177648-99-6

Basic information

• Product Name: 3,6-Di(1H-imidazol-1-yl)pyridazine
• Synonyms: 3,6-Di(1H-imidazol-1-yl)pyridazine;3,6-Di(1H-imidazol-1-yl)pyridazine 98%;3,6-Di(1H-imidazol-1-yl)pyridazine98%
• CAS NO: 177648-99-6
• Molecular Formula: C₁₀H₈N₆
• Molecular Weight: 212.21072
• Product Categories: blocks;Heterocycles;Imidazoles
• Mol File: 177648-99-6.mol

Chemical Properties

• Boiling Point: 528.9 °C at 760 mmHg
• Flash Point: 273.7 °C
• Appearance: /
• Density: 1.42 g/cm³
• Vapor Pressure: 9.63E-11mmHg at 25°C
• Refractive Index: 1.76
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 3,6-Di(1H-imidazol-1-yl)pyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,6-Di(1H-imidazol-1-yl)pyridazine(177648-99-6)
• EPA Substance Registry System: 3,6-Di(1H-imidazol-1-yl)pyridazine(177648-99-6)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 177648-99-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3,6-Di(1H-imidazol-1-yl)pyridazine is used as a key intermediate in the synthesis of various pharmaceuticals for its presence in biologically active compounds, contributing to the development of new drugs with potential therapeutic applications.
Used in Organic Synthesis:
3,6-Di(1H-imidazol-1-yl)pyridazine is employed as a building block in organic synthesis, allowing for the creation of complex molecules with diverse applications in chemistry and materials science.
Used in Scientific Research:
3,6-Di(1H-imidazol-1-yl)pyridazine is utilized as a research tool in various scientific studies, particularly in the fields of chemistry, biology, and medicinal chemistry, to explore its properties and potential applications in drug discovery and development.

InChI:InChI=1/C10H8N6/c1-2-10(16-6-4-12-8-16)14-13-9(1)15-5-3-11-7-15/h1-8H

Upstream product

• 288-32-4 1H-imidazole 
• 141-30-0 3,6-dichlorpyridazine 

Relevant articles and documents

Syntheses and structure characterization of four inorganic-organic hybrid solids based on N-containing aromatic Brnsted bases and chlorometallates

Four organic-inorganic hybrid complexes ([(HL1)2SnCl 6]·2H2O (1) (L1=2-methylquinoline), [(HL2) 2(CdCl4)]·2H2O (2) (L2=5,7-dimethyl-1,8- naphthyridine-2-amine), [(H2L2)2SnCl6]2(Cl) (3), and [(H2L3)SnCl6]·2H2O (4) (L3=3,6-bis(imidazol-1-yl)pyridazine)) derived from N-containing aromatic Brnsted bases and metal(II) chloride dihydrate (tin(II) chloride dihydrate and cadmium(II) chloride dihydrate) were prepared and characterized by IR, X-ray structure analysis, elemental analysis, and TG analysis. The aromatic rings of the cations in all of the compounds are essentially planar. X-ray diffraction analysis revealed that 2-4 have 3-D network structures built from hydrogen bonds between the cations and chlorometallates. Water molecules also play important roles in structure extension in 1, 2, and 4. The arrangements of the anions and cations in their solid state are dominated by shape, size, and symmetry of the cations and the different structures of the chlorometallates as well as by hydrogen-bond interactions.

Metal-organic coordination architectures of bis(N-imidazolyl) pyridazine: Syntheses, structures, emission and photocatalytic properties

In efforts to explore the effects of metal ions, counter anions on the structures and properties of metal-organic complexes, seven new complexes [ZnL4(OH)2] (1), {[ZnL(AcO)2](CH3CH2OH)}∞ (2), {[ZnL(H2O)4](SO4)}∞ (3), [CdL4(OH)2] (4), {[CdL(AcO)2](CH3CH2OH)}∞ (5), {[CdL(H2O)4](SiF6)}∞ (6) and {[Cu2L2(SO4)2(H2O)2](H2O)}∞ (7) [L = 3,6-bis(N-imidazolyl) pyridazine] were synthesized and structurally characterized by elemental analyses, IR spectroscopy and single-crystal X-ray diffraction. Complexes 1 and 4 have similar mononuclear structures. Complexes 2, 3 and 6 have 1-D chain structures, while 5 reveals 2-D neutral infinite sheet structure. One 1-D chain and one 2-D sheet form complicated structure of complex 7. The ligands L adopt didentate bridging mode to coordinate to the metal ions in complexes 2, 3, and 5-7. Obviously, the structural differences among them are attributable to the differences of metal ions, counter anions and coordination modes of ligand. The fluorescent property of complexes 1-6 have been investigated and discussed. In addition, complexes 1-5 exhibit photocatalytic activity and selectivity for dye degradation under UV light.

Cobalt(II) complexes with bis(N-imidazolyl/benzimidazolyl) pyridazine: Structures, photoluminescent and photocatalytic properties

Six new CoII complexes [Co(L1)4(OH)2] (1), {[Co(L1)(H2O)4]·2ClO4}∞ (2), {[Co(L1)(H2O)4]·SiF6}∞ (3), {[Co(L1)3]·2ClO4}∞ (4), [Co(L2)Cl2]∞ (5) and {[Co(L2)2]·SiF6}∞ (6) [L1=3,6-bis(N-imidazolyl) pyridazine, L2=3,6-bis (N-benzimidazolyl) pyridazine] have been synthesized and characterized by elemental analysis, IR spectra and single crystal X-ray diffraction. Complex 1 has a mononuclear structure, while complexes 2 and 3 have 1-D chain structures. Considering the CoII centers were linked by the L1 ligands, the 3-D framework of complex 4 can be rationalized to be a {4^12.6^3} 6-c topological net with the stoichiometry uninodal net. 5 reveals a coordination 1-D zigzag chain structure consisting of a neutral chain [Co(L2)Cl2]n with the CoII centers. Complex 6 has a rhombohedral grid with a (4, 4) topology. The TGA property, fluorescent property and photocatalytic activity of complexes 1-6 have been investigated and discussed.

Discrete dinuclear and polymeric copper(I) cations bridged by 4,4′-bipyridine, trans-1,2-bis(4-pyridyl)ethene or bis(4-pyridyl) disulfide

Treatment of an acetonitrile solution of copper(I) tetrafluoroborate and 4,4′-bipyridine (4,4′-bipy) with 2-cyanoguanidine (cnge) yielded [{Cu(cnge)2}2(μ-4,4′-bipy)][BF4] 2·MeCN 1. Structural analysis revealed a planar dinuclear cation containing two, three-co-ordinate T-shaped copper centres bridged by 4,4′-bipy and terminally co-ordinated by two cnge molecules. In the absence of cnge but with an excess of copper(I), the product was [Cu(4,4′-bipy)(MeCN)2]BF4 2, structural analysis of which revealed a one-dimensional polymeric cationic zigzag chain, based on tetrahedral copper(I) atoms bridged by 4,4′-bipy and terminally co-ordinated by two MeCN molecules. The same reaction mixture but with an excess of 4,4′-bipy gave [Cu(4,4′-bipy)2]BF4·MeCN 3. The corresponding trans-1,2-bis(4-pyridyl)ethene (bpe) systems yielded the analogous [{Cu(cnge)2}2(μ-bpe)][BF4] 2·6MeCN 4, [Cu(bpe)(MeCN)2]BF4 5 and [Cu(bpe)2]BF4 6, respectively. Only one product has been isolated from the corresponding bis(4-pyridyl) disulfide (bpds) systems, [Cu(bpds)(MeCN)2]BF4 7. Attempts to produce copper(I) derivatives of 3,6-bis(imidazolyl)pyridazine (bimpydz) were unsuccessful, the copper(II) product, Cu(bimpydz)(MeCN)2(BF4)2 8, invariably being formed. Whereas the [{Cu(cnge)2}2(diimine)]2+ and [Cu(diimine)(MeCN)2]+ cations reacted with NOBF4 and NBut4NO2 forming copper(II) oxidation products, the [Cu(diimine)2]+ cations were unreactive.

Six New Complexes Based on Substituted Pyridazine Ligands: Structures and Luminescent Properties

Abstract: Three structurally related ligands 3-chloro-6-(benzoimidazol-1-yl)pyridazine (L1), 3-chloro-6-(1,2,4-triazol-1-yl)pyridazine (L2) and 3,6-bis(imidazol-1-yl)pyridazine (L3) were designed and synthesized, and six new Zn(II), Co(II), Cu(II) and Cd(II) complexes, namely, [M(L1)2Cl2] [M = Zn (1) and Co (2)], [Cu(L2)2(NO3)2(H2O)] (3), [Cu(L2)2Cl2]∞ (4), [CuL3(CH3COO)2]∞ (5) and [CdL3(SCN)2]∞ (6) were synthesized and characterized by elemental analyses, IR spectra as well as single-crystal X-ray diffraction analysis. The analysis reveals that complexes 1, 2 and 3 have a mononuclear structure, 1 and 2 have a similar structure. Complex 3 features a 1D structure with intermolecular O–H?O hydrogen bonding interactions. Complex 4 shows a 1D chain structure with bridging Clˉ ions. Complex 5 exhibits a 1D ladder structure. The 2D framework of 6 features are rectangular grid with a (4, 4) topology. Additionally, photoluminescence properties of ligands L1, L3 and complexes 1, 2 and 6 have been studied and discussed. Graphical Abstract: Six new metal-organic complexes were synthesized and structurally characterized, complexes 1, 2 and 3 have a mononuclear structure, complexes 4 and 5 show 1D chain structure, the 2D framework of 6 has a rectangle grid with a (4, 4) topology, moreover, photoluminescence properties of ligands L1, L3 and complexes 1, 2 and 6 have been studied and discussed. [Figure not available: see fulltext.].

Six complexes based on bis(imidazole/benzimidazole-1-yl)pyridazine ligands: Syntheses, structures and properties

Herein we reported six new Ni(II)/Cu(II)/Zn(II) complexes, namely, [Ni(L1)4(OH)2] (1), [Cu(L1)4(OH)2] (2), [Cu(L1)2(SiF6)]n (3), {[Cu(L2)(HCOO)2]·H2O·CH3OH}n (4), [Ni(L2)2(NO3)2]n (5) and {[Zn(L2)Cl2]·DMF}n (6) (L1 = 3,6-bis(imidazole-1-yl)pyridazine, L2 = 3,6-bis(benzimidazole-1-yl)pyridazine), which were characterized by single-crystal X-ray diffraction, elemental analysis, IR, PXRD. These complexes have been successfully constructed under interface diffusion process, heating reflux or hydrothermal conditions. The structures of 1 and 2 are mononuclear complexes. Complex 3 exhibits a 6-connected 3D topology network with the Schl?fli symbol of (412·63). In complex 4, two Cu(II) were connected through two HCOO? anions to form dinuclear structure unit, which is arranged into a 1D ladder-like structure by μ2-L2 ligands. Complexes 5 and 6 are 1D zigzag chains connected by L2 ligands, but the Ni(II) ion is six-coordinated in 5 and the Zn(II) ion is four-coordinated in 6. Moreover, the solid-state luminescence property and UV–vis diffuse reflection spectrum of complex 6 have been investigated and discussed.

Synthesis, antibacterial and antioxidant properties of pyrazolylpyridazines

A number of 6-chloro-3-(pyrazol-1′-yl) pyridazines were prepared from 3,6-dichloropyridazine via either reaction with hydrazine followed I by reaction with appropriate reagents to develop the pyrazole or through a nucleophilic reaction with a pyrazole. So

Pyridazine-based N-heterocyclic carbene complexes and ruthenium-catalyzed oxidation reaction of alkenes

[Ru2Cl(L)(CH3CN)4](PF6) 3 (1, L = 3,6-bis(N-(pyridylmethyl)imidazolylidenyl)pyridazine), [Cu3La3](PF6)3 (2, L a = 3-(N-(pyridylmethyl)imidazolylidenyl)-6-(N-(pyridylmethyl) imidazolylonyl)pyridazine), [Pd2(allyl)2L](PF 6)2 (3), [Pd2(allyl)2L b2](PF6)2 (4, Lb = N-pyridylmethylimidazole), and [NiLc2](PF 6)2 (5, Lc = 3-(N-(pyridylmethyl) imidazolylidenyl)-6-methoxylpyridazine) have been synthesized and fully characterized by NMR spectroscopy, elemental analysis, and X-ray diffraction analysis. In complex 1, ligand L binds to two Ru(II) centers, forming a well-behaved Ru2(L)Cl plane with a five-membered metallocyclic ring. Complex 2 is trinuclear, containing a triangular Cu3 unit bonded together by three 3-(N-(pyridylmethyl)imidazolylidenyl)-6-(N-(pyridylmethyl) imidazolylonyl)pyridazine, where one imidazolylidene was oxidized into imidazolone. Deprotonation reaction with Ag2O in CH3CN and CH3OH resulted in C-N cleavage of the imidazolium salt, and subsequent reaction with [Pd(allyl)Cl]2 and Ni(PPh3) 2Cl2 gave 4 and 5, respectively. Dinuclear Ru(II)-NHC complex 1 exhibits excellent catalytic activity for the oxidation of alkenes into diketones.

Synthesis and antihypertensive activity of new 6-heteroaryl-3-hydrazinopyridazine derivatives

The synthesis and pharmacological activity of new 6-heteroaryl-3-hydrazinopyridazines with antihypertensive action are described. The introduction of pyrrole, pyrazole, imidazole, triazole, tetrazole, thiophene, indole, and carbazole heterocyclic rings into the 6 position of the pyridazine nucleus has been carried out by three different methods of synthesis. The hypotensive action has been examined on normotensive and spontaneously hypertensive rats by comparison with dihydralazine (I). 6-Imidazol-1-yl derivatives have proved particularly active. Of these derivatives 3-hydrazino-6-(2-methylimidazol-1-yl)pyridazine (7c) achieves 4.9 times the activity of dihydralazine when administered orally to spontaneously hypertensive rats. The LD50 values of 7c and dihydralazine are very similar.