41227-72-9

Basic information

• Product Name: 3-(Chloromethyl)pyridazine
• Synonyms: 3-(Chloromethyl)pyridazine;3-(Chloromethyl)pyridazin...;Pyridazine, 3-(chloroMethyl)-
• CAS NO: 41227-72-9
• Molecular Formula: C₅H₅ClN₂
• Molecular Weight: 128.5596
• Mol File: 41227-72-9.mol

Chemical Properties

• Boiling Point: 282.3 °C at 760 mmHg
• Flash Point: 151.6 °C
• Appearance: /
• Density: 1.241 g/cm³
• Vapor Pressure: 0.00577mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 2.12±0.10(Predicted)
• CAS DataBase Reference: 3-(Chloromethyl)pyridazine(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(Chloromethyl)pyridazine(41227-72-9)
• EPA Substance Registry System: 3-(Chloromethyl)pyridazine(41227-72-9)

Safety Data

• Hazardous Substances Data: 41227-72-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
3-(Chloromethyl)pyridazine is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to facilitate the creation of new drug molecules with potential therapeutic properties. Its reactivity allows for the attachment of different functional groups, enhancing the pharmacological activity of the resulting compounds.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(Chloromethyl)pyridazine is utilized as an intermediate in the production of agrochemicals, contributing to the development of effective pesticides and other agricultural chemicals. Its role in these applications is to provide a stable and reactive platform for the attachment of functional groups that can target specific pests or enhance crop protection.
Used in Organic Synthesis:
3-(Chloromethyl)pyridazine is employed as a building block in organic synthesis, where it is used to construct complex organic molecules with diverse applications. Its chloromethyl group offers a reactive site for further functionalization, making it a valuable component in the synthesis of various organic compounds.
Used in Chemical Research:
As a reagent in chemical research, 3-(Chloromethyl)pyridazine is used to explore new chemical reactions and mechanisms. Its unique structure and reactivity make it an interesting subject for studies aimed at understanding and optimizing synthetic pathways and developing new methodologies in chemistry.
Note: The information provided is based on chemical data and does not promote the use or consumption of the chemicals mentioned.

InChI:InChI=1/C5H5ClN2/c6-4-5-2-1-3-7-8-5/h1-3H,4H2

Upstream product

• 1632-76-4 3-methylpyridazine 
• 87-90-1 trichloroisocyanuric acid 
• 1126-10-9 ethyl 3-pyridazinecarboxylate 
• 37444-46-5 3-hydroxymethylpyridazine 
• 2164-61-6 pyridazine-3-carboxylic acid 

Downstream Products

• 497853-55-1 4-{[(3-pyridazinyl)methyl]sulfanyl}aniline 
• 497852-16-1 7-{4-[2-(butoxy)ethoxy]phenyl}-1-isobutyl-N-({4-[(3-pyridazinyl)methyl]sulfanyl}phenyl)-2,3-dihydro-1H-1-benzazepine-4-carboxamide 
• 1008518-76-0 1-[2-(4-hydroxymethyl-phenyl)-ethyl]-4-(pyridazin-3-ylmethoxy)-1H-pyridin-2-one 

Relevant articles and documents

NOVEL TETRAZOLE COMPOUNDS AND THEIR USE IN THE TREATMENT OF TUBERCULOSIS

The invention relates to a compound of Formula (I) or a pharmaceutically acceptable salt thereof and their use in therapy, for example in the treatment of mycobacterial infections or in the treatment of diseases caused by mycobacterium, such as tuberculosis.

ATG7 INHIBITORS AND THE USES THEREOF

Disclosed are chemical entities which are compounds of formula (I) : or a pharmaceutically acceptable salt thereof, wherein R1, R2, and Ra have the values described herein. Chemical entities according to the disclosure can be useful as inhibitors of ATG7. Further provided are pharmaceutical compositions comprising a chemical entity of the disclosure and methods of using the compositions in the treatment of cancer.

Synthesis and characterization of nitrogen-rich macrocyclic ligands and an investigation of their coordination chemistry with lanthanum(III)

Derivatives of the ligand 1,4,7,10-tetraazacyclododecane (cyclen) containing pendant N-heterocyclic donors were prepared. The heterocycles pyridine, pyridazine, pyrimidine, and pyrazine were conjugated to cyclen to give 1,4,7,10-tetrakis(pyridin-2-ylmethyl)-1,4,7,10-tetraazacyclododecane (Lpy), 1,4,7,10-tetrakis(3-pyridazylmethyl)-1,4,7,10-tetraazacyclododecane (Lpyd), 1,4,7,10-tetrakis(4-pyrimidylmethyl)-1,4,7,10-tetraazacyclododecane (Lpyr), and 1,4,7,10-tetrakis(2-pyrazinylmethyl)-1,4,7,10-tetraazacyclododecane (Lpz), respectively. The coordination chemistry of these ligands was explored using the La3+ ion. Accordingly, complexes of the general formula [La(L)(OTf)](OTf)2, where OTf = trifluoromethanesulfonate and L = Lpy (1), Lpyd (2), Lpyr (3), and Lpz (4), were synthesized and characterized by NMR spectroscopy. Crystal structures of 1 and 2 were also determined by X-ray diffraction studies, which revealed 9-coordinate capped, twisted square-antiprismatic coordination geometries for the central La3+ ion. The conformational dynamics of 1-4 in solution were investigated by variable-temperature NMR spectroscopy. Dynamic line-shape and Eyring analyses enabled the determination of the activation parameters for the interconversion of enantiomeric forms of the complexes. Unexpectedly, the different pendant N-heterocycles of 1-4 give rise to varying values for the enthalpies and entropies of activation for this process. Density functional theory calculations were carried out to investigate the mechanism of this enantiomeric interconversion. Computed activation parameters were consistent with those experimentally determined for 1 but differed somewhat from those of 2-4.

Bispidine platform grants full control over magnetic state of ferrous chelates in water

A bicyclic ligand platform for iron(II), which allows total control over the complex's magnetic properties in aqueous solution simply by varying one of the six coordination sites of the bispidine ligand, is reported. To achieve this, an efficient synthetic route to an N5 bispidine framework (ligand L4) that features an unsubstituted N-7 site is established. Then, by choosing appropriate N-7-coordinating substituents, the spin state of choice can be imposed on the corresponding ferrous complexes under environmentally relevant conditions in water and near-room temperature. Importantly, the first low-spin and diamagnetic iron(II) chelates in the bispidine series, both in the solid state and in aqueous solution, are reported. The eradication of head-on steric clashes between pendent coordinating arms is at the origin of this success. A new pair of constitutionally similar ferrous coordination compounds of a multidentate ligand system is obtained, which exhibits a distinctly binary (off-on) magnetic relationship. The new synthetic intermediate L4 may be substituted in just one step by any desired pendent arm, thus allowing access to complexes with finely tuned magnetic properties. All under control: Structural variation of bispidines allows for the preparation of ferrous complexes that adopt magnetic properties of choice under environmentally benign conditions in water at room temperature. Pairs of constitutionally similar, robust chelates with a binary off-on magnetic relationship are obtained (see figure). Copyright

HYDRAZONE COMPOUNDS AND THEIR USE

The present invention relates to hydrazone compounds of Formula I: (I) and pharmaceutically acceptable salts and stereoisomers thereof, wherein R1, R2, R3, R4, L1, and L2 are defined as set forth in the specification. The invention is also directed to the use of compounds of Formula I as inhibitors of TRPM5 protein.

TETRACYCLIC INDOLE DERIVATIVES AS ANTIVIRAL AGENTS

The present invention relates to tetracyclic indole derivatives of formula (I); wherein Ar, D1, D2, D3, D4, W, X, Y and Z are defined herein, and pharmaceutically acceptable salts thereof, pharmaceutical composi

Discovery of functionally selective 7,8,9,10-tetrahydro-7,10-ethano-1,2,4- triazolo[3,4-a]phthalazines as GABAA receptor agonists at the α3 subunit

We have previously identified the 7,8,9,10-tetrahydro-7,10-ethano-1,2,4- triazolo[3,4-a]phthalazine (1) as a potent partial agonist for the 0.3 receptor subtype with 5-fold selectivity in binding affinity over α1. This paper describes a detailed investigation of the substituents on this core structure at both the 3- and 6-positions. Despite evaluating a wide range of groups, the maximum selectivity that could be achieved in terms of affinity for the α3 subtype over the α1 subtype was 12-fold (for 57). Although most analogues showed no selectivity in terms of efficacy, some did show partial agonism at α1 and antagonism at α3 (e.g., 25 and 75). However, two analogues tested (93 and 96), both with triazole substituents in the 6-position, showed significantly higher efficacy for the α3 subtype over the α1 subtype. This was the first indication that selectivity in efficacy in the required direction could be achieved in this series.

3-Phenyl-6-(2-pyridyl)methyloxy-1,2,4-triazolo[3,4-a]phthalazines and Analogues: High-Affinity γ-Aminobutyric Acid-A Benzodiazepine Receptor Ligands with α2, α3, and α5-Subtype Binding Selectivity over α1

Studies with our screening lead 5 and the literature compound 6 led to the identification of 6-benzyloxy-3-(4-methoxy)phenyl-1,2,4-triazolo[3,4-a]phthalazine 8 as a ligand with binding selectivity for the γ-aminobutyric acid-A (GABA-A) α3- and α5-containing receptor subtypes over the GABA-A α1 subtype (Ki: α2 = 850 nM, α3 = 170 nM, α5 = 72 nM, α1 = 1400 nM). Early optimization studies identified the close analogue 10 (Ki: α2 = 16 nM, α3 = 41 nM, α5 = 38 nM, α1 = 280 nM) as a suitable lead for further study. High-affinity ligands were identified by replacing the 6-benzyloxy group of compound 10 with 2-pyridylmethoxy (compound 29), but binding selectivity was not enhanced (K i: α2 = 1.7 nM, α3 = 0.71 nM, α5 = 0.33 nM, α1 = 2.7 nM). Furthermore, on evaluation in xenopus oocytes, 29 was discovered to be a weak to moderate inverse agonist at all four receptor subtypes α1, -7%; α2, -5%; α3, -16%; α5, -5%). Replacement of the 3-phenyl group of 29 with alternatives led to reduced affinity, and smaller 3-substituents led to reduced efficacy. Methyl substitution of the benzo-fused ring of 29 at the 7-, 8-, and 10-positions resulted in increased efficacy although selectivity was abolished. Increased efficacy and retention of selectivity for α3 over α1 was achieved with the 7,8,9,10-tetrahydro-(7,10-ethano)-phthalazine 62. Compound 62 is currently one of the most binding selective GABA-A α3-benzodiazepine-site partial agonists known, and although its selectivity is limited, its good pharmacokinetic profile in the rat (33% oral bioavailability after a 3 mg/kg dose, reaching a peak plasma concentration of 179 ng/mL; half-life of 1 h) made it a useful pharmacological tool to explore the effect of a GABA-A α2/α3 agonist in vivo.

Pyrazolo-triazine derivatives as ligands for GABA receptors

Compounds according to Formula (I): or a salt or prodrug thereof, have good affinity as ligands for the alpha2 and/or alpha3 subunit of the human GABAAreceptor and are useful for treatment of disorders of the central nervous system, including a

Substituted 1,2,4-triazolo[3,4-a]phthalazine derivatives as GABA alpha 5 ligands

Substituted 1,2,4-Triazolo[3,4-A]phthalazine derivatives are GABA Alpha 5 ligands and are represented by the formula