796851-05-3 | 3-Chloro-2-fluoro-4-iodopyridine

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$13.00	$9.00
2g	98%	in stock	$25.00	$17.00
5g	98%	in stock	$36.00	$25.00
25g	95%	in stock	$174.00	$122.00
50g	95%	in stock	$345.00	$242.00
100g	95%	in stock	$684.00	$479.00
250g	95%	in stock	$1,709.00	$1,196.00

Description

• Catalog Number: AH70758
• Chemical Name: 3-Chloro-2-fluoro-4-iodopyridine
• CAS Number: 796851-05-3
• Molecular Formula: C5H2ClFIN
• Molecular Weight: 257.4320
• MDL Number: MFCD16610366
• SMILES: Ic1ccnc(c1Cl)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

The synthesis of 3-Chloro-2-fluoro-4-iodopyridine can be approached using a multi-step synthesis route starting from a simple pyridine derivative:

1. **Starting Material**: Begin with 2-fluoropyridine as the starting material due to the difficulty of introducing fluorine onto aromatic rings.

2. **Halogenation at the 3-Position**: Perform a regioselective chlorination to introduce the chlorine at the 3-position. This can be achieved using N-Chlorosuccinimide (NCS) under mild conditions to avoid substitution of the fluorine already present.

3. **Functional Group Transformation**: To introduce iodine at the 4-position, the ring needs an activating and directing group since direct iodination of pyridine is challenging due to its decreased nucleophilicity. Therefore, a temporary directing group such as a nitro group can be introduced at the 4-position.

4. **Nitration**: The next step could be the nitration of 3-chloro-2-fluoropyridine using a mixture of nitric acid and sulfuric acid to afford 4-nitro-3-chloro-2-fluoropyridine as an intermediate.

5. **Reduction of Nitro Group**: The nitro group in the 4-position can then be reduced to an aniline using a suitable reducing agent, such as iron/hydrochloric acid or tin/chloride, to yield the 4-amino-3-chloro-2-fluoropyridine.

6. **Diazotization and Replacement with Iodide**: Convert the amino group to a diazonium salt through diazotization with sodium nitrite and hydrochloric acid. The diazonium group can then be replaced by an iodide using copper(I) iodide, sodium iodide in the presence of potassium iodide, or by the Sandmeyer reaction to form the desired 3-chloro-2-fluoro-4-iodopyridine.

7. **Purification**: Purify the final product by recrystallization or column chromatography, depending on the specific conditions and by-products formed during synthesis.

Throughout this multi-step synthesis, monitoring the progress at each stage using techniques such as NMR, IR, GC-MS, and TLC is crucial for confirmation of the structures and the purity of the intermediates and the final target compound.