27746-03-8 | 4-Chloro-1h-pyrrole-2-carboxylic acid

Packsize	Purity	Availability	Price	Discounted Price
100mg	96%	in stock	$15.00	$11.00
250mg	96%	in stock	$21.00	$15.00
1g	96%	in stock	$78.00	$55.00
25g	96%	in stock	$1,875.00	$1,312.00

Description

• Catalog Number: AB32831
• Chemical Name: 4-Chloro-1h-pyrrole-2-carboxylic acid
• CAS Number: 27746-03-8
• Molecular Formula: C5H4ClNO2
• Molecular Weight: 145.5438
• MDL Number: MFCD07343826
• SMILES: OC(=O)c1cc(c[nH]1)Cl

Computed Properties

• Complexity: 128
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 9
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 2
• Rotatable Bond Count: 1
• XLogP3: 1.2

Upstream Synthesis Route

To synthesize 4-Chloro-1H-pyrrole-2-carboxylic acid, the following upstream route can be employed:

1. **Synthesis of Pyrrole**: Begin with succinonitrile as a starting material, which is reacted with ammonia and formaldehyde through a double Mannich reaction to form 2,5-diaminopyrrole.

2. **Halogenation**: Subject the 2,5-diaminopyrrole to halogenation using N-chlorosuccinimide in an acidic medium to introduce a chlorine atom at the 4-position, resulting in 4-chloro-1H-pyrrole.

3. **Oxidation**: Revise the 4-chloro-1H-pyrrole through oxidation of the 2-position using an appropriate oxidizing agent such as potassium permanganate (KMnO4) to afford the 4-chloro-1H-pyrrole-2-carboxylic acid.

It should be noted that each step needs to be carefully optimized for temperature, solvent choice, reaction time, and molar equivalents to achieve the desired purity and yield of the final product. Furthermore, throughout the process, use of inert atmosphere and protection from moisture may be necessary, especially during halogenation and oxidation steps to prevent undesired side reactions.

Literature

• Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

  Bioorganic & medicinal chemistry letters 20101101

• Virtual fragment screening for novel inhibitors of 6-phosphogluconate dehydrogenase.

  Bioorganic & medicinal chemistry 20100715