5498-31-7 | 1-Bromo-3-hydroxynaphthalene

Packsize	Purity	Availability	Price	Discounted Price
100mg	98%	in stock	$6.00	$5.00
250mg	98%	in stock	$11.00	$8.00
1g	98%	in stock	$14.00	$10.00
5g	98%	in stock	$45.00	$31.00
10g	98%	in stock	$76.00	$53.00
25g	98%	in stock	$168.00	$117.00

Description

• Catalog Number: AB49138
• Chemical Name: 1-Bromo-3-hydroxynaphthalene
• CAS Number: 5498-31-7
• Molecular Formula: C10H7BrO
• Molecular Weight: 223.066
• MDL Number: MFCD01712260
• SMILES: Oc1cc2ccccc2c(c1)Br

Computed Properties

• Complexity: 160
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 12
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• XLogP3: 3

Upstream Synthesis Route

The synthesis of 1-Bromo-3-hydroxynaphthalene can be achieved by following these steps:

1. Begin with 2-naphthol as the starting material.

2. Protect the hydroxyl group of 2-naphthol by converting it to its tert-butyldimethylsilyl (TBDMS) ether derivative using tert-butyldimethylsilyl chloride (TBDMSCl) and imidazole as a catalyst in anhydrous DMF or dichloromethane.

3. Subject the 2-naphthol TBDMS ether to bromination at the 1-position. This can be accomplished with the use of N-bromosuccinimide (NBS) in the presence of a radical initiator such as AIBN (azo-bis(isobutyronitrile)) in a suitable solvent like carbon tetrachloride (CCl4) or chloroform (CHCl3). The reaction is carried out under reflux conditions.

4. Following the bromination, remove the protecting group from the hydroxyl function. This deprotection can be executed with tetrabutylammonium fluoride (TBAF) in THF or with hydrochloric acid in methanol, yielding the desired 1-Bromo-3-hydroxynaphthalene.

5. Purify the 1-Bromo-3-hydroxynaphthalene through recrystallization or column chromatography, depending on the specific impurities present in the reaction mixture.

6. Verify the purity and structure of the final product using techniques like NMR (nuclear magnetic resonance), GC-MS (gas chromatography-mass spectrometry), and melting point determination.

Literature

• 3,3'-disubstituted BINAP ligands: synthesis, resolution, and applications in asymmetric hydrogenation.

  Organic letters 20050818