474330-54-6 | Methyl 5-amino-2-bromo-4-methylbenzoate

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$26.00	$19.00
5g	98%	in stock	$129.00	$91.00
10g	98%	in stock	$253.00	$178.00
25g	98%	in stock	$534.00	$374.00

Description

• Catalog Number: AG32428
• Chemical Name: Methyl 5-amino-2-bromo-4-methylbenzoate
• CAS Number: 474330-54-6
• Molecular Formula: C9H10BrNO2
• Molecular Weight: 244.0852
• MDL Number: MFCD14706185
• SMILES: COC(=O)c1cc(N)c(cc1Br)C

Computed Properties

• Complexity: 198
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 2
• XLogP3: 2.1

Upstream Synthesis Route

The synthesis of Methyl 5-amino-2-bromo-4-methylbenzoate can be achieved through the following steps:

1. Start with 4-methylbenzoic acid as the starting material.
2. React the 4-methylbenzoic acid with thionyl chloride (SOCl2) to convert the carboxylic acid group to an acid chloride, resulting in 4-methylbenzoyl chloride.
3. Perform a Friedel-Crafts acylation using aluminum chloride (AlCl3) as a catalyst, reacting the 4-methylbenzoyl chloride with bromobenzene to introduce the bromine substituent, leading to 2-bromo-4-methylbenzophenone.
4. Brominate the 2-bromo-4-methylbenzophenone at the meta position relative to the ketone group using N-bromosuccinimide (NBS) in the presence of light or a radical initiator, to get 5-bromo-2-bromo-4-methylbenzophenone.
5. Carry out a reductive amination of the ketone group on 5-bromo-2-bromo-4-methylbenzophenone with ammonia and a reducing agent such as sodium cyanoborohydride (NaBH3CN) to introduce the amino group, forming 5-amino-2-bromo-4-methylbenzophenone.
6. Finally, esterify the resultant compound using methanol in the presence of an acid catalyst like sulfuric acid or hydrochloric acid to obtain the target compound, Methyl 5-amino-2-bromo-4-methylbenzoate.

Throughout the synthesis, purification steps involving techniques like column chromatography, recrystallization, or distillation may be necessary after each step to obtain products with the required purity for subsequent reactions. Additionally, protecting group strategies may be employed if necessary to prevent unwanted side reactions.