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4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one, commonly referred to as TBTU, is a versatile chemical compound that serves as a coupling reagent in the field of peptide synthesis. This white to off-white crystalline solid is highly soluble in organic solvents such as dimethylformamide and dimethyl sulfoxide. TBTU is renowned for its high reactivity, efficiency in amidation and esterification reactions, and its low racemization rates, which make it a preferred choice for synthesizing peptides and other complex organic molecules. Its non-toxic nature and ease of handling further enhance its appeal in chemical synthesis.

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  • 3243-24-1 Structure
  • Basic information

    1. Product Name: 4,7,9-Triazabicyclo[4.3.0]nona-2,7,10-trien-5-one
    2. 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
    3. CAS NO:3243-24-1
    4. Molecular Formula: C6H5N3O
    5. Molecular Weight: 133.10752
    6. EINECS: N/A
    7. Product Categories: N/A
    8. Mol File: 3243-24-1.mol
  • Chemical Properties

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

    1. Hazard Codes: N/A
    2. Statements: N/A
    3. Safety Statements: N/A
    4. WGK Germany:
    5. RTECS:
    6. HazardClass: N/A
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 3243-24-1(Hazardous Substances Data)

3243-24-1 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.

Check Digit Verification of cas no

The CAS Registry Mumber 3243-24-1 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,4 and 3 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3243-24:
(6*3)+(5*2)+(4*4)+(3*3)+(2*2)+(1*4)=61
61 % 10 = 1
So 3243-24-1 is a valid CAS Registry Number.
InChI:InChI=1/C6H5N3O/c10-6-5-4(1-2-7-6)8-3-9-5/h1-3H,(H,7,10)(H,8,9)

3243-24-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name 1H-Imidazo[4,5-c]pyridin-4-ol

1.2 Other means of identification

Product number -
Other names imidazo<4,5-c>pyridin-4-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:3243-24-1 SDS

3243-24-1Relevant articles and documents

Scaffold Hopping and Optimization of Maleimide Based Porcupine Inhibitors

Ho, Soo Yei,Alam, Jenefer,Jeyaraj, Duraiswamy Athisayamani,Wang, Weiling,Lin, Grace Ruiting,Ang, Shi Hua,Tan, Eldwin Sum Wai,Lee, May Ann,Ke, Zhiyuan,Madan, Babita,Virshup, David M.,Ding, Li Jun,Manoharan, Vithya,Chew, Yun Shan,Low, Choon Bing,Pendharkar, Vishal,Sangthongpitag, Kanda,Hill, Jeffrey,Keller, Thomas H.,Poulsen, Anders

, p. 6678 - 6692 (2017/08/18)

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

Lougiakis, Nikolaos,Gavriil, Efthymios-Spyridon,Kairis, Markelos,Sioupouli, Georgia,Lambrinidis, George,Benaki, Dimitra,Krypotou, Emilia,Mikros, Emmanuel,Marakos, Panagiotis,Pouli, Nicole,Diallinas, George

, p. 5941 - 5952 (2016/11/09)

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

Jiao, Yuguo,Valente, Edward,Garner, Solomon T.,Wang, Xiaotang,Yu, Hongtao

, p. 5879 - 5882 (2007/10/03)

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.

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