67713-23-9 | 2,6-Dibromobenzaldehyde

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$8.00	$5.00
5g	98%	in stock	$16.00	$12.00
10g	98%	in stock	$29.00	$21.00
25g	98%	in stock	$60.00	$42.00
50g	98%	in stock	$115.00	$80.00
100g	98%	in stock	$200.00	$140.00

Description

• Catalog Number: AD05901
• Chemical Name: 2,6-Dibromobenzaldehyde
• CAS Number: 67713-23-9
• Molecular Formula: C7H4Br2O
• Molecular Weight: 263.9141
• MDL Number: MFCD11040410
• SMILES: O=Cc1c(Br)cccc1Br

Computed Properties

• Complexity: 117
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 2.8

Upstream Synthesis Route

To synthesize 2,6-Dibromobenzaldehyde, start with benzene as the starting compound:

1. Nitration: Treat benzene with a mixture of concentrated sulfuric acid (H2SO4) and nitric acid (HNO3) to introduce a nitro group (-NO2), forming nitrobenzene.

2. Bromination: Subject nitrobenzene to bromination by adding bromine (Br2) in the presence of iron (Fe) or iron(III) bromide (FeBr3) as a catalyst, resulting in 3-bromo-nitrobenzene.

3. Ortho-directing activation: Facilitate regioselective bromination by employing a halogenation process. This involves the treatment with more bromine in the presence of a Lewis acid such as FeBr3, targeting the ortho position relative to the initial bromine atom and producing 2,6-dibromo-nitrobenzene.

4. Reduction: Reduce the nitro group to an amine by hydrogenation over a catalyst such as palladium on carbon (Pd/C) with hydrogen gas (H2) to yield 2,6-dibromoaniline.

5. Diazotization: Convert the amino group to a diazonium salt by treating 2,6-dibromoaniline with nitrous acid (generated in situ from sodium nitrite (NaNO2) and hydrochloric acid (HCl)).

6. Hydrolysis: The diazonium salt is then hydrolyzed to form the corresponding 2,6-dibromophenol.

7. Oxidation: The hydroxyl group of 2,6-dibromophenol is converted to an aldehyde group using an oxidizing agent, such as pyridinium chlorochromate (PCC), to yield 2,6-dibromobenzaldehyde.

This route optimizes the bromination step to ensure selectivity for the ortho positions and uses standard chemistry processes like nitration, reduction, diazotization, and oxidation to build the desired product.