105679-22-9 | 7-bromo-3,4-dihydro-2H-1,4-benzoxazine

Packsize	Purity	Availability	Price	Discounted Price
100mg	97%	in stock	$10.00	$7.00
250mg	97%	in stock	$16.00	$12.00
1g	97%	in stock	$23.00	$16.00
5g	97%	in stock	$110.00	$77.00
10g	97%	in stock	$215.00	$150.00
25g	97%	in stock	$518.00	$362.00

Description

• Catalog Number: AD78450
• Chemical Name: 7-bromo-3,4-dihydro-2H-1,4-benzoxazine
• CAS Number: 105679-22-9
• Molecular Formula: C8H8BrNO
• Molecular Weight: 214.05922000000004
• MDL Number: MFCD09056750
• SMILES: Brc1ccc2c(c1)OCCN2

Computed Properties

• Complexity: 142
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• XLogP3: 2.3

Upstream Synthesis Route

To synthesize 7-bromo-3,4-dihydro-2H-1,4-benzoxazine, you would begin with the key starting material 2-aminophenol. Here is the synthesis route:

1. **Bromination of Phenol**: Start with 2-aminophenol and brominate it using bromine in an appropriate solvent like dichloromethane to obtain 6-bromo-2-aminophenol.

2. **Protection of Amine**: Protect the amine group in 6-bromo-2-aminophenol by reacting it with a protection reagent such as an acyl chloride (e.g., acetyl chloride) to yield N-acetyl-6-bromo-2-aminophenol.

3. **Formation of Benzoxazine Ring**: Conduct a ring-closure reaction by treating the protected aminophenol with an epoxide like ethylene oxide in the presence of a base (e.g., sodium hydroxide) to form the benzoxazine ring, resulting in a compound structurally known as 3,4-dihydro-2H-1,4-benzoxazine.

4. **Bromination at position 7**: Subject the 3,4-dihydro-2H-1,4-benzoxazine to further bromination to introduce the bromo group at position 7 of the benzoxazine ring. This can be achieved using N-bromosuccinimide (NBS) in the presence of a radical initiator, typically under light or heat conditions.

5. **Deprotection of the Amine**: Lastly, remove the protecting group from the amine. For the acetyl-protected amine, apply acidic conditions (e.g., hydrochloric acid) to yield the target molecule, 7-bromo-3,4-dihydro-2H-1,4-benzoxazine.

Please note, the specific conditions such as temperature, solvent, and stoichiometry will need to be optimized for each step. It's also essential to purify the intermediate products after each step via appropriate methods like column chromatography or recrystallization.