53700-93-9

Usage

Ester derivative

1H-Pyrrole-2-carboxylic acid This indicates that the compound is derived from 1H-pyrrole-2-carboxylic acid, which is a five-membered aromatic ring with a carboxyl group attached to it.

Aromatic and functional properties

The compound has an aromatic ring structure, which gives it a distinctive smell and chemical reactivity. It also has functional groups that can react with other molecules, making it useful in organic synthesis.

Phenylmethyl ester group

A phenyl group (a six-membered ring with delocalized electrons) attached to a methyl group (a single carbon atom with three hydrogen atoms) through an ester bond. This group gives the compound unique chemical characteristics and reactivity.

Commonly used in organic synthesis and pharmaceutical research

The compound is often used in the synthesis of other organic compounds and in the development of new drugs.

Potential applications

The compound has a wide range of potential uses, including drug development, material science, and other industries.

Upstream product

• 108-24-7 acetic anhydride 
• 3284-46-6 benzyl-3-methylpyrrole-2-carboxylate 

Relevant academic research and scientific papers

Syntheses and some chemistry of 1,2- and 1,1-bis(2-pyrrolyl)ethenes

trans-1,2-Bis(2-pyrrolyl)ethenes (e.g. 18-20) are prepared by McMurry-type reductive coupling of the corresponding 2-formylpyrroles. The isomeric 1,1-bis(2-pyrrolyl)ethenes (e.g. 24) are prepared as a minor byproduct in the reaction of 2-unsubstituted pyrroles (e.g. 22) with acetic anhydride under Friedel-Crafts conditions; the major product, as expected is the 2-acetylpyrrole 23. However, 5-(chloromethyl)dipyrromethanes (e.g. 35) can be obtained in high yield by reaction of 2-unsubstituted pyrroles 22 with chloroacetaldehyde diethyl acetal. Base-catalyzed elimination of HCl from 35 affords the 1,1-bis(2-pyrrolyl)ethene 24 along with the trans- and cis-1,2-bis(2-pyrrolyl)-ethenes 18 and 36, respectively. Conditions are optimized to afford a 66% yield of the 1,1-bis(2-pyrrolyl)ethene 24. In neutral organic solvents, 1,1-bis(2-pyrrolyl)ethenes exist in the ethene tautomeric form 2, rather than as the corresponding 5-methyldipyrromethene isomer 3; however, under acidic conditions, the 5-methyldipyrromethene salt 38 is observed, and the 5-methyl group undergoes acid-catalyzed exchange in deuterated solvents. 1,1-Bis(2-pyrrolyl)ethenes (e.g. 24) undergo standard chemistry, such as catalytic hydrogenation (Adams catalyst) of the alkene bond (to give 5-methyldipyrromethane 44), Vilsmeier formylation [to give 2-formyl-1,1-bis(2-pyrrolyl)-ethene 57], and reaction with Eschenmoser's salt (N,N-dimethyl(methylene)ammonium iodide) [to give 2-((N,N-dimethylamino)methyl)-1,1-bis(2-pyrrolyl)ethene 59]. Both the 5-methyldipyrromethane-1,9-dicarboxylic acid 45 and the 1,1-bis(5-carboxy-3,4-dimethyl-2-pyrrolyl)ethene 53 react with the 1,9-diformyldipyrromethane 46, under standard MacDonald conditions, to give 3,5,8-trimethyldeuteroporphyrin IX dimethyl ester 47.