4385-63-1

Basic information

• Product Name: 2-(4-METHOXYPHENYL)-6-METHYLPYRIDINE
• Synonyms: 2-(4-METHOXYPHENYL)-6-METHYLPYRIDINE
• CAS NO: 4385-63-1
• Molecular Formula: C₁₃H₁₃NO
• Molecular Weight: 0
• Mol File: 4385-63-1.mol
• Article Data: 16

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-(4-METHOXYPHENYL)-6-METHYLPYRIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXYPHENYL)-6-METHYLPYRIDINE(4385-63-1)
• EPA Substance Registry System: 2-(4-METHOXYPHENYL)-6-METHYLPYRIDINE(4385-63-1)

Safety Data

• Hazardous Substances Data: 4385-63-1(Hazardous Substances Data)

Usage

Structure

Pyridine derivative with a 2-(4-methoxyphenyl) and 6-methyl substituent

Usage

Building block in the synthesis of pharmaceuticals and agrochemicals, research chemical in the development of new drugs and materials

Physical state

Solid at room temperature

Handling and storage

Dry, cool environment

Safety precautions

Potential health and safety hazards if mishandled

Upstream product

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• 161891-26-5 3-chloro-3-(4-methoxyphenyl)acrylaldehyde 
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• 621685-64-1 (6-methylpyridin-2-yl)magnesium bromide 
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• 14401-91-3 picoline hydrochloride 
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Relevant articles and documents

Desulfonative Suzuki–Miyaura Coupling of Sulfonyl Fluorides

Sulfonyl fluorides have emerged as powerful “click” electrophiles to access sulfonylated derivatives. Yet, they are relatively inert towards C?C bond forming transformations, notably under transition-metal catalysis. Here, we describe conditions under which aryl sulfonyl fluorides act as electrophiles for the Pd-catalyzed Suzuki–Miyaura cross-coupling. This desulfonative cross-coupling occurs selectively in the absence of base and, unusually, even in the presence of strong acids. Divergent one-step syntheses of two analogues of bioactive compounds showcase the expanded reactivity of sulfonyl fluorides to encompass both S?Nu and C?C bond formation. Mechanistic experiments and DFT calculations suggest oxidative addition occurs at the C?S bond followed by desulfonation to form a Pd-F intermediate that facilitates transmetalation.

Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions

Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.

Formate-Mediated Cross-Electrophile Reductive Coupling of Aryl Iodides and Bromopyridines

Two catalytic systems for the formate-mediated cross-electrophile reductive coupling of aryl iodides with 6-bromopyridines are described. Using homogenous rhodium or heterogeneous palladium catalysts, the products of reductive biaryl cross-coupling could