53710-18-2

Basic information

• Product Name: 3,5-Diiodopyridine
• Synonyms: 3,5-Diiodopyridine;Pyridine, 3,5-diiodo-
• CAS NO: 53710-18-2
• Molecular Formula: C₅H₃I₂N
• Molecular Weight: 330.9
• Mol File: 53710-18-2.mol
• Article Data: 1

Chemical Properties

• Melting Point: 172℃
• Boiling Point: 317℃
• Flash Point: 154℃
• Appearance: /
• Density: 2.609
• Storage Temp.: 2-8°C(protect from light)
• PKA: 1.18±0.20(Predicted)
• CAS DataBase Reference: 3,5-Diiodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Diiodopyridine(53710-18-2)
• EPA Substance Registry System: 3,5-Diiodopyridine(53710-18-2)

Safety Data

• Hazardous Substances Data: 53710-18-2(Hazardous Substances Data)

Usage

General Description

3,5-Diiodopyridine is a chemical compound with the molecular formula C5H3I2N. It is a derivative of pyridine, which is a heterocyclic compound that contains a ring of five carbon atoms and one nitrogen atom. 3,5-Diiodopyridine is often used as a building block in the synthesis of various pharmaceutical and agrochemical products. It has a wide range of applications in organic synthesis, including its use as a reagent in the preparation of various compounds. This chemical has also been studied for its potential use in the development of new materials and is known for its strong electronegative properties due to the presence of the iodine atoms, making it a useful molecule in a variety of chemical reactions.

Upstream product

• 625-92-3 3,5-dibromopyridine 
• 110-86-1 pyridine 
• 7664-93-9 sulfuric acid 
• 7446-11-9 sulfur trioxide 
• 7553-56-2 iodine 

Downstream Products

• 25391-66-6 5-iodopyridin-3-ylamine 
• 879326-76-8 5-iodonicotinaldehyde 
• 1246767-44-1 3,5-bis(2-methoxyphenyl)pyridine 
• 15366-86-6 3,5-bis-(3-methoxyphenyl)-pyridine 
• 168426-25-3 3,5-bis(4-bromophenyl)pyridine 
• 171819-99-1 3,5-bis(4-fluorophenyl)pyridine 
• 26409-32-5 3,5-bis(4-methylphenyl)pyridine 
• 26409-33-6 3,5-bis-(4-methoxyphenyl)-pyridine 
• 92-52-4 biphenyl 
• 92-07-9 3,5-diphenylpyridine 
• 1436435-16-3 C₂₇H₂₄F₃NO₃S 
• 1436435-07-2 4-(5-isobutylpyridin-3-yl)-2-isopropylphenyl trifluoromethanesulfonate 

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.