1,2,4-Triazolo[4,3-b]pyridazine

Base Information

• Chemical Name: 1,2,4-Triazolo[4,3-b]pyridazine
• CAS No.: 274-83-9
• Molecular Formula: C₅H₄N₄
• Molecular Weight: 120.114
• Hs Code.: 2933990090
• DSSTox Substance ID: DTXSID40341964
• Nikkaji Number: J101.086G
• Wikidata: Q82112473
• Mol file: 274-83-9.mol

Synonyms:1,2,4-Triazolo[4,3-b]pyridazine;[1,2,4]triazolo[4,3-b]pyridazine;274-83-9;s-Triazolo[4,3-b]pyridazine;2,3,7-Triazaindolizine;1,2,3a,4-Tetraazaindene;SCHEMBL312692;YRACHDVMKITFAZ-UHFFFAOYSA-;DTXSID40341964;MFCD22376571;AKOS015995217;A876917;J-503789

Chemical Property of 1,2,4-Triazolo[4,3-b]pyridazine

Chemical Property:

• PSA: 43.08000
• LogP: 0.12430
• Storage Temp.: 2-8°C
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 120.043596145
• Heavy Atom Count: 9
• Complexity: 105

Purity/Quality:

97% ^*data from raw suppliers

[1,2,4]Triazolo[4,3-b]pyridazine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=NN=CN2N=C1
• General Description: 1,2,4-Triazolo[4,3-b]pyridazine derivatives, including trifluoromethylated variants, are recognized for their pharmacological potential, particularly as anxiolytic and antihypertensive agents. The incorporation of a trifluoromethyl group enhances their structural uniqueness and bioactivity, making them promising candidates for further drug development. These compounds can be efficiently synthesized through strategic ring-closure reactions involving bifunctional reagents, enabling mild-condition access to novel derivatives with potential therapeutic applications.

Technology Process of 1,2,4-Triazolo[4,3-b]pyridazine

There total 3 articles about 1,2,4-Triazolo[4,3-b]pyridazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

→ [1,2,4]Triazolo[4,3-b]pyridazine (274-83-9)

Guidance literature:

With formic acid; In methanol; chloroform; water;

Reference yield: 39.0%

→ [1,2,4]Triazolo[4,3-b]pyridazine (274-83-9) + [1,2,4]triazolo[4,3-b]pyridazine-3-carboxylic acid (330440-42-1)

Guidance literature:

With phosphate buffer; immobilized α-chymotrypsin; at 25 ℃; for 72h; pH=8.0;

Reference yield: 14.0%

3-hydrazinyl pyridazine (40972-16-5) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → [1,2,4]Triazolo[4,3-b]pyridazine (274-83-9)

Guidance literature:

With Imidazole hydrochloride; at 153 ℃;

DOI:10.1016/j.tetlet.2020.151844

upstream raw materials:

3-hydrazinyl pyridazine

N,N-dimethyl-formamide

Downstream raw materials:

<1,2,4>triazolo<4,3-b>pyridazine-3-aldehyde

7,8-dihydro-s-triazolo<4,3-b>pyridazine

7-Benzyl-[1,2,4]triazolo[4,3-b]pyridazine

8-Benzyl-[1,2,4]triazolo[4,3-b]pyridazine

Refernces

Synthesis of original trifluoromethylated 6-aryl-pyridazines fused with thiazolidine or 1,2,4-triazole

10.1055/s-2005-918433

The research aims to develop an efficient synthesis of novel 8-trifluoromethyl-7H-thiazolo[3,2-b]- and 1,2,4-triazolo[4,3-b]pyridazines, which are potentially biologically active compounds. The study builds on the known pharmacological properties of 6-aryl-1,2,4-triazolo[4,3-b]pyridazine derivatives, such as their anxiolytic and antihypertensive effects, and explores the impact of incorporating a trifluoromethyl group at a unique position on these molecules. The synthesis starts from 4-trifluoromethyl-4,5-dihydropyridazin-3-one, using a five-membered ring closure strategy involving bis(electrophilic) reagents reacting with exocyclic and endocyclic nucleophilic centers on the pyridazine nucleus. Key chemicals include Lawesson’s reagent for thionation, methyl α-bromoacetate for ring closure, and various reagents like phosphorous oxy chloride and hydrazine for further functional group transformations. The study concludes that the synthesized compounds, such as 4, 8, 9, and 10a/b, can be efficiently accessed under mild conditions and are promising candidates for further biological evaluation due to their unique structure and potential for chemical transformations.