15164-44-0 | 4-Iodobenzaldehyde

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$10.00	$7.00
5g	98%	in stock	$13.00	$9.00
10g	98%	in stock	$16.00	$11.00
25g	98%	in stock	$35.00	$24.00
100g	98%	in stock	$119.00	$83.00

Description

• Catalog Number: AB67724
• Chemical Name: 4-Iodobenzaldehyde
• CAS Number: 15164-44-0
• Molecular Formula: C7H5IO
• Molecular Weight: 232.0185
• MDL Number: MFCD00039576
• SMILES: O=Cc1ccc(cc1)I
• NSC Number: 84301

Computed Properties

• Complexity: 95.1
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 2.7

Upstream Synthesis Route

The upstream synthesis of 4-Iodobenzaldehyde can be achieved via the following route:

1. Begin with the commercially available substrate, benzene.
2. Perform an electrophilic aromatic substitution with iodine in the presence of nitric acid and a catalyst like copper (III) chloride to selectively iodinate the benzene to form iodobenzene.
3. Subject the iodobenzene to a Friedel-Crafts acylation reaction using an anhydride, such as acetic anhydride or acetyl chloride, in the presence of a Lewis acid catalyst like aluminum chloride to introduce the formyl group, yielding 4-iodoacetophenone.
4. Oxidize 4-iodoacetophenone using an oxidizing agent like selenium dioxide or nitric acid, which should specifically oxidize the methyl group to an aldehyde without affecting the iodine substituent, thus obtaining the target compound, 4-iodobenzaldehyde.

Throughout the synthesis, temperature, stoichiometry, and reaction times must be carefully controlled to optimize yields and purity. Additionally, between steps, purification processes such as recrystallization or column chromatography may be necessary to achieve the desired purity of intermediates and the final product.

Literature

• Competing intermolecular interactions in some 'bridge-flipped' isomeric phenylhydrazones.

  Acta crystallographica. Section C, Crystal structure communications 20120701

• Gamma probes and their use in tumor detection in colorectal cancer.

  International seminars in surgical oncology : ISSO 20080101

• Hydrogen-bonded chains of rings in 3-iodobenzaldehyde 2,4-dinitrophenylhydrazone and 4-iodobenzaldehyde 2,4-dinitrophenylhydrazone, and a three-dimensional framework in 4-iodobenzaldehyde 4-nitrophenylhydrazone generated by the combination of N-H...O and C-H...O hydrogen bonds with iodo-nitro interactions.

  Acta crystallographica. Section C, Crystal structure communications 20040101

• Highly active thermomorphic fluorous palladacycle catalyst precursors for the Heck reaction; evidence for a palladium nanoparticle pathway.

  Organic letters 20020613