149879-32-3

Basic information

• Product Name: Pyridine, 2-chloro-5-(phenylmethyl)-
• CAS NO: 149879-32-3
• Molecular Formula: C12H10ClN
• Mol File: 149879-32-3.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Pyridine, 2-chloro-5-(phenylmethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine, 2-chloro-5-(phenylmethyl)-(149879-32-3)
• EPA Substance Registry System: Pyridine, 2-chloro-5-(phenylmethyl)-(149879-32-3)

Safety Data

• Hazardous Substances Data: 149879-32-3(Hazardous Substances Data)

Upstream product

• 70258-18-3 2-chloro-5-(chloromethyl)pyridine 
• 2996-92-1 phenyl trimethylsiloxane 
• 98-80-6 phenylboronic acid 

Relevant articles and documents

A Zwitterionic Palladium(II) Complex as a Precatalyst for Neat-Water-Mediated Cross-Coupling Reactions of Heteroaryl, Benzyl, and Aryl Acid Chlorides with Organoboron Reagents

The Suzuki–Miyaura cross-coupling (SMC) reactions of several heteroaryl chlorides, benzyl chlorides, and aryl acid chlorides with (hetero)arylboron reagents have been investigated in the presence of [Pd(HL1)(PPh3)Cl2] (I) [HL1 = 3-[(2,6-diisopropylphenyl)-1-imidazolio]-2-quinoxalinide] as catalyst and K2CO3 as base in neat water. The synthesis of the heterocycle-containing biaryls required the addition of 2 mol-% of a phosphine ligand (PPh3 or X-Phos). A combination of more than 115 substrates were screened and it was found that I is a versatile catalyst that can produce heterocycle-containing biaryls, diarylmethanes, and benzophenones in moderate-to-excellent yields.

First cross-coupling reaction of potassium aryltrifluoroborates with organic chlorides in aqueous media catalyzed by an oxime-derived palladacycle

(Chemical Equation Presented) Potassium aryltrifluoroborates are cross-coupled with aryl and heteroaryl chlorides using a 4-hydroxyacetophenone oxime-derived palladacycle as precatalyst, K2CO3 as base, and TBAB as additive in refluxing water under conventional and microwave heating affording the corresponding biphenyls under phosphine-free conditions. For the arylation of allyl and benzyl chlorides, KOH is used as base in acetone-water (3:2) at rt or 50 °C using 0.1 mol % Pd loading providing allylbenzenes and diarylmethanes, respectively.

Cross-coupling reactions with boronic acids in water catalysed by oxime-derived palladacycles

Palladacycles derived from phenone-oximes 1 are efficient precatalysts for the Suzuki-Miyaura coupling of arylboronic acids with aromatic and heteroaromatic bromides and chlorides under water reflux under aerobic conditions. Alternatively, the coupling can also be carried out at room temperature in methanol-water. Aryl bromides gave biaryls with TON up to 105 and TOF up to 7 × 104 h-1. Activated and deactivated aryl chlorides need the presence of TBAB for the couplings, showing slightly lower efficiency (TON up to 9000 and TOF up to 3850 h-1). C(sp2)-C(sp3) bonds can also be formed by cross-coupling reactions of trimethylboroxine and butylboronic acid with aromatic bromides and chlorides under water reflux and of benzylic and allylic chlorides or acetates with arylboronic acids in acetone-water at room temperature.