29124-57-0 | 2-Amino-5-bromobenzaldehyde

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$5.00	$4.00
250mg	98%	in stock	$10.00	$7.00
1g	98%	in stock	$13.00	$10.00
5g	98%	in stock	$37.00	$26.00

Description

• Catalog Number: AB36411
• Chemical Name: 2-Amino-5-bromobenzaldehyde
• CAS Number: 29124-57-0
• Molecular Formula: C7H6BrNO
• Molecular Weight: 200.0326
• MDL Number: MFCD10696879
• SMILES: O=Cc1cc(Br)ccc1N

Computed Properties

• Complexity: 129
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 1.9

Upstream Synthesis Route

The upstream synthesis of 2-Amino-5-bromobenzaldehyde generally involves the functionalization of a suitable benzene derivative. A common route would utilize 2-nitroaniline as a starting material, which undergoes bromination followed by reduction and formylation steps:

1. Bromination: 2-Nitroaniline is treated with bromine in an acidic medium, typically acetic acid, to yield 5-bromo-2-nitroaniline.

2. Reduction: The nitro group of 5-bromo-2-nitroaniline is then catalytically reduced, usually using hydrogen gas in the presence of a palladium on carbon (Pd/C) catalyst, to give 5-bromo-2-aniline.

3. Formylation: The benzene ring of 5-bromo-2-aniline is then subjected to formylation using Vilsmeier-Haack reagent, a combination of DMF (N,N-dimethylformamide) and POCl3 (phosphorus oxychloride), to form the desired 2-amino-5-bromobenzaldehyde.

This synthesis route yields the target compound through halogenation, reduction, and formylation steps, utilizing intermediate purification where necessary to remove by-products and unreacted starting materials.

Literature

• Friedländer approach for the incorporation of 6-bromoquinoline into novel chelating ligands.

  Organic letters 20030626