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
• Article Data: 2

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

General Description

2,6-Diiodopyridine is a chemical compound with the molecular formula C5H3I2N. It is a derivative of pyridine and is characterized by the presence of two iodine atoms on the 2 and 6 positions of the pyridine ring. 2,6-Diiodopyridine is a yellow crystalline solid and is primarily used as a building block in the synthesis of various pharmaceuticals and organic compounds. Its unique structure and reactivity make it a valuable intermediate in the production of fine chemicals and pharmaceuticals. It is important to handle 2,6-Diiodopyridine with caution as it is a hazardous material and can cause irritation to the skin, eyes, and respiratory system upon contact or inhalation.

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

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.