934-05-4 | Methyl 4-bromo-1H-pyrrole-2-carboxylate

Packsize	Purity	Availability	Price	Discounted Price
1g	98%	in stock	$8.00	$5.00
5g	98%	in stock	$12.00	$8.00
10g	98%	in stock	$22.00	$15.00
25g	98%	in stock	$38.00	$26.00
100g	98%	in stock	$145.00	$101.00

Description

• Catalog Number: AB75863
• Chemical Name: Methyl 4-bromo-1H-pyrrole-2-carboxylate
• CAS Number: 934-05-4
• Molecular Formula: C6H6BrNO2
• Molecular Weight: 204.0213
• MDL Number: MFCD00832855
• SMILES: COC(=O)c1cc(c[nH]1)Br

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: 1.6

Upstream Synthesis Route

The upstream synthesis of Methyl 4-bromo-1H-pyrrole-2-carboxylate can be outlined as follows:

1. **Synthesis of Pyrrole**: The starting material would typically be a suitable amino acid such as glutamic acid, which undergoes Hofmann rearrangement to generate the corresponding aminoketone. Cyclization of this intermediate forms the pyrrole ring.

2. **Functionalization at Position 2**: The carboxylate group is introduced using a suitable derivatization reagent such as methyl chloroformate to form the methyl ester at position 2 of the pyrrole ring, yielding methyl pyrrole-2-carboxylate.

3. **Halogenation at Position 4**: The bromination step involves the electrophilic substitution of the hydrogen atom at position 4 of the pyrrole ring. This can be achieved by using N-bromosuccinimide (NBS) in the presence of a radical initiator such as AIBN (azobisisobutyronitrile) under suitable conditions, preferably with light or heat to generate the radical species.

Overall, the sequence involves constructing the pyrrole ring, esterification, followed by selective bromination at the 4-position to yield Methyl 4-bromo-1H-pyrrole-2-carboxylate. The specific conditions and solvents would depend on scale, desired purity, and yield optimization based on experimental data.

Literature

• Molecular cloning, structure, and reactivity of the second bromoperoxidase from Ascophyllum nodosum.

  Bioorganic chemistry 20121001