56448-22-7

Basic information

• Product Name: 5-phenyl-1H-pyrrole-3-carbaldehyde
• Synonyms: 5-phenyl-1H-pyrrole-3-carbaldehyde;Pyrrole Related Compound 4 (2-Phenyl-4-formylpyrrole);Vonoprazan Impurity 28;Vonoprazan Impurity Z;5-Phenyl-1H-pyrrole-3-carboxaldehyde
• CAS NO: 56448-22-7
• Molecular Formula: C₁₁H₉NO
• Molecular Weight: 171.19526
• EINECS: -0
• Mol File: 56448-22-7.mol
• Article Data: 10

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-phenyl-1H-pyrrole-3-carbaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 5-phenyl-1H-pyrrole-3-carbaldehyde(56448-22-7)
• EPA Substance Registry System: 5-phenyl-1H-pyrrole-3-carbaldehyde(56448-22-7)

Safety Data

• Hazardous Substances Data: 56448-22-7(Hazardous Substances Data)

Usage

Description

5-phenyl-1H-pyrrole-3-carbaldehyde is an organic compound with the molecular formula C12H9NO. It is characterized by its aromatic structure, featuring a phenyl group attached to a pyrrole ring with a formyl group at the 3-position. 5-phenyl-1H-pyrrole-3-carbaldehyde is known for its potential applications in various industries due to its unique chemical properties.

Uses

Used in Pharmaceutical Industry:
5-phenyl-1H-pyrrole-3-carbaldehyde is used as an intermediate in the synthesis of various pharmaceutical compounds. One of its notable applications is in the production of Vonoprazan, a competitive potassium acid blocker. Vonoprazan is a proton pump inhibitor (PPI) that helps in reducing the production of stomach acid, providing relief from conditions like gastroesophageal reflux disease (GERD) and peptic ulcers.
As an Impurity:
5-phenyl-1H-pyrrole-3-carbaldehyde is also recognized as an impurity in the synthesis of Vonoprazan. The presence of this compound can affect the purity and efficacy of the final product. Therefore, it is essential to monitor and control the levels of 5-phenyl-1H-pyrrole-3-carbaldehyde during the manufacturing process to ensure the quality and safety of Vonoprazan.
While the provided materials do not mention other specific applications of 5-phenyl-1H-pyrrole-3-carbaldehyde, it is worth noting that compounds with similar structures are often explored for their potential use in various fields, such as materials science, agrochemistry, and the development of new drugs. Further research and development could potentially reveal additional applications for this compound in different industries.

Upstream product

• 1240491-46-6 ethyl 3-(((E)-(1-phenylethylidene)amino)oxy)acrylate 
• 10341-75-0 (E)-1-phenylethanone oxime 
• 7126-39-8 pyrrole-3-carboxaldehyde 
• 881676-32-0 5-bromo-1H-pyrrole-3-carboxaldehyde 
• 98-80-6 phenylboronic acid 
• 161958-61-8 ethyl 5-phenyl-1H-pyrrole-3-carboxylate 
• 158692-57-0 Ethyl 2-chloro-5-phenyl-1H-pyrrole-3-carboxylate 
• 70-11-1 α-bromoacetophenone 
• 22984-74-3 Ethyl 2-cyano-4-oxo-4-phenylbutanoate 
• 114615-82-6 tetrapropylammonium perruthennate 
• 881673-95-6 (5-phenyl-1H-pyrrol-3-yl)methanol 
• 110-00-9 furan 
• 2227-79-4 benzenecarbothioamide 

Downstream Products

• 1100364-04-2 C₁₅H₁₇NO₂ 
• 881676-61-5 2-[(4-formyl-2-phenyl-1H-pyrrol-1-yl)sulfonyl]benzonitrile 
• 881676-90-0 5-phenyl-1-(pyridin-3-ylsulfonyl)-1H-pyrrole-3-carbaldehyde 
• 881676-06-8 5-phenyl-1-(2-thienylsulfonyl)-1H-pyrrole-3-carbaldehyde 
• 881678-95-1 1-{1-[(3-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}-N-methylmethanamine hydrochloride 
• 1374671-90-5 N-methyl-1-[5-phenyl-1-(pyridin-2-ylsulfonyl)-1H-pyrrol-3-yl]methanamine hydrochloride 
• 881673-96-7 tert-butyl methyl[(5-phenyl-1H-pyrrol-3-yl)methyl]-carbamate 
• 1374671-88-1 tert-butyl ({1-[(3-methoxyphenyl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate 
• 881678-28-0 tert-butyl ({[1-(6-chloropyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate 
• 1374671-92-7 tert-butyl ({[1-(6-cyanopyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrol-3-yl}methyl)methylcarbamate 

Relevant articles and documents

A Practical route to substituted 7-aminoindoles from pyrrole-3-carboxaldehydes

Among privileged structures, indoles occupy a central place in medicinal chemistry and alkaloid research. Here we report a flexible and efficient conversion of pyrrole-3-carboxaldehydes to substituted 7-amino-5-cyanoindoles. Phosphine addition to fumaronitrile proceeds with prototropic rearrangement of the initially formed zwitterion to the thermodynamically favored phosphonium ylide, which is poised for in situ Wittig olefination. The predominantly E-alkene product positions the allylic nitrile for facile intramolecular Hoeben-Hoesch reaction in the presence of BF3·OEt2. Syntheses of 2,5- and 3,5-disubstituted 7-aminoindoles are illustrated. Additionally, dianion alkylation of the allylic nitrile is demonstrated to furnish, after cyclization, 5,6-disubstituted 7-aminoindoles to further exemplify this scalable and high-yielding method.

Synthesis of 2-bromo-and 2-phenyl-neo-confused porphyrins

Neo-confused porphyrins (neo-CPs), porphyrin isomers with a 1,3-connected pyrrolic subunit, are aromatic structures with a CNNN coordination core. Previously, examples of neo-CPs with fused benzo units or electron-withdrawing ester substituents have been

Discovery of a novel pyrrole derivative 1-[5-(2-fluorophenyl)-1-(pyridin-3- ylsulfonyl)-1 H -pyrrol-3-yl]- n -methylmethanamine fumarate (tak-438) as a Potassium-Competitive Acid Blocker (P-CAB)

In our pursuit of developing a novel and potent potassium-competitive acid blocker (P-CAB), we synthesized pyrrole derivatives focusing on compounds with low log"‰D and high ligand-lipophilicity efficiency (LLE) values. Among the compounds synthesized, the compound 13e exhibited potent H +,K+-ATPase inhibitory activity and potent gastric acid secretion inhibitory action in vivo. Its maximum efficacy was more potent and its duration of action was much longer than those of proton pump inhibitors (PPIs). Therefore, compound 13e (1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)- 1H-pyrrol-3-yl]-N-methylmethanamine fumarate, TAK-438) was selected as a drug candidate for the treatment of gastroesophageal reflux disease (GERD), peptic ulcer, and other acid-related diseases.