17973-86-3

Usage

Uses

Used in Pharmaceutical Industry:
3,6-Dibromopyridazide is used as a pharmaceutical intermediate for the development of new drugs and medications. Its chemical properties allow it to be a key component in the synthesis of various pharmaceutical compounds, contributing to the advancement of medical treatments.
Used in Organic Synthesis:
In the field of organic synthesis, 3,6-dibromopyridazide is utilized as a building block for the creation of complex organic molecules. Its reactivity and structural features make it an essential component in the synthesis of a wide array of organic compounds.
Used in Organic Solvents:
3,6-Dibromopyridazide is also employed as a component in the formulation of organic solvents. Its properties enable it to improve the performance and characteristics of solvents used in various applications, including industrial processes and chemical reactions.
Used in Dye Production:
In the dye industry, 3,6-dibromopyridazide is used as a key intermediate for the production of various dyes. Its chemical properties allow it to contribute to the development of dyes with specific color characteristics and performance attributes.
Used in Pesticide Production:
3,6-Dibromopyridazide plays a role in the synthesis of pesticides, where it is used as an intermediate to create effective and targeted pest control agents. Its chemical properties make it a valuable component in the development of new and improved pesticides.
Used in Perfumery:
In the perfumery industry, 3,6-dibromopyridazide is used as an intermediate for the creation of unique and complex fragrances. Its chemical structure allows it to contribute to the development of scents with specific olfactory properties and characteristics.

Preparation

3,6-dibromopyridazine for Synthesis: A mixture of maleic hydrazide (1.1 g, 10 mmol) and PBr5 (4.7 g, 11 mmol) was heated at 100 °C until no more white fumes of hydrogen bromide were produced (~2 h). After cooling, the orange residue was poured into ice water and the resulting mixture was extracted with CH2Cl2 (3 x 20 mL). The organic layer was washed with saturated aqueous NaHCO3, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography on silica gel (CH2Cl2) to give 3,6-dibromopyridazine as a white solid (1.20 g, 50%).

InChI:InChI=1/C4H2Br2N2/c5-3-1-2-4(6)8-7-3/h1-2H

Upstream product

• 502-95-4 tetrahydropyridazine-3,6-dione 
• 123-33-1 Maleic hydrazide 
• 123-33-1 3,6-dihydroxypyridazine 
• 204254-06-8 3,6-bis(4-pyridyl)-1,2-diazine 
• 1692-15-5 4-pyridylboronic acid 
• 71-43-2 benzene 
• 935-04-6 benzyl vinyl ether 
• 1071030-18-6 3,6-dibromo-1,2,4,5-tetrazine 
• 75-20-7 calcium carbide 

Downstream Products

• 17321-29-8 3-metossi-6-bromopiridazina 
• 91445-78-2 4-amino-N-(6-bromo-pyridazin-3-yl)-benzenesulfonamide 
• 88497-27-2 6-bromopyridazin-3-amine 
• 695184-05-5 4-(6-bromo-pyridazin-3-yl)-1, 4-diazabicyclo [3.2. 2] nonane 
• 103829-12-5 4-(6-bromo-3-pyridazinyloxy)-3-nitroaniline 
• 927673-86-7 4-(6-bromopyridazin-3-yl)morpholine 
• 135034-10-5 3-chloro-6-iodopyridazine 
• 1036226-83-1 3-bromo-6-(2-fluoro-phenyl)-pyridazine 
• 1159250-88-0 3-bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine 
• 1276656-59-7 2-{6-[2-amino-5-(trifluoromethyl)phenyl]pyridazin-3-yl}-4-(trifluoromethyl)aniline 
• 1361392-14-4 3-(4-(benzyloxy)cyclohexyloxy)-6-bromopyridazine 
• 1416806-29-5 C₁₅H₁₁F₅N₂O₂ 
• 1215072-74-4 C₁₁H₆BrF₃N₂ 
• 1424016-57-8 (3,6-dibromopyridazin-4-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Donor-acceptor-donor-type liquid crystal with a pyridazine core

(Chemical Equation Presented) A new liquid crystalline material having an ethylenedioxythiophene-pyridazine-ethylenedioxythiophene (EDOT-PDZ-EDOT) core with two peripheral long alkyl chains was prepared. The designated donor-acceptor-donor (D-A-D)-type core structure induced a distinct smectic liquid crystalline phase due to the strong intermolecular interaction. The photophysical property and the layer structure of the liquid crystal were investigated by differential scanning calorimetry, polarized light microscopy, X-ray diffraction, and cyclic voltammetry.

Pyridazine N-Oxides as Photoactivatable Surrogates for Reactive Oxygen Species

A method for the photoinduced evolution of atomic oxygen from pyridazine N-oxides was developed. This underexplored oxygen allotrope mediates arene C-H oxidation within complex, polyfunctional molecules. A water-soluble pyridazine N-oxide was also developed and shown to promote photoinduced DNA cleavage in aqueous solution. Taken together, these studies highlight the utility of pyridazine N-oxides as photoactivatable O(3P) precursors for applications in organic synthesis and chemical biology.

One-Pot and Two-Chamber Methodologies for Using Acetylene Surrogates in the Synthesis of Pyridazines and Their D-Labeled Derivatives

Acetylene surrogates are efficient tools in modern organic chemistry with largely unexplored potential in the construction of heterocyclic cores. Two novel synthetic paths to 3,6-disubstituted pyridazines were proposed using readily available acetylene surrogates through flexible C2 unit installation procedures in a common reaction space mode (one-pot) and distributed reaction space mode (two-chamber): (1) an interaction of 1,2,4,5-tetrazine and its acceptor-functionalized derivatives with a CaC2?H2O mixture performed in a two-chamber reactor led to the corresponding pyridazines in quantitative yields; (2) [4+2] cycloaddition of 1,2,4,5-tetrazines to benzyl vinyl ether can be considered a universal synthetic path to a wide range of pyridazines. Replacing water with D2O and vinyl ether with its trideuterated analog in the developed procedures, a range of 4,5-dideuteropyridazines of 95–99% deuteration degree was synthesized for the first time. Quantum chemical modeling allowed to quantify the substituent effect in both synthetic pathways.

The difference in the CO2adsorption capacities of different functionalized pillar-layered metal-organic frameworks (MOFs)

The excessive use of fossil energy has caused the CO2concentration in the atmosphere to increase year by year. MOFs are ideal CO2adsorbents that can be used in CO2capture due to their excellent characteristics. Studies of the structure-activity relationship between the small structural differences in MOFs and the CO2adsorption capacities are helpful for the development of efficient MOF-based CO2adsorbents. Therefore, a series of pillar-layered MOFs with similar structural and different functional groups were designed and synthesized. The CO2adsorption tests were carried out at 273 K to explore the relationship between the small structural differences in MOFs caused by different functional groups and the CO2adsorption capacities. Significantly, compound6which contains a pyridazinyl group has a 30.9% increase in CO2adsorption capacity compared to compound1with no functionalized group.

Self-assembly of 3,6-bis(4-triazolyl)pyridazine ligands with copper(I) and silver(I) ions: Time-dependant 2D-NOESY and ultracentrifuge measurements

Two 3,6-bis(R-1H-1,2,3-triazol-4-yl)pyridazines (R=mesityl, monodisperse (CH2-CH2O)12CH3) were synthesized by the copper(I)-catalyzed azide-alkyne cycloaddition and self-assembled with tetrakis(acetonitrile)copp

Substituted pyridazines and fused pyridazines with angiogenesis inhibiting activity

Substituted and Fused pyridazines having angiogenesis inhibiting activity and the generalized structural formula wherein the ring containing A, B, D, E, and L is a nitrogen-containing heterocycle; groups X and Y may be any of a variety of defined linking units; R1 and R2 may be defined independent substituents or together may be a ring-defining bridge; ring J may be an aryl, pyridyl, or cycloalkyl group; and G groups may be any of a variety of defined substituents. Pharmaceutical compositions containing these materials, and methods of treating a mammal having a condition characterized by abnormal angiogenesis or hyperpermiability processes using these materials are also disclosed.

SUBSTITUTED (AMINOIMINOMETHYL OR AMINOMETHYL) BENZOHETEROARYL COMPOUNDS

This invention is directed to an (aminoiminomethyl or aminomethyl) benzoheteroaryl compound of formula I which is useful for inhibiting the activity of Factor Xa by combining said compound with a composition containing Factor Xa. The present invention is also directed to compositions containing compounds of the formula I, methods for their preparation, their use, such as in inhibiting the formation of thrombin or for treating a patient suffering from, or subject to, a disease state associated with a physiologically detrimental excess amount of thrombin.

Fungicidal pyridazines

Plants are protected from the damaging effects of Phycomycetous fungi by a series of pyridazines of formula STR1 wherein R3 is chloro, bromo, methyl, cyano or iodo; R is chloro, bromo, iodo, methyl, cyano or furan-2-ylmethoxy; R1 is