3243-24-1

Basic information

• Product Name: 4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one
• Synonyms: 1H-Imidazo[4,5-c]pyridin-4-ol;4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one;4H-IMidazo[4,5-c]pyridin-4-one, 3,5-dihydro-;1H-imidazo[4,5-c]pyridin-4(5H)-one;1,5-dihydro-imidazo[4,5-c]pyridin-4-one
• CAS NO: 3243-24-1
• Molecular Formula: C₆H₅N₃O
• Molecular Weight: 133.10752
• Mol File: 3243-24-1.mol

Chemical Properties

• Melting Point: 320 °C
• Boiling Point: 648.6 °C at 760 mmHg
• Flash Point: 346.1 °C
• Appearance: /
• Density: 1.443 g/cm³
• Vapor Pressure: 1.04E-16mmHg at 25°C
• Refractive Index: 1.647
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 10.67±0.20(Predicted)
• CAS DataBase Reference: 4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one(3243-24-1)
• EPA Substance Registry System: 4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one(3243-24-1)

Safety Data

• Hazardous Substances Data: 3243-24-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biochemical Research:
4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one is used as a coupling reagent for the synthesis of peptides and other complex organic molecules, facilitating the formation of amide and ester bonds. Its high reactivity and low racemization rates contribute to the production of peptides with high purity and yield, making it an essential tool in the development of new drugs and bioactive compounds.
Used in Chemical Synthesis:
In the chemical synthesis industry, 4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one is utilized as a potent reagent for amidation and esterification reactions. Its efficiency and solubility in common organic solvents make it suitable for a wide range of applications, including the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Peptide Synthesis:
4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one is used as a coupling reagent in peptide synthesis, enabling the formation of peptide bonds between amino acids. Its compatibility with N,N-diisopropylethylamine as a base enhances the reaction efficiency, leading to the production of peptides with high purity and minimal side reactions.
Used in Organic Chemistry Education:
In academic settings, 4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one serves as a valuable teaching aid in organic chemistry courses, demonstrating the principles of coupling reactions and the synthesis of complex organic molecules. Its non-toxic and easy-to-handle properties make it a safe choice for educational purposes.

InChI:InChI=1/C6H5N3O/c10-6-5-4(1-2-7-6)8-3-9-5/h1-3H,(H,7,10)(H,8,9)

Upstream product

• 39217-08-8 2-chloropyridine-3,4-diamine 

Downstream Products

• 82722-74-5 1,5-dihydro-7-nitro-4H-imidazo[4,5-c]pyridin-4-one 
• 253274-13-4 3-[3-(5-1,2,4-oxadiazol-3-yl)-benzyl]-4,5-dihydro-3H-imidazo[4,5-c]pyridin-4-one 
• 272-97-9 Imidazo<4,5-c>pyridin 
• 33631-02-6 3,4-diamino-pyridin-2-ol 
• 2770-01-6 4-chloro-1H-imidazo[4,5-c]pyridine 

Relevant articles and documents

Scaffold Hopping and Optimization of Maleimide Based Porcupine Inhibitors

Porcupine is an O-acyltransferase that regulates Wnt secretion. Inhibiting porcupine may block the Wnt pathway which is often dysregulated in various cancers. Consequently porcupine inhibitors are thought to be promising oncology therapeutics. A high throughput screen against porcupine revealed several potent hits that were confirmed to be Wnt pathway inhibitors in secondary assays. We developed a pharmacophore model and used the putative bioactive conformation of a xanthine inhibitor for scaffold hopping. The resulting maleimide scaffold was optimized to subnanomolar potency while retaining good physical druglike properties. A preclinical development candidate was selected for which extensive in vitro and in vivo profiling is reported.

Design and synthesis of purine analogues as highly specific ligands for FcyB, a ubiquitous fungal nucleobase transporter

In the course of our study on fungal purine transporters, a number of new 3-deazapurine analogues have been rationally designed, based on the interaction of purine substrates with the Aspergillus nidulans FcyB carrier, and synthesized following an effective synthetic procedure. Certain derivatives have been found to specifically inhibit FcyB-mediated [3H]-adenine uptake. Molecular simulations have been performed, suggesting that all active compounds interact with FcyB through the formation of hydrogen bonds with Asn163, while the insertion of hydrophobic fragments at position 9 and N6 of 3-deazaadenine enhanced the inhibition.

Unexpected thermal rearrangement of N-alkoxycarbonyl imidazole acryl azides to imidazo[1,5-c]pyrimidinone or imidazo[4,5-c]pyridinone

Rearrangement of alkoxycarbonyl imidazole acryl azides in phenyl ether at 200 deg C yields imidazo[1,5-c]pyrimidinone or imidazo[1,5-c]pyridinone derivatives, depending on the size of the alkoxy substituent.