460746-47-8

Basic information

• Product Name: 4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE
• Synonyms: '-Hydroxy-3'-iodo[1,1'-biphenyl]-4-carbonitrile;4-(4-Hydroxy-3-iodophenyl)benzonitrile;[1,1'-Biphenyl]-4-carbonitrile, 4'-hydroxy-3'-iodo-
• CAS NO: 460746-47-8
• Molecular Formula: C₁₃H₈INO
• Molecular Weight: 321.12
• Mol File: 460746-47-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 166-167℃
• Boiling Point: 392.9±37.0 °C(Predicted)
• Appearance: /
• Density: 1.81
• Storage Temp.: 2-8°C(protect from light)
• PKA: 8.03±0.31(Predicted)
• CAS DataBase Reference: 4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE(460746-47-8)
• EPA Substance Registry System: 4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE(460746-47-8)

Safety Data

• Hazardous Substances Data: 460746-47-8(Hazardous Substances Data)

Usage

Description

4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE is an organic compound that serves as a significant byproduct in the synthesis of 4''-Hydroxy-3'',5''-diiodo-[1,1''-biphenyl]-4-carbonitrile (H005080). 4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE is a valuable building block in the pharmaceutical industry, particularly for the development of plasminogen activator inhibitor antagonists.

Uses

Used in Pharmaceutical Industry:
4'-HYDROXY-3'-IODO-BIPHENYL-4-CARBONITRILE is used as a building block compound for the development of plasminogen activator inhibitor antagonists. These antagonists are crucial in the treatment of various medical conditions, such as thrombotic disorders and cardiovascular diseases, by inhibiting the activity of plasminogen activator inhibitors.
Additionally, this compound is used in the preparation of other pharmaceutical compounds, contributing to the advancement of drug discovery and development in the industry. Its unique structure and properties make it a promising candidate for further research and application in the field of medicine.

Upstream product

• 19812-93-2 4-Cyano-4'-hydroxybiphenyl 

Downstream Products

• 460746-48-9 4-[2-(2-hydroxyethyl)-1-benzofuran-5-yl]benzonitrile 
• 460746-46-7 4-{2-[2-(2R-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}benzonitrile 
• 460746-49-0 2-[5-(4-cyanophenyl)-1-benzofuran-2-yl]ethyl methanesulfonate 
• 670342-24-2 toluene-4-sulfonic acid 2-[5-(4-cyano-phenyl)benzofuran-2-yl]ethyl ester 
• 460748-71-4 4-{2-[2-((R)-2-methylpyrrolidin-1-yl)ethyl]benzofuran-5-yl}benzonitrile L-tartrate 
• 895542-09-3 3″-tert-butyl-4′-(2-hydroxy-ethoxy)-4″-pyrrolidin-1-yl-[1,1′;3′,1″]-terphenyl-4-carboxylic acid 

Relevant articles and documents

A facile and scaleable synthesis of ABT-239, a benzofuranoid H3 antagonist

A facile and scaleable synthesis of a potent and selective histamine H 3 receptor antagonist, ABT-239 (1), was developed starting from commercially available 4′-hydroxy-biphenyl-4-carbonitrile (2). The synthesis comprised four chemical steps and a salt formation step with an overall yield of 40%. A highly selective monoiodination of a phenol was developed and used to prepare iodophenol (3b) in near quantitative yield using NIS in AcOH in the presence of a small amount of H2SO4. A Pd-catalyzed cross coupling reaction of the iodophenols (3b) with butyn-3-ol (4a) provided benzofuran (5) in one step in >80% yield, en route to 1. The new process required no chromatographic purification throughout the synthesis and was successfully demonstrated on scale-up to prepare 1.7 kg of the target ABT-239 (1).

A new class of potent non-imidazole H3 antagonists: 2-Aminoethylbenzofurans

2-Aminoethylbenzofurans constitute a new class of H3 antagonists that are more rotationally constrained than most previously reported H3 antagonists. They retain high potency at human and rat receptors, with efficient CNS penetration observed in 35. The SAR of the basic amine moiety was compared in three different series of analogues. The greatest potency was found in analogues bearing a 2-methylpyrrolidine, a 2,5-dimethylpyrrolidine, or a 2,6-dimethylpiperidine.

1,3-disubstituted and 1,3,3-trisubstituted pyrrolidines as histamine-3 receptor ligands and their therapeutic applications

Compounds of formula I are useful in treating diseases or conditions prevented by or ameliorated with histamine-3 receptor ligands. Also disclosed are histamine-3 receptor ligand compositions and methods of antagonizing or agonizing histamine-3 receptors.