26452-80-2

Basic information

• Product Name: 2,4-Dichloropyridine
• Synonyms: 2,4-Dichloropyridine,97%;2,4-Dichloropyridine ,98%;Pyridine, 2,4-dichloro-;2,4-Dichloropyridine 97%;2,4-DICHLOROPYRIDINE;IFLAB-BB F2108-0071;2,4-Dichlorpyridine
• CAS NO: 26452-80-2
• Molecular Formula: C₅H₃Cl₂N
• Molecular Weight: 147.99
• EINECS: 247-717-7
• Product Categories: blocks;Pyridines;Pyridine;pyridine derivative;Pyridine Series;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridines derivates;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Chlorinated heterocyclic series;Aromatics;Miscellaneous Reagents
• Mol File: 26452-80-2.mol

Chemical Properties

• Melting Point: -1 °C
• Boiling Point: 189-190 °C(lit.)
• Flash Point: 189-190°C
• Appearance: Light yellow liquid
• Density: 1.37
• Vapor Pressure: 0.658mmHg at 25°C
• Refractive Index: 1.55-1.554
• Storage Temp.: Refrigerator
• Solubility: Chloroform
• PKA: 0.12±0.10(Predicted)
• BRN: 108666
• CAS DataBase Reference: 2,4-Dichloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dichloropyridine(26452-80-2)
• EPA Substance Registry System: 2,4-Dichloropyridine(26452-80-2)

Safety Data

• Hazard Codes: T,Xi,Xn
• Statements: 25-38-41-43-36/37/38-20/22
• Safety Statements: 26-36/37/39-45-36
• RIDADR: 2810
• WGK Germany: 3
• RTECS: NC3410400
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 26452-80-2(Hazardous Substances Data)

Usage

Uses

Used in the Preparation of Host Materials for Light-Emitting Diodes (LEDs):
2,4-Dichloropyridine is used as a reactant for synthesizing host materials with heterocyclic cores, which are essential components in the fabrication of light-emitting diodes. These materials contribute to the efficiency and performance of LEDs, making them suitable for various applications such as displays, lighting, and signaling.
Used in the Preparation of Sulfonylated Pyridines:
In the chemical industry, 2,4-Dichloropyridine serves as a precursor for the synthesis of sulfonylated pyridines. These compounds are valuable intermediates in the production of pharmaceuticals, agrochemicals, and other specialty chemicals, due to their unique reactivity and functional group compatibility.
Used in the Preparation of Pyrazine and Quinoline:
2,4-Dichloropyridine is also utilized in the synthesis of pyrazine and quinoline derivatives through aromatic nucleophilic substitution of azines with sodium sulfinates. These heterocyclic compounds find applications in various fields, including pharmaceuticals, dyes, and materials science, owing to their diverse chemical properties and potential for further functionalization.

InChI:InChI=1/C5H3Cl2N/c6-4-1-2-8-5(7)3-4/h1-3H

Upstream product

• 19798-80-2 2-Amino-4-chloropyridine 
• 626-03-9 3-deazauracil 
• 14432-12-3 4-Amino-2-chloropyridine 
• 1124-33-0 4-nitraminopyridine N-oxide 
• 856956-19-9 1-methyl-1H-pyridine-2,4-dione 
• 10026-13-8 phosphorus pentachloride 
• 7791-25-5 sulfuryl dichloride 
• 626-61-9 4-Chloropyridine 
• 153034-86-7 2-chloro-4-iodopyridine 
• 1984-23-2 p-nitrophenyl isocyanide 
• 837365-03-4 2,4-dichloro-6-hydrazinopyridine 
• 837365-00-1 2,4,6-trichloro-3-(trimethylsilyl)pyridine 
• 16063-69-7 2,4,6-trichloropyridine 
• 98027-84-0 2,6-dichloro-4-iodopyridine 

Downstream Products

• 18677-43-5 2,4-dimethoxypyridine 
• 52311-30-5 2,4-Diethoxypyridin 
• 19798-80-2 2-Amino-4-chloropyridine 
• 14432-12-3 4-Amino-2-chloropyridine 
• 134031-24-6 2,4-dichloro-3-pyridine Carboxaldehyde 
• 71506-85-9 2,4-bis-methylthiopyridine 
• 83674-71-9 2,4-diiodo-pyridine 
• 110-86-1 pyridine 
• 262423-77-8 2,4-dichloronicotinic acid 
• 343781-36-2 2,4-dichloro-3-iodo-pyridine 
• 58530-53-3 2,4-dibromopyridine 
• 68157-60-8 N-(2-chloro-4-pyridyl)-N'-phenylurea 
• 59047-70-0 2-chloro-N,N-dimethylpyridin-4-amine 
• 628323-61-5 2-(4-chloropyridin-2-yl)-5-fluorobenzonitrile 

Relevant articles and documents

Deaminative chlorination of aminoheterocycles

Selective modification of heteroatom-containing aromatic structures is in high demand as it permits rapid evaluation of molecular complexity in advanced intermediates. Inspired by the selectivity of deaminases in nature, herein we present a simple methodology that enables the NH2 groups in aminoheterocycles to be conceived as masked modification handles. With the aid of a simple pyrylium reagent and a cheap chloride source, C(sp2)?NH2 can be converted into C(sp2)?Cl bonds. The method is characterized by its wide functional group tolerance and substrate scope, allowing the modification of >20 different classes of heteroaromatic motifs (five- and six-membered heterocycles), bearing numerous sensitive motifs. The facile conversion of NH2 into Cl in a late-stage fashion enables practitioners to apply Sandmeyer- and Vilsmeier-type transforms without the burden of explosive and unsafe diazonium salts, stoichiometric transition metals or highly oxidizing and unselective chlorinating agents. [Figure not available: see fulltext.]

Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

A convenient and efficient method for the synthesis of 2-halogen-substituted pyridines is described. The decarboxylative halogenation of 2-picolinic acids with dihalomethane proceeded smoothly via N-chlorocarbene intermediates to afford 2-halogen-substituted pyridines in satisfactory to excellent yields under transition-metal-free conditions. This new type of decarboxylative halogenation is operationally simple and exhibits high functional-group tolerance.

Small molecule inhibitors of anthrax edema factor

Anthrax is a highly lethal disease caused by the Gram-(+) bacteria Bacillus anthracis. Edema toxin (ET) is a major contributor to the pathogenesis of disease in humans exposed to B. anthracis. ET is a bipartite toxin composed of two proteins secreted by the vegetative bacteria, edema factor (EF) and protective antigen (PA). Our work towards identifying a small molecule inhibitor of anthrax edema factor is the subject of this letter. First we demonstrate that the small molecule probe 5′-Fluorosulfonylbenzoyl 5′-adenosine (FSBA) reacts irreversibly with EF and blocks enzymatic activity. We then show that the adenosine portion of FSBA can be replaced to provide more drug-like molecules which are up to 1000-fold more potent against EF relative to FSBA, display low cross reactivity when tested against a panel of kinases, and are nanomolar inhibitors of EF in a cell-based assay of cAMP production.

Concise Entries to 4-Halo-2-pyridones and 3-Bromo-4-halo-2-pyridones

Methods for the synthesis of both simple 4-halo-2-pyridones and more functionalized 3,4-di- and (3,4,5-tri)-halo-2-pyridones are described that are based on a combination of Sandmeyer and regioselective (copper-mediated) halogenation, with a 2-chloro or a 2-benzyloxy moiety serving as a masked 2-pyridone.

Dehalogenation degradation method for halogenated pyridine compound

The invention provides a dehalogenation degradation method for a halogenated pyridine compound. The halogenated pyridine compound is adopted as a raw material, alcohol is adopted as a hydrogen source, water is adopted as a solvent, reacting is carried out for 3-10 h under normal pressure at the temperature of 20 DEG C to 120 DEG C under the action of a supported catalyst, and the halogenated pyridine compound is subjected to dehalogenation degradation in situ through water phase hydrogen production. A pyridine ring of the halogenated pyridine compound at least contains an F or Cl or Br or I substituent group. The supported catalyst is composed of an active component and a carrier, the active component is composed of a mixture of transition metal and other metal, the transition metal is one of Rh, Pd, Pt and Ni, and other metal is one of Se, Ca, Ba, La and Ce. The carrier is one of activated carbon, kieselguhr, zeolite, gamma-Al2O3, AlF3 and MgO. H2 is not directly used as a reduction agent, activated hydrogen is prepared through in-situ catalysis to directly participate in reacting, the advantages of being high in reaction activity, high in selectivity, high in safety, environmentally friendly and the like are achieved, and good application prospects are achieved.

A general approach to (trifluoromethoxy)pyridines: First X-ray structure determinations and quantum chemistry studies

The previously unknown 2-, 3-, and 4-(trifluoromethoxy)pyridines have now become readily accessible by means of an efficient and straightforward large-scale synthesis. Their regioselective functionalization by organometallic methods has been studied and has afforded new and highly important building blocks for life-sciences-oriented research. In addition, the first X-ray crystallographic structure determinations of (trifluoromethoxy)pyridines have been performed. Lowest-energy conformations of (trifluoromethoxy)pyridines and (trifluoromethoxy)pyridinium cations were determined by in silico studies. A general and efficient route to (trifluoromethoxy)pyridines is reported. Regioselective functionalization by organometallic methods afforded new and highly important building blocks for life-sciences-oriented research. The first X-ray crystallographic structure determinations of (trifluoromethoxy)pyridines have been performed and supported by in silico studies.

CHEMICAL COMPOUNDS AND PROCESSES

The present invention relates generally to chemical compounds and methods for their use and preparation. In particular, the invention relates to chemical compounds which may possess useful therapeutic activity, use of these compounds in methods of therapy and the manufacture of medicaments as well as compositions containing these compounds.

PYRIDINE DERIVATIVES AND THEIR USE AS MEDICAMENTS FOR TREATING DISEASES RELATED TO MCH RECEPTOR

The present invention encompasses novel substituted pyridine compounds of Formula (I), which act as MCH receptor antagonists. These compositions and pharmaceutical compositions thereof are useful in the prophylaxis or treatment of improving memory function, sleeping and arousal, anxiety, depression, mood disorders, seizure, obesity, diabetes, appetite and eating disorders, cardiovascular disease, hypertension, dyslipidemia, myocardial infarction, binge eating disorders including bulimia, anorexia, mental disorders including manic depression, schizophrenia, delirium, dementia, stress, cognitive disorders, attention deficit disorder, substance abuse disorders and dyskinesias including Parkinson's disease, epilepsy, and addiction.

Regiochemically flexible substitutions of di-, tri-, and tetrahalopyridines: The trialkylsilyl trick

(Chemical Equation Presented) 2,4-Difluoropyridine, 2,4-dichloropyridine, 2,4,6-trifluoropyridine, 2,4,6-trichloropyridine and 2,3,4,6-tetrafluoropyridine react with standard nucleophiles exclusively at the 4-position under halogen displacement. However, the regioselectivity can be completely reversed if a trialkylsilyl group is introduced in the 5-position of the 2,4-dihalopyridines or in the 3-position of the 2,4,6-trihalopyridines or 2,3,4,6-tetrahalopyridine. Then only the halogen most remote from the bulky silyl unit (at the 2-position in the case of the 2,4-halopyridines, at the 6-position with the other substrates) gets involved in the exchange process. After removal of the silyl protective group the nucleophile is invariably found to occupy the nitrogen-neighboring position.

Rerouting nucleophilic substitution from the 4-position to the 2- or 6-position of 2,4-dihalopyridines and 2,4,6-trihalopyridines: The solution to a long-standing problem

(Chemical Equation Presented) 2,4-Difluoro-, 2,4,6-trifluoro-, and 2,3,4,6-tetrafluoropyridine undergo nucleophilic substitution preferentially if not exclusively at the 4-position. However, after the introduction of a trialkylsilyl group at C-3 or C-5, t