223463-13-6 | 5-Bromo-2-iodopyridine

Packsize	Purity	Availability	Price	Discounted Price
5g	98%	in stock	$8.00	$5.00
25g	98%	in stock	$26.00	$18.00
100g	98%	in stock	$78.00	$54.00

Description

• Catalog Number: AB49542
• Chemical Name: 5-Bromo-2-iodopyridine
• CAS Number: 223463-13-6
• Molecular Formula: C5H3BrIN
• Molecular Weight: 283.8925
• MDL Number: MFCD00691506
• SMILES: Ic1ccc(cn1)Br

Computed Properties

• Complexity: 78.8
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 8
• Hydrogen Bond Acceptor Count: 1
• XLogP3: 2.2

Upstream Synthesis Route

The synthesis route for 5-bromo-2-iodopyridine typically starts with 2-bromopyridine as the starting material. The sequence of reactions can be summarized as follows:

1. Nitration: Treat 2-bromopyridine with a nitrating agent, such as a mixture of sulfuric acid and nitric acid, to introduce a nitro group at the 5-position, yielding 5-bromo-2-nitropyridine.

2. Reduction: Reduce the nitro group in 5-bromo-2-nitropyridine to an amino group using a reducing agent like palladium on carbon (Pd/C) with hydrogen gas or other suitable reducing conditions to afford 5-bromo-2-aminopyridine.

3. Diazotization: Convert the amino group in 5-bromo-2-aminopyridine to a diazonium salt via diazotization, typically using sodium nitrite (NaNO2) and an acid, such as hydrochloric acid (HCl), at low temperatures.

4. Sandmeyer Reaction: The diazonium group is then subjected to a Sandmeyer reaction by treating it with copper(I) iodide (CuI) to introduce the iodine substituent at the position of the diazonium group, resulting in the formation of 5-bromo-2-iodopyridine.

Each step in this synthetic route requires careful control of reaction conditions and purification of intermediates to ensure a high yield of the final product.

Literature

• Synthesis of 5-bromopyridyl-2-magnesium chloride and its application in the synthesis of functionalized pyridines.

  Organic letters 20041223