190777-77-6 | 5-Bromoisoquinolin-1-ol

Packsize	Purity	Availability	Price	Discounted Price
250mg	97%	in stock	$13.00	$9.00
1g	97%	in stock	$32.00	$22.00
5g	97%	in stock	$75.00	$52.00
10g	97%	in stock	$148.00	$103.00
25g	97%	in stock	$368.00	$257.00

Description

• Catalog Number: AB12310
• Chemical Name: 5-Bromoisoquinolin-1-ol
• CAS Number: 190777-77-6
• Molecular Formula: C9H6BrNO
• Molecular Weight: 224.0540
• MDL Number: MFCD11226915
• SMILES: Brc1cccc2c1cc[nH]c2=O

Computed Properties

• Complexity: 227
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• XLogP3: 2

Upstream Synthesis Route

To synthesize 5-Bromoisoquinolin-1-ol, one could employ a Skraup synthesis as the initial step. Begin with aniline, which acts as a starting material. Perform a condensation with glycerol under acidic conditions, typically sulfuric acid, in the presence of an oxidizing agent like nitrobenzene. This will yield the quinoline core structure.

Next, to introduce the bromine at the 5-position, carry out a halogenation reaction. Treat quinoline with bromine in the presence of a catalytic amount of Lewis acid like ferric chloride or aluminum chloride to selectively achieve 5-bromination, considering the directing effects of the nitrogen atom in the isoquinoline ring system.

Then proceed to functionalize the quinoline to the target isoquinoline derivative. This can be accomplished by heating the 5-bromoquinoline with formamide to induce cyclization, thus forming 5-bromoisoquinoline.

Following the formation of 5-bromoisoquinoline, oxidize it to 5-bromoisoquinoline-1-ol. This can be done through an appropriate oxidation reaction, such as using an oxidizing agent like N-bromosuccinimide (NBS) in the presence of a radical initiator under photolysis conditions to target the oxidation at the 1-position.

Carefully control conditions at each stage to minimize side reactions and optimize yields for the desired 5-Bromoisoquinolin-1-ol product.