884494-49-9 | 2-Chloro-5-fluoro-4-iodopyridine

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$6.00	$4.00
250mg	98%	in stock	$8.00	$6.00
1g	95%	in stock	$9.00	$7.00
5g	≥98%	in stock	$16.00	$11.00
10g	≥98%	in stock	$29.00	$20.00

Description

• Catalog Number: AB61745
• Chemical Name: 2-Chloro-5-fluoro-4-iodopyridine
• CAS Number: 884494-49-9
• Molecular Formula: C5H2ClFIN
• Molecular Weight: 257.4320
• MDL Number: MFCD03095306
• SMILES: Clc1ncc(c(c1)I)F

Computed Properties

• Complexity: 103
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 2
• XLogP3: 2.6

Upstream Synthesis Route

To synthesize 2-Chloro-5-fluoro-4-iodopyridine, one can begin with a suitable pyridine derivative and sequentially introduce the halogens through halogenation reactions. A possible precursor for the synthesis would be pyridine itself or a pyridine derivative that already contains one of the substituents, such as 2-chloropyridine or 5-fluoropyridine.

1. Starting with pyridine, the first step would involve the selective halogenation at the 2-position. This can be achieved through an electrophilic aromatic substitution reaction using chlorine (Cl2) or a chlorinating agent such as N-Chlorosuccinimide (NCS) in the presence of a catalyst such as iron(III) chloride (FeCl3) to yield 2-chloropyridine.

2. Next, to introduce the fluorine at the 5-position, a directed lithiation using n-Butyllithium (n-BuLi) followed by an electrophilic fluorination with a fluorinating agent like Xenon difluoride (XeF2) or Silver(I) fluoride (AgF) would generate 2-chloro-5-fluoropyridine.

3. The final step would be the iodination at the 4-position. Given that iodination is generally less reactive compared to chlorination or fluorination, this can be accomplished by utilizing a milder iodinating agent such as Iodine monochloride (ICl) in the presence of an oxidant like Oxone® (potassium peroxymonosulfate) under controlled temperature conditions to afford the targeted 2-Chloro-5-fluoro-4-iodopyridine.

Each of these steps may require optimization concerning the reagents, reaction conditions like temperature and time, as well as post-reaction work-up and purification techniques, such as column chromatography or recrystallization, to obtain the desired compound in acceptable yield and purity. It should be noted that the order of halogenation might need to be adjusted based on the reactivity of the pyridine nucleus and the availability of precursors.