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
• Article Data: 3

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

General Description

4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one, also known as TBTU, is a chemical compound commonly used as a coupling reagent in peptide synthesis. It is a white to off-white crystalline solid that is highly soluble in organic solvents such as dimethylformamide and dimethyl sulfoxide. TBTU is a powerful and efficient reagent for amidation and esterification reactions, and it is often used in combination with N,N-diisopropylethylamine as a base. It is known for its high reactivity and low racemization rates, making it a popular choice for the synthesis of peptides and other complex organic molecules. TBTU is also non-toxic and relatively easy to handle, further adding to its appeal in chemical synthesis.

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

• 33631-02-6 3,4-diamino-pyridin-2-ol 
• 2770-01-6 4-chloro-1H-imidazo[4,5-c]pyridine 
• 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 

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.

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.