156454-43-2 | 5-Bromo-7-methyl-1H-indazole

Packsize	Purity	Availability	Price	Discounted Price
1g	97%	in stock	$15.00	$10.00
5g	97%	in stock	$42.00	$30.00
10g	97%	in stock	$67.00	$47.00
100g	97%	in stock	$665.00	$466.00

Description

• Catalog Number: AA78512
• Chemical Name: 5-Bromo-7-methyl-1H-indazole
• CAS Number: 156454-43-2
• Molecular Formula: C8H7BrN2
• Molecular Weight: 211.05858
• MDL Number: MFCD18206295
• SMILES: Brc1cc(C)c2c(c1)cn[nH]2

Computed Properties

• Complexity: 151
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 11
• Hydrogen Bond Acceptor Count: 1
• Hydrogen Bond Donor Count: 1
• XLogP3: 2.6

Upstream Synthesis Route

The upstream synthesis of 5-Bromo-7-methyl-1H-indazole typically involves the construction of the indazole nucleus followed by the selective introduction of bromine and methyl groups at the appropriate positions. A plausible synthetic route is as follows:

1. Start with ortho-nitrotoluene as the precursor for methyl group introduction. Perform a nitrile formation through reaction with chloroacetic acid followed by cyclization into a 2-methyl-5-nitrophenyl-1H-indazole through base-induced ring closure.

2. Reduce the nitro group to an amine using catalytic hydrogenation or through alternative reductants such as iron/HCl.

3. Diazotize the resulting amine with sodium nitrite and hydrochloric acid to form the diazonium salt.

4. Undergo a Sandmeyer reaction by treating the diazonium salt with copper(I) bromide (CuBr) to introduce the bromo substituent, yielding 5-bromo-7-methyl-1H-indazole.

This synthesis must be carried out with careful control of reagents and conditions to ensure regioselectivity, especially for the bromination step. Further purification steps may involve column chromatography, recrystallization, or other typical organic purification procedures to achieve the desired product purity.