81190-89-8 | Methyl 4-bromo-1h-pyrazole-3-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$13.00	$9.00
5g	97%	in stock	$35.00	$24.00
10g	97%	in stock	$48.00	$34.00
25g	97%	in stock	$90.00	$63.00

Description

• Catalog Number: AA86090
• Chemical Name: Methyl 4-bromo-1h-pyrazole-3-carboxylate
• CAS Number: 81190-89-8
• Molecular Formula: C5H5BrN2O2
• Molecular Weight: 205.0094
• MDL Number: MFCD00619124
• SMILES: COC(=O)c1n[nH]cc1Br

Computed Properties

• Complexity: 142
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 2
• XLogP3: 1.1

Upstream Synthesis Route

The upstream synthesis of Methyl 4-bromo-1H-pyrazole-3-carboxylate typically involves the following steps:

1. Synthesis of Hydrazine Derivative: Begin with the preparation of an appropriate hydrazine derivative by reacting a diketone (often beta-keto ester) with hydrazine (NH2-NH2). For instance, ethyl acetoacetate can be used as the starting diketone.

2. Cyclization to Pyrazole: The resulting hydrazine derivative undergoes cyclization under acidic conditions to form the pyrazole ring, resulting in a compound such as 1H-pyrazole-3-carboxylic acid.

3. Esterification: The carboxylic acid group of the pyrazole compound is then esterified using methanol in the presence of an acid catalyst or by using diazomethane to yield methyl 1H-pyrazole-3-carboxylate.

4. Bromination: In the final step, the 4-position of the pyrazole ring is brominated. This can be achieved using brominating agents like N-bromosuccinimide (NBS) in the presence of a radical starter, typically under light irradiation or at elevated temperatures. The reaction typically takes place in a suitable solvent such as dichloromethane.

After purification, typically by column chromatography or recrystallization, the desired product, Methyl 4-bromo-1H-pyrazole-3-carboxylate, is obtained. It's important to note that the specific reaction conditions such as temperature, solvent, and reaction time are critical for the successful completion of each step and may require optimization for the best yield and purity.