885523-08-0 | 6-Bromo-(1H)indazole-4-carboxylic acid

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$15.00	$11.00
5g	98%	in stock	$58.00	$41.00
10g	98%	in stock	$103.00	$73.00
25g	98%	in stock	$257.00	$180.00

Description

• Catalog Number: AB69702
• Chemical Name: 6-Bromo-(1H)indazole-4-carboxylic acid
• CAS Number: 885523-08-0
• Molecular Formula: C8H5BrN2O2
• Molecular Weight: 241.0415
• MDL Number: MFCD07368215
• SMILES: Brc1cc(C(=O)O)c2c(c1)[nH]nc2

Computed Properties

• Complexity: 224
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 13
• Hydrogen Bond Acceptor Count: 3
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1
• XLogP3: 1.8

Upstream Synthesis Route

The synthesis of 6-Bromo-(1H)indazole-4-carboxylic acid can be approached through several steps starting from simple precursors:

1. Begin with the synthesis of 4-aminobenzoic acid, which can be obtained via the nitration of benzoic acid followed by reduction of the nitro group to an amino group.

2. The next step involves the protection of the amino group using a suitable protecting group such as a Boc (tert-Butyloxycarbonyl) group under acidic conditions. This protection is crucial for the selective functionalization of the molecule in subsequent steps.

3. Carboxylic acid activation is then achieved by converting the 4-Boc-aminobenzoic acid to its corresponding acyl chloride using thionyl chloride.

4. Meanwhile, prepare the hydrazine precursor by bromination of phenyl hydrazine with N-bromosuccinimide (NBS) to yield 6-bromophenyl hydrazine.

5. Then, condense the activated 4-Boc-aminobenzoyl chloride with 6-bromophenyl hydrazine to form the hydrazone intermediate.

6. The indazole ring closure can be achieved through cyclization of the hydrazone intermediate under acidic conditions, typically involving polyphosphoric acid.

7. After the formation of the indazole core, the tert-butyl protecting group can be removed with trifluoroacetic acid (TFA) to yield the 6-Bromo-(1H)indazole-4-carboxylic acid.

Each step should be monitored by appropriate analytical methods such as NMR, LC-MS, or IR spectroscopy to ensure purity and correct structure of intermediates. Appropriate work-up and purification procedures including recrystallization, column chromatography or distillation depending on the specific reaction step must be performed to obtain the final desired product with high purity.