17228-64-7

Basic information

• Product Name: 2-Chloro-6-methoxypyridine
• Synonyms: 2-Methoxy-6-chloropyridine;6-Chloro-2-methoxypyridine;2-CHLORO-6-METHOXYPYRIDINE;2-Chloro-6-methoxypyridine, GC 98%;6-Methoxy-2-chloropyridine;2-Chloro-6-methoxypyridine,98%;2-Chlor-6-methoxypyridine;2-Chloro-6-Methoxypyridine, 98% 25GR
• CAS NO: 17228-64-7
• Molecular Formula: C₆H₆ClNO
• Molecular Weight: 143.57
• EINECS: 241-264-9
• Product Categories: Chloropyridines;Halopyridines;C6Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Heterocycle-Pyridine series;alkyl chloride
• Mol File: 17228-64-7.mol

Chemical Properties

• Boiling Point: 185-186 °C(lit.)
• Flash Point: 169 °F
• Appearance: Colorless to pale yellow liquid
• Density: 1.207 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.832mmHg at 25°C
• Refractive Index: n20/D 1.528(lit.)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 0.40±0.10(Predicted)
• BRN: 1364500
• CAS DataBase Reference: 2-Chloro-6-methoxypyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-6-methoxypyridine(17228-64-7)
• EPA Substance Registry System: 2-Chloro-6-methoxypyridine(17228-64-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39-37/39
• RIDADR: 2810
• WGK Germany: 3
• PackingGroup: III
• Hazardous Substances Data: 17228-64-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
2-Chloro-6-methoxypyridine is used as a reagent for the synthesis of imidazo[1,2-a]pyrimidines, which serve as functionally selective GABAA ligands. These ligands play a crucial role in the development of medications targeting the gamma-aminobutyric acid (GABA) receptors, which are involved in various neurological and psychiatric disorders.
Additionally, 2-Chloro-6-methoxypyridine is utilized in the synthesis of oxazolidinedione-arylpyridinones, which act as EP3 receptor antagonists. These antagonists have potential applications in the treatment of inflammatory conditions and pain management, as they modulate the prostaglandin E2 (PGE2) signaling pathway through the EP3 receptor.

InChI:InChI=1/C6H6ClNO/c1-9-6-4-2-3-5(7)8-6/h2-4H,1H3

Upstream product

• 16879-02-0 6-chloro-2-pyridone 
• 74-88-4 methyl iodide 
• 1072946-50-9 (6-chloro-2-methoxypyridin-3-yl)boronic acid 
• 40473-07-2 6-bromo-2-methoxypyridine 
• 1628-89-3 2-methoxypyridine 
• 1984-23-2 p-nitrophenyl isocyanide 
• 2402-78-0 2,6-dichloropyridine 
• 124-41-4 sodium methylate 
• 67-56-1 methanol 

Downstream Products

• 108279-32-9 2-(benzyloxy)-6-methoxypyridine 
• 35070-08-7 2-methoxy-6-phenylpyridine 
• 1251914-00-7 2-methoxy-6-(2,4,6-trifluorophenyl)pyridine 
• 1227827-90-8 C₁₂H₁₃ClN₂O₄ 
• 1227827-92-0 C₁₉H₂₀N₂O₄ 
• 1039775-38-6 2-methoxy-6-(4'-methylphenyl)pyridine 
• 1402011-06-6 C₂₂H₂₃NO₂ 
• 1402010-79-0 2-(1-(benzyloxy)-3-phenylpropyl)-6-methoxypyridine 
• 54015-96-2 6-methoxy-2-(2-pyridinyl)pyridine 
• 1394348-67-4 2-chloro-N-(1-hydroxy-cyclohexylmethyl)-5-(6-methoxy-pyridin-2-yloxy)-benzamide 
• 16879-02-0 6-chloro-2-pyridone 
• 1000512-48-0 2‐(6‐methoxypyridin‐2‐yl)acetonitrile 
• 494785-37-4 4-(6-methoxy-2-pyridinyl)phenylmethanol 

Relevant articles and documents

Reinvestigating catalytic alcohol dehydrogenation with an iridium dihydroxybipyridine catalyst

The examined catalyst [Cp*Ir(H2O)(6,6′-dhbp)]2+ (1; 6,6′-dhbp = 6,6′-dihydroxy-2,2′-bipyridine) was reported in 2012 as a highly efficient (92% conversion) and selective catalyst for the conversion of benzyl alcohol to benzaldehyde as the sole product via acceptorless dehydrogenation. We report herein that the observed conversion and selectivity data are not accurate but may have resulted, in part, from other products being produced that are not easily detected. Specifically, benzoic acid is formed as a byproduct via the disproportionation of benzaldehyde, but at high temperatures, most of the benzoic acid produced is converted in situ to benzene and carbon dioxide. While we can explain the observed selectivity, we cannot explain the observed conversion to products. In our hands, we observed 15% conversion to products under the original conditions. Other alcohol substrates were also examined and gave lower conversion to products and decreased selectivity in comparison with the original report. Acceptorless alcohol dehydrogenation to generate aldehydes is a potentially transformative technology which can allow chemists to replace stoichiometric oxidants that produce waste with efficient catalysts that only generate H2 gas as a byproduct. Thus, clarification of the 2012 report to indicate what conditions can lead to high efficiency and selectivity is a worthy topic of discussion in the literature.

Synthesis method and aftertreatment process of 6-chloro-2-hydrocarbyloxy pyridine

The invention relates to a synthesis method and an aftertreatment process of 6-chloro-2-hydrocarbyloxy pyridine. The synthesis method is characterized in that 2,6-dichloropyridine, alcohol and alkaliare used as starting raw materials; reaction is performed under the ordinary pressure and backflow state to generate 6-chloro-2-hydrocarbyloxy pyridine; the reaction conditions are mild; high conversion rate and high selectivity of the reaction are realized. The invention also relates to a treatment technology after reaction; the aftertreatment technology is simple and efficient; the circulation process is reasonably utilized for treating solid wastes and solvents; the environment protection problem in the aftertreatment process is creatively solved.

Preparation method of sodium 6-chloro-2-pyridol and 6-chloro-2-pyridone

The invention relates to a preparation method of sodium 6-chloro-2-pyridol and 6-chloro-2-pyridone. 2,6-dichloropyridin is subjected to a substitution reaction with 2-methyl-2-butanol as a solvent anda catalyst under the strongly alkaline condition under the normal pressure in a reflux state. Tests prove that 2-methyl-2-butanol is the only alcohol as the solvent and the catalyst of the reaction,so that the preparation process of 6-chloro-2-pyridol or 6-chloro-2-pyridone is greatly simplified. Compared with the prior art, the preparation method adopts a simple, efficient and environment-friendly process.

Novel synthesis method for ortho-alkane superseded pyridine

The invention relates to a novel synthesis method for ortho-alkane superseded pyridine. According to the method, ortho halogenated pyridine serves as raw materials, the ortho halogenated pyridine and corresponding alcohol react to obtain the ortho-alkane superseded pyridine under the action of sodium hydroxide. The reaction has universality for the ortho halogenated pyridine, and the method is simple and practical. Influence of consumption of the sodium hydroxide on mono-substitution and di-substitution in the reaction is inspected, alkoxy mono-substitution products and alkoxy di-substitution production are acquired, and a novel simply-operated, economical and favorable process for synthesis ortho-alkane superseded pyridine is provided.

Practical total syntheses of acromelic acids A and B

Practical total syntheses of acromelic acids A (1) and B (2), which were scarce natural products isolated from toxic mushroom by Shirahama and Matsumoto, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Beginning with regioselective transformation of symmetric 8 by either ortho-lithiation or bromination, nitroalkenes 15 and 16 were provided. Stereoselective construction of the vicinal stereocenters at the C-3, 4 positions of 1 and 2 was performed by a Ni-catalyzed asymmetric conjugate addition of α-ketoesters to the nitroalkenes. Construction of the pyrrolidine ring was accomplished in a single operation via a sequence consisting of reduction of the nitro group, intramolecular condensation with the ketone, and reduction of the resulting ketimine.

Gold-Catalyzed Proto- and Deuterodeboronation

A mild gold-catalyzed protodeboronation reaction, which does not require acid or base additives and can be carried out in "green" solvents, is described. As a result, the reaction is very functional-group-tolerant, even to acid- and base-sensitive functional groups, and should allow for the boronic acid group to be used as an effective traceless directing or blocking group. The reaction has also been extended to deuterodeboronations for regiospecific ipso-deuterations of aryls and heteroaryls from the corresponding organoboronic acid. Based on density functional theory calculations, a mechanism is proposed that involves nucleophilic attack of water at boron followed by rate-limiting B-C bond cleavage and facile protonolysis of a Au-σ-phenyl intermediate.

Practical total syntheses of acromelic acids A and B

Practical total syntheses of acromelic acids A (1) and B (2), which have potent neuro-excitatory activity, were accomplished in 13 (36% total yield) and 17 steps (6.9% total yield), respectively, from 2,6-dichloropyridine (8). Regioselective transformation of symmetric 8 provided nitroalkenes 15 and 16. The pyrrolidine ring was efficiently constructed by Ni-catalyzed asymmetric conjugate addition followed by intramolecular reductive amination.

Copper-catalyzed conversion of aryl and heteroaryl bromides into the corresponding chlorides

An efficient method for the synthesis of aryl and heteroaryl chlorides is described. The reactions of aryl and heteroaryl bromides with tetramethylammonium chloride proceeded smoothly in the presence of a copper catalyst under mild reaction conditions to produce the corresponding chlorides in satisfactory to excellent yields.

Reaction of N-fluoropyridinium fluoride with isonitriles: A convenient route to picolinamides

Reaction of N-fluoropyridinium fluoride generated in situ with a series of isonitriles led to the formation of the corresponding picolinamides in good yields. A similar reaction sequence for quinoline yielded the respective derivatives of 2-quinoline carboxylic acid. The proposed reaction mechanism involves the intermediate formation of a highly reactive carbene species.

Further studies of regioselective alkoxydehalogenation of 2,4-dichloroquinolines, 2,6-dichloropyridine and 2,4-dichloronitrobenzene

Regioselective alkoxydehalogenation reactions using solid alkoxide in toluene have been studied. 2-Alkoxy-4-haloquinolines were obtained from 2,4-dichloroquinolines. With 2,6-dichloropyridine, α-regioselectivity occurred to furnish the 2-alkoxy-6-chloropyridine. The reaction failed with 2,4-dichloronitrobenzene indicating that alkoxide surface contact with a basic heterocyclic nitrogen lone pair was essential for success. Comparative studies with the standard alkoxydehalogenation reaction (alcoholic alkoxide solution) have been performed, all compounds have been identified by 1H and 13C NMR.