1194-96-3 | methyl 4-chloro-1H-pyrrole-2-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$41.00	$29.00
250mg	95%	in stock	$63.00	$45.00
1g	95%	in stock	$129.00	$91.00
5g	95%	in stock	$452.00	$317.00

Description

• Catalog Number: AA24038
• Chemical Name: methyl 4-chloro-1H-pyrrole-2-carboxylate
• CAS Number: 1194-96-3
• Molecular Formula: C6H6ClNO2
• Molecular Weight: 159.5703
• MDL Number: MFCD11176523
• SMILES: COC(=O)c1cc(c[nH]1)Cl

Computed Properties

• Complexity: 140
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 10
• Hydrogen Bond Acceptor Count: 2
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 2
• XLogP3: 1.5

Upstream Synthesis Route

To synthesize methyl 4-chloro-1H-pyrrole-2-carboxylate, the following upstream synthesis route may be employed:

1. Start with 2-chloropyrrole as the starting material, which can be prepared by reacting succinimide with phosphorus pentachloride (PCl5) followed by dehydrohalogenation.

2. Then, perform a Vilsmeier-Haack formylation on 2-chloropyrrole using dimethylformamide (DMF) and phosphorus oxychloride (POCl3) to introduce the formyl group at the 1-position, yielding 1-formyl-2-chloropyrrole.

3. The formyl group of 1-formyl-2-chloropyrrole can be reduced to an alcohol using a reducing agent like sodium borohydride (NaBH4).

4. Oxidize the resulting alcohol to carboxylic acid by employing an oxidant such as potassium permanganate (KMnO4) or Jones reagent (CrO3/H2SO4 in acetone).

5. Finally, esterify the 4-chloro-1H-pyrrole-2-carboxylic acid with methanol using an acid catalyst like sulfuric acid or a coupling reagent like 1,3-dicyclohexylcarbodiimide (DCC) to obtain the desired product, methyl 4-chloro-1H-pyrrole-2-carboxylate.

Control of reaction conditions and purification steps, including distillation and recrystallization, may be necessary to ensure the purity of the final product.