Production Method 1

18368-63-3

1719-19-3

96206-92-7

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Tetrabutylammonium bromide Catalysts: Palladium chloride ,  X-Phos Solvents: Water ;  24 h, 120 °C

Reference

Palladium-catalyzed deacetonative coupling of aryl propargylic alcohols with aryl chlorides in water

Chang, Feng; Liu, Yanping, Synthetic Communications, 2017, 47(10), 961-967

Production Method 2

5315-25-3

96206-92-7

Reaction Conditions

1.1 Catalysts: Triphenylphosphine ,  Di-μ-chlorobis(η3-2-propenyl)dipalladium Solvents: 1-Butyl-3-methylimidazolium tetrafluoroborate ;  10 min, rt; 60 °C; cooled
1.2 Reagents: Pyrrolidine ;  4 h, 100 °C

Reference

Double arylation of diynes and alkynylation of functionalized heteroaryl halides by a practical heck reaction in an ionic liquid

Saleh, Samer; Picquet, Michel; Meunier, Philippe; Hierso, Jean-Cyrille, Synlett, 2011, (19), 2844-2848

Production Method 3

591-50-4

656800-40-7

96206-92-7

Reaction Conditions

1.1 Reagents: Tetrabutylammonium fluoride Catalysts: Triphenylphosphine ,  Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium Solvents: Tetrahydrofuran ,  Triethylamine ;  50 °C

Reference

Synthesis and biological evaluation of fenobam analogs as mGlu5 receptor antagonists

Jaeschke, Georg; Porter, Richard; Buettelmann, Bernd; Ceccarelli, Simona M.; Guba, Wolfgang; et al, Bioorganic & Medicinal Chemistry Letters, 2007, 17(5), 1307-1311

Production Method 4

5315-25-3

96206-92-7

Reaction Conditions

Reference

Thermal rearrangements of cyclic amine ylides. VIII. Intramolecular cyclization of 2-ethynylpyridine N-ylides into indolizines and cycl[3.2.2]azines

Sashida, Haruki; Kato, Masanobu; Tsuchiya, Takashi, Chemical & Pharmaceutical Bulletin, 1988, 36(10), 3826-32

Production Method 5

2102345-08-2

96206-92-7

Reaction Conditions

1.1 Catalysts: Dibutyltin oxide ,  Azidotrimethylsilane Solvents: Toluene ;  4 h, reflux

Reference

Transformation of Carbonyl Compounds into Homologous Alkynes under Neutral Conditions: Fragmentation of Tetrazoles Derived from Cyanophosphates

Yoneyama, Hiroki; Numata, Masahiro; Uemura, Kenji; Usami, Yoshihide; Harusawa, Shinya, Journal of Organic Chemistry, 2017, 82(11), 5538-5556

Production Method 6

5315-25-3

637-44-5

96206-92-7

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: (SP-4-3)-[3-[[(1,1-Dimethylethyl)(oxido-κO)imino]methyl]-N-[(2-pyridinyl-κN)meth… Solvents: Dimethylformamide ;  1 h, 140 °C

Reference

Phosphine-Free Palladium-Catalyzed Decarboxylative Coupling of Alkynylcarboxylic Acids with Aryl and Heteroaryl Halides

Reddy, Police Vishnuvardhan; Srinivas, Pottabathula; Annapurna, Manne; Bhargava, Suresh; Wagler, Jorg; et al, Advanced Synthesis & Catalysis, 2013, 355(4), 705-710

Production Method 7

96206-92-7

Reaction Conditions

Reference

Preparation of phenylacetylene and pyridineacetylene derivatives, in particular MPEP and intermediates of erlotinib, rofecoxib and tazarotene

, Italy, , ,

Production Method 8

96206-92-7

Reaction Conditions

Reference

Exploration of Allosteric Agonism Structure-Activity Relationships within an Acetylene Series of Metabotropic Glutamate Receptor 5 (mGlu5) Positive Allosteric Modulators (PAMs): Discovery of 5((3-Fluorophenyl)ethynyl)N(3-methyloxetan-3-yl)picolinamide (ML254)

Turlington, Mark; Noetzel, Meredith J.; Chun, Aspen; Zhou, Ya; Gogliotti, Rocco D.; et al, Journal of Medicinal Chemistry, 2013, 56(20), 7976-7996

Production Method 9

5315-24-2

96206-92-7

Reaction Conditions

1.1 Reagents: Potassium carbonate ,  Oxygen Catalysts: Cuprous chloride Solvents: Methanol ;  10 h, 1 atm, 25 - 28 °C

Reference

Visible-light induced copper(I)-catalyzed denitrogenative oxidative coupling of hydrazinylpyridines with terminal alkynes

Charpe, Vaibhav Pramod; Hande, Aniket A.; Sagadevan, Arunachalam; Hwang, Kuo Chu, Green Chemistry, 2018, 20(21), 4859-4864

Production Method 10

5315-25-3

96206-92-7

Reaction Conditions

1.1 Reagents: Diethylamine Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium ;  rt → 55 °C; 15 h, 55 °C

Reference

Simultaneous rapid reaction workup and catalyst recovery

Lu, Zhichao; Hetman, Zofia; Hammond, Gerald B.; Xu, Bo, Green Chemistry, 2016, 18(21), 5769-5772

Production Method 11

5315-25-3

96206-92-7

Reaction Conditions

1.1 Reagents: Triethylamine ,  Cesium carbonate Catalysts: Triphenylphosphine Solvents: Dimethylacetamide ;  12 h, 130 °C

Reference

Transition-Metal-Free Coupling Reactions: PPh3-Promoted Sonogashira-Type Cross-Couplings of Heteroaryl Halides with Terminal Alkynes

Tian, Wan-Fa; He, Ke-Han; Li, Na; Fen; Liu; et al, ChemistrySelect, 2020, 5(15), 4496-4499

Production Method 12

7714-33-2

96206-92-7

Reaction Conditions

1.1 Catalysts: Palladium diacetate ,  Bis[2-(diphenylphosphino)phenyl] ether Solvents: Tetrahydrofuran ;  10 min, rt
1.2 rt; 4 h, 50 °C
1.3 Reagents: Ammonium chloride Solvents: Water ;  50 °C

Reference

A novel palladium-catalyzed cross-coupling of thiomethylated alkynes with functionalized organozinc reagents

Melzig, Laurin; Stemper, Jeremy; Knochel, Paul, Synthesis, 2010, (12), 2085-2091

Production Method 13

5315-25-3

96206-92-7

Reaction Conditions

1.1 Reagents: Diisopropylamine Catalysts: Cuprous iodide ,  Dichlorobis(triphenylphosphine)palladium ;  4 h, rt → 80 °C

Reference

Mononuclear and dinuclear heteroleptic Cu(I) complexes based on pyridyl-triazole and DPEPhos with long-lived excited-state lifetimes

Bizzarri, Claudia ; Arndt, Andreas P. ; Kohaut, Stephan; Fink, Karin ; Nieger, Martin, Journal of Organometallic Chemistry, 2018, 871, 140-149

Production Method 14

5315-25-3

2170-06-1

96206-92-7

Reaction Conditions

1.1 Reagents: Sodium acetate ,  Tetrabutylammonium chloride Catalysts: Palladium diacetate ,  Tri-o-tolylphosphine Solvents: Dimethylformamide ;  2.5 min, 120 °C

Reference

Copper-free palladium-catalyzed Sonogashira-type coupling of aryl halides and 1-aryl-2-(trimethylsilyl)acetylenes

Sorensen, Ulrik S.; Pombo-Villar, Esteban, Tetrahedron, 2005, 61(10), 2697-2703

Production Method 15

5315-25-3

2170-06-1

96206-92-7

Reaction Conditions

1.1 Reagents: Tetrabutylammonium chloride Catalysts: Palladium diacetate Solvents: Dimethylformamide ;  15 min, 100 °C

Reference

Palladium-catalyzed coupling of silyl-acetylenes to aryl halides using microwave irradiation

Sorensen, Ulrik S.; Wede, Judith; Pombo-Villar, Esteban, International Electronic Conferences on Synthetic Organic Chemistry, 2004, 1953, 1953-1956

Production Method 16

5315-25-3

96206-92-7

Reaction Conditions

Reference

Thermal intramolecular cyclization of 2-ethynylpyridine N-ylides to indolizines and cyclazines

Tsuchiya, Takashi; Kato, Masanobu; Sashida, Haruki, Chemical & Pharmaceutical Bulletin, 1984, 32(11), 4666-9

Production Method 17

931-19-1

33440-88-9

96206-92-7

66310-15-4

Reaction Conditions

1.1 Reagents: Benzoyl chloride Solvents: Benzene
1.2 -

Reference

Novel ethynylation of pyridines by a Reissert-Henze-type reaction

Nishiwaki, Nagatoshi; Minakata, Satoshi; Komatsu, Mitsuo; Ohshiro, Yoshiki, Chemistry Letters, 1989, (5), 773-6

2-methyl-6-(2-phenylethynyl)pyridine Raw materials

• Iodobenzene
• 2-Hydrazinyl-6-methylpyridine
• 2-Bromo-6-methylpyridine
• 2-Chloro-6-methylpyridine
• Benzene, [(methylthio)ethynyl]-
• 2-Methyl-4-phenylbut-3-yn-2-ol
• Phosphoric acid, cyano(6-methyl-2-pyridinyl)phenylmethyl diethyl ester
• 2-Picoline N-oxide
• Phenylpropiolic acid
• 1-Phenyl-2-(trimethylsilyl)acetylene
• Pyridine, 2-methyl-6-[(trimethylsilyl)ethynyl]-
• silver phenylacetylenide

2-methyl-6-(2-phenylethynyl)pyridine Preparation Products

• 2-Pyridinemethanol, benzoate (ester) (66310-15-4)
• 2-methyl-6-(2-phenylethynyl)pyridine (96206-92-7)

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• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyridines and derivatives Methylpyridines
• Other Chemical additives Functional Additives

Professional Introduction to 2-methyl-6-(2-phenylethynyl)pyridine (CAS No. 96206-92-7)

2-methyl-6-(2-phenylethynyl)pyridine, a compound with the chemical identifier CAS No. 96206-92-7, is a significant molecule in the field of pharmaceutical chemistry and organic synthesis. This compound belongs to the pyridine class of heterocyclic aromatic compounds, characterized by a nitrogen atom incorporated into a six-membered ring structure. The presence of both a methyl group and a phenylethynyl substituent at specific positions on the pyridine ring imparts unique electronic and steric properties, making it a valuable scaffold for the development of various chemical entities.

The molecular structure of 2-methyl-6-(2-phenylethynyl)pyridine consists of a pyridine core substituted at the 2-position with a methyl group and at the 6-position with a phenylethynyl group. The phenylethynyl moiety, which is an aromatic ring attached to an alkyne group, introduces significant reactivity and functionality to the molecule. This combination of structural features has garnered interest in medicinal chemistry due to its potential as a building block for more complex pharmacophores.

In recent years, there has been growing interest in the development of novel heterocyclic compounds for their applications in drug discovery and material science. Pyridine derivatives, in particular, have been extensively studied due to their broad spectrum of biological activities. The compound 2-methyl-6-(2-phenylethynyl)pyridine has been explored in various contexts, including its role as an intermediate in synthesizing more complex molecules with potential therapeutic applications.

One of the most compelling aspects of 2-methyl-6-(2-phenylethynyl)pyridine is its versatility in organic synthesis. The presence of both electron-donating and electron-withdrawing groups allows for diverse chemical transformations, including cross-coupling reactions, nucleophilic substitutions, and metal-catalyzed reactions. These properties make it an attractive candidate for use in synthetic methodologies that aim to construct complex molecular architectures.

The phenylethynyl group in particular has been recognized for its ability to participate in various types of chemical reactions, such as Sonogashira couplings, which are widely used in pharmaceutical synthesis. This reactivity has enabled researchers to incorporate this compound into larger molecules with specific biological activities. For instance, derivatives of 2-methyl-6-(2-phenylethynyl)pyridine have been investigated for their potential as kinase inhibitors, given the importance of kinase enzymes in various disease pathways.

Recent studies have also highlighted the compound's role in materials science. The electronic properties of pyridine derivatives can be tuned by modifying substituents on the ring, leading to materials with unique conductive or luminescent characteristics. The alkyne functionality in 2-methyl-6-(2-phenylethynyl)pyridine further enhances its utility in this area by providing additional sites for functionalization and interaction with other materials.

The synthesis of 2-methyl-6-(2-phenylethynyl)pyridine typically involves multi-step organic reactions that require careful optimization to achieve high yields and purity. Common synthetic routes include the palladium-catalyzed coupling of halogenated pyridines with terminal alkynes, followed by functional group transformations to introduce the desired substituents. Advances in catalytic methods have significantly improved the efficiency and scalability of these synthetic processes.

In terms of biological activity, preliminary studies on derivatives of 2-methyl-6-(2-phenylethynyl)pyridine have shown promising results in several areas. For example, certain analogs have demonstrated inhibitory effects on enzymes involved in inflammatory pathways, suggesting potential applications in treating inflammatory diseases. Additionally, the compound's ability to interact with biological targets has led to investigations into its role as an antimicrobial agent.

The structural features of 2-methyl-6-(2-phenylethynyl)pyridine also make it a suitable candidate for further derivatization to explore new chemical space. By introducing additional functional groups or modifying existing ones, researchers can generate libraries of compounds with tailored properties for specific applications. This approach aligns with modern drug discovery strategies that emphasize diversity-oriented synthesis (DOS) to accelerate the identification of novel bioactive molecules.

The compound's electronic properties have also been explored in the context of organic electronics. Pyridine derivatives are known for their ability to act as ligands or anchors in coordination complexes with transition metals, which can be used in catalysis or as components in electronic devices. The presence of both aromatic and alkyne functionalities provides additional opportunities for tuning these properties through strategic functionalization.

In conclusion, 2-methyl-6-(2-phenylethynyl)pyridine (CAS No. 96206-92-7) is a versatile and multifaceted compound with significant potential in pharmaceutical chemistry and materials science. Its unique structural features enable diverse chemical transformations and biological activities, making it a valuable scaffold for further exploration. As research continues to uncover new applications for this compound and its derivatives, it is likely to remain an important molecule in both academic and industrial settings.

• 70437-12-6(Isoquinoline, 3-(phenylethynyl)-)
• 13141-42-9(2-(2-phenylethynyl)pyridine)
• 219911-35-0(MPEP Hydrochloride)
• 83965-72-4(Pyridine, 2,6-bis(phenylethynyl)-)
• 823198-93-2(Pyridine, 2-methyl-6-(4-pyridinylethynyl)-, dihydrochloride)
• 823198-73-8(Pyridine, 4-methyl-2-(phenylethynyl)-, hydrochloride)
• 823198-75-0(Pyridine, 2,4-dimethyl-6-(phenylethynyl)-, hydrochloride)
• 824389-28-8(Pyridine,2,4-dimethyl-6-(2-phenylethynyl)-)
• 80221-14-3(Pyridine, 2-[(4-methylphenyl)ethynyl]-)
• 70437-09-1(Isoquinoline, 1-(phenylethynyl)-)