82827-09-6 | 6-Bromoisoquinolin-1-ol

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$20.00	$14.00
5g	95%	in stock	$39.00	$28.00
10g	95%	in stock	$70.00	$49.00

Description

• Catalog Number: AB45399
• Chemical Name: 6-Bromoisoquinolin-1-ol
• CAS Number: 82827-09-6
• Molecular Formula: C9H6BrNO
• Molecular Weight: 224.054
• MDL Number: MFCD07374394
• SMILES: Brc1ccc2c(c1)cc[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 6-bromoisoquinolin-1-ol, commence with aniline as the starting material. Subject aniline to a Skraup Synthesis by treating it with glycerol and sulfuric acid under reflux, introducing an oxidizing agent such as nitrobenzene. This sequence will yield the parent heterocycle, isoquinoline.

Next, selectively hydroxylate the isoquinoline at the 1-position through a regioselective acid-catalyzed Friedel-Crafts alkylation using ethanol under carefully controlled conditions, resulting in ethylated isoquinolin-1-ol. Follow this with hydrolysis to obtain isoquinolin-1-ol.

Introduce bromine at the 6-position via a halogenation reaction, employing N-bromosuccinimide (NBS) in the presence of a radical initiator like azobisisobutyronitrile (AIBN) or ultraviolet light, and an appropriate solvent such as carbon tetrachloride. The reaction proceeds via radical substitution to afford 6-bromoisoquinolin-1-ol.

Purify the final compound by crystallization or column chromatography, confirming the structure via NMR, IR, and mass spectrometry. The overall success of the synthesis will depend on precise temperature control and reaction timing to ensure regioselectivity and yield optimization.