162744-59-4 | 4-Bromo-2,6-difluorobenzyl alcohol

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$16.00	$11.00
5g	97%	in stock	$30.00	$21.00
10g	97%	in stock	$53.00	$37.00
25g	97%	in stock	$76.00	$54.00
100g	97%	in stock	$282.00	$197.00

Description

• Catalog Number: AA84562
• Chemical Name: 4-Bromo-2,6-difluorobenzyl alcohol
• CAS Number: 162744-59-4
• Molecular Formula: C7H5BrF2O
• Molecular Weight: 223.0148
• MDL Number: MFCD03094461
• SMILES: OCc1c(F)cc(cc1F)Br

Computed Properties

• Complexity: 122
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 1
• XLogP3: 1.9

Upstream Synthesis Route

The synthesis of 4-Bromo-2,6-difluorobenzyl alcohol can be approached by starting with commercially available 2,6-difluorobenzyl alcohol as the substrate.

1. The first step involves the selective bromination of the benzene ring. This can be accomplished by using a brominating agent such as N-bromosuccinimide (NBS) in the presence of a radical initiator like azobisisobutyronitrile (AIBN) under light or heat, to facilitate the formation of the radical species necessary for the substitution. The reaction is typically performed in a suitable solvent like carbon tetrachloride (CCl_4) or dichloromethane (DCM).

2. The second step proceeds through a free radical halogenation mechanism where the bromine radical generated from NBS selectively adds to the para position relative to the benzyl alcohol functionality, yielding 4-bromo-2,6-difluorobenzyl alcohol. The selectivity is driven by the electronic effects of the fluoro substituents which deactivate the ortho and meta positions and direct the electrophilic bromine to the para position.

3. The reaction is purged with an inert gas like nitrogen or argon to avoid side reactions involving oxygen.

4. After the completion of the reaction, the product is generally purified through column chromatography, utilizing an appropriate eluent system to separate the desired 4-bromo-2,6-difluorobenzyl alcohol from any side products and unreacted starting material.

Each step should be closely monitored by thin-layer chromatography (TLC) and the final product can be characterized by ^1H NMR, ^13C NMR, and mass spectroscopy to ensure the identity and purity of the synthesized 4-bromo-2,6-difluorobenzyl alcohol.