13472-79-2

Basic information

• Product Name: 2-Hydroxy-5-iodopyridine
• Synonyms: 5-IODO-2(1H)-PYRIDONE;5-IODO-2-PYRIDINOL;5-IODO-PYRIDIN-2-OL;2-HYDROXY-5-IODOPYRIDINE;5-Iodo-2-pyridinol~5-Iodo-2(1H)-pyridone;5-Iodo-2-Hydroxypridine;5-Iodo-2(1H)-pyridone, 5-Iodo-2-pyridinol;5-Iodo-1,2-dihydropyridine-2-one
• CAS NO: 13472-79-2
• Molecular Formula: C₅H₄INO
• Molecular Weight: 221
• EINECS: -0
• Product Categories: Heterocyclic Series;Halides;Pyridines;Pyridine
• Mol File: 13472-79-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: 192-196 °C(lit.)
• Boiling Point: 379.2 °C at 760 mmHg
• Flash Point: 183.134 °C
• Appearance: Yellow/Crystalline Powder
• Density: 2.142 g/cm³
• Vapor Pressure: 0.000296mmHg at 25°C
• Refractive Index: 1.682
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 10.15±0.10(Predicted)
• Water Solubility: Insoluble in water.
• Sensitive: Light Sensitive
• BRN: 108752
• CAS DataBase Reference: 2-Hydroxy-5-iodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Hydroxy-5-iodopyridine(13472-79-2)
• EPA Substance Registry System: 2-Hydroxy-5-iodopyridine(13472-79-2)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 22-37/38-41
• Safety Statements: 26-36/39
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 13472-79-2(Hazardous Substances Data)

Usage

Description

2-Hydroxy-5-iodopyridine is an organic compound characterized by the presence of a hydroxyl group at the 2nd position and an iodine atom at the 5th position on a pyridine ring. It is a versatile intermediate in the synthesis of various chemical and pharmaceutical products due to its unique structural features.

Uses

Used in Organic Synthesis:
2-Hydroxy-5-iodopyridine is used as a key intermediate for the synthesis of a wide range of organic compounds. Its presence of a hydroxyl and iodine group allows for various chemical reactions, making it a valuable building block in the development of new molecules.
Used in Pharmaceutical Industry:
2-Hydroxy-5-iodopyridine is used as an important raw material in the pharmaceutical industry for the development of new drugs. Its unique structure can be exploited to create novel therapeutic agents with potential applications in various medical conditions.
Used in Agrochemicals:
In the agrochemical industry, 2-Hydroxy-5-iodopyridine is used as a crucial intermediate for the synthesis of various agrochemical products, such as pesticides and herbicides. Its chemical properties make it a valuable component in the development of effective and targeted agricultural solutions.
Used in Dye Industry:
2-Hydroxy-5-iodopyridine is also used in the dye industry as a vital intermediate for the production of various dyes and pigments. Its unique structure contributes to the development of new colorants with improved properties and performance characteristics.

InChI:InChI=1/C5H4INO/c6-4-1-2-5(8)7-3-4/h1-3H,(H,7,8)

Upstream product

• 13472-61-2 5-iodo-2-methoxypyridine 
• 4241-27-4 1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile 
• 504-29-0 2-aminopyridine 
• 142-08-5 2-hydroxypyridin 
• 20511-12-0 2-amino-5-iodopyridine 
• 142-08-5 2-Pyridone 

Downstream Products

• 60154-05-4 5-iodo-1-methyl-1,2-dihydropyridin-2-one 
• 33630-94-3 5-amino-2-hydroxypyridine 
• 13472-80-5 2-hydroxy-3,5-diiodopyridine 
• 76053-43-5 5-(4-chloro-phenyl)-pyridin-2-ol 
• 13131-02-7 1-phenyl-1H-pyridin-2-one 
• 53179-13-8 Pirfenidone 

Relevant articles and documents

A highly efficient Suzuki-Miyaura methylation of pyridines leading to the drug pirfenidone and its CD3 version (SD-560)

Efficient introduction of methyl or methyl-d3 into aromatic and heteroaromatic systems still presents a synthetic challenge. In particular, we were in search of a non-cryogenic synthesis of the 5-CD3 version of pirfenidone (4d, also known as Pirespa, Esbriet or Pirfenex), one of the two drugs approved to date for retarding idiopathic pulmonary fibrosis (IPF), a serious, rare and fatal lung disease, with a life expectancy of 3-5 years. The methyl-deuterated version of pirfenidone (4e, also known as SD-560) was designed with the objective of attenuating the rate of drug metabolism, and our goal was to find a green methylation route to avoid the environmental and economic impact of employing alkyllithium at cryogenic temperatures. The examination of several cross-coupling strategies for the introduction of methyl or methyl-d3 into methoxypyridine and pyridone systems culminated in two green and nearly quantitative Suzuki-Miyaura cross-coupling routes in the presence of RuPhos ligand: the first, using commercially available methyl boronic acid or its CD3 analog and the second, employing potassium methyl trifluoroborate or CD3BF3K, the latter obtained by a new route in 88% yield. This led, on a scale of tens of grams, to the synthesis of pirfenidone (4d) and its d3 analog, SD-560 (4e), at 99% isotopic purity.

Environmental friendly method for the iodination of moderately active arenes

An effective and environmental friendly method for the iodination of various moderately active methoxy arenes, phenols and anilines using hydrogen peroxide and acidified sodium periodate in aqueous ethanol medium is reported. The extent of iodination is e

An Efficient and Selective Method for the Preparation of Iodophenols

Direct iodination of a wide range of phenols may be achieved with unprecedented selectivity in aqueous alcohol solvents by the action of a reagent preparated in situ from sodium hypochlorite and sodium iodide.Para-substituted phenols (or ortho-substituted, when the para-position is already occupied) are obtained in fair to excellent yields by simple isolation techniques.The extent of iodination is easily controlled by stoichiometry.The technique is also useful with some anilines.