53710-17-1

Basic information

• Product Name: 2,6-Diiodopyridine
• Synonyms: 2,6-DIIODO-PYRIDINE
• CAS NO: 53710-17-1
• Molecular Formula: C₅H₃I₂N
• Molecular Weight: 330.89
• Product Categories: Pyridine;Heterocycle-Pyridine series;alkyl Iodine
• Mol File: 53710-17-1.mol

Chemical Properties

• Melting Point: 179-180°C
• Boiling Point: 316.796 °C at 760 mmHg
• Flash Point: 145.393 °C
• Appearance: /
• Density: 2.609 g/cm³
• Vapor Pressure: 0.001mmHg at 25°C
• Refractive Index: 1.721
• Storage Temp.: 2-8°C(protect from light)
• PKA: -1.54±0.10(Predicted)
• CAS DataBase Reference: 2,6-Diiodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-Diiodopyridine(53710-17-1)
• EPA Substance Registry System: 2,6-Diiodopyridine(53710-17-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 53710-17-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-Diiodopyridine is utilized as a building block for the synthesis of various pharmaceuticals, leveraging its unique structure and reactivity to create a range of medicinal compounds.
Used in Organic Compounds Synthesis:
In the field of organic chemistry, 2,6-Diiodopyridine serves as a key intermediate, contributing to the development of fine chemicals through its distinctive properties and chemical behavior.

InChI:InChI=1/C5H3I2N/c6-4-2-1-3-5(7)8-4/h1-3H

Upstream product

• 2402-78-0 2,6-dichloropyridine 
• 626-05-1 2,6-Dibromopyridine 

Downstream Products

• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 171820-16-9 4,4’-(pyridine-2,6-diyl)diphenol 
• 5453-67-8 2,6-bis(methoxycarbonyl)pyridine 
• 15862-18-7 5,5'-dibromo-2,2'-dipyridyl 
• 1042150-68-4 C₁₀H₆BrIN₂ 
• 223463-10-3 5,5''-dibromo-2,2',6',2''-terpyridine 
• 123640-38-0 2,6-bis(pyrazole)pyridine 
• 1347068-18-1 C₃₉H₃₉Br₂NO₂ 
• 1148-79-4 2,2':6,2''-terpyridine 
• 709643-15-2 2,6-bis(2'-bromophenyl)pyridine 
• 1160096-68-3 2,6-bis(4-(trifluoromethyl)phenyl)pyridine 

Relevant articles and documents

Homoleptic zincate-promoted room-temperature halogen-metal exchange of bromopyridines

Homoleptic lithium tri- and tetraalkyl zincates were reacted with a set of bromopyridines. Efficient and chemoselective bromine-metal exchanges were realized at room temperature with a substoichiometric amount of nBu 4ZnLi2·TMEDA reagent (1/3 equiv; TMEDA=N,N,N′,N′-tetramethylethylenediamine). This reactivity contrasted with that of tBu4ZnLi2·TMEDA, which was inefficient below one equivalent. DFT calculations allowed us to rationalize the formation of N...Li stabilized polypyridyl zincates in the reaction. The one-pot difunctionalization of dibromopyridines was also realized using the reagent stoichiometrically. The direct creation of C-Zn bonds in bromopyridines enabled us to perform efficient Negishi-type cross-couplings. Mild zincation! nBu4ZnLi2·TMEDA (in substoichiometric amounts) promoted efficient and chemoselective room-temperature bromine-metal exchange of a range of bromopyridines (see scheme). DFT calculations strongly supported the formation of a stabilized tripyridylzincate, which could be reacted with electrophiles or be directly involved in palladium-catalyzed cross-coupling reactions.

Desymmetrization of dichloroazaheterocycles

3,6-Dichloropyridizine 1a was converted in good yield into its mono-iodo derivative 1b when treated with a mixture of hydriodic acid and sodium iodide. Pure samples of the mono-iodo derivatives 2b, 3b and 4b could not be obtained from their corresponding dichlorinated precursors with these reagents. Compounds 1b and 4b underwent palladium catalysed Suzuki, Sonogashira and other coupling reactions.