functional gastrointestinal disorders. In addition, the compounds possess utility for the treatment of diseases and disorders characterized by poor stomach or intestinal absorption, such as short bowel syndrome, celiac disease and cachexia. The compounds also have use for the treatment of inflammatory diseases and disorders of the gastrointestinal tract, such as inflammatory bowel disease, ulcerative colitis, Crohn's disease and pancreatitis. Accordingly, methods of treating such disorders and pharmaceutical compositions including compounds of the present invention are also provided.

Efficient regioselective preparation of monobromo and bromoiodo hydroxy pyridines from dibromoderivatives via bromine-lithium exchange

Annular dibromination of hydroxypyridines with NBS in acetonitrile followed by bromine-lithium exchange with RLi and subsequent trapping with H2O or I2 afforded monobromo and bromoiodo derivatives in a completely regioselective way. Iodination of bromo hydroxypyridines with NIS is totally regioselective.

Mild regioselective halogenation of activated pyridines with N-bromosuccinimide

Regioselective mono and dihalogenations of amino, hydroxy and methoxy pyridines (2-, 3-, and 4-substituted) as well as 2,6-dimethoxy pyridine with N-bromosuccinimide in different solvents have been studied. Reactivity of the substrates decreases in the order amino>hydroxy>methoxy and regioselectivity depends on the position of the substituent (2-substituted > 3-substituted). In most of the cases we obtained monobrominated derivatives regioselectively and in high yields. Hydroxy and amino pyridines can also be dibrominated in almost quantitative yield with 2 equivalents of NBS.