1127217-94-0

Basic information

• Product Name: 5-(4-chlorophenyl)-4-methylthiazole
• Synonyms: 5-(4-chlorophenyl)-4-methylthiazole
• CAS NO: 1127217-94-0
• Molecular Weight: 209.699
• Mol File: 1127217-94-0.mol

Chemical Properties

• CAS DataBase Reference: 5-(4-chlorophenyl)-4-methylthiazole(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-chlorophenyl)-4-methylthiazole(1127217-94-0)
• EPA Substance Registry System: 5-(4-chlorophenyl)-4-methylthiazole(1127217-94-0)

Safety Data

• Hazardous Substances Data: 1127217-94-0(Hazardous Substances Data)

Upstream product

• 693-95-8 4-Methylthiazole 
• 637-87-6 1-Chloro-4-iodobenzene 
• 106-39-8 bromochlorobenzene 
• 1354455-63-2 C₅H₄NO₂S^(1-)*K⁽¹⁺⁾ 

Relevant articles and documents

Aerobic and Efficient Direct Arylation of Five-Membered Heteroarenes and Their Benzocondensed Derivatives with Aryl Bromides by Bulky α-Hydroxyimine Palladium Complexes

In the present work, a series of α-hydroxyimine palladium complexes with bulky substituents (i.e., {[Ar-N=C(R)-C(R)2-OH]PdCl2} (C1, R = Me, Ar = 2-diphenylmethyl-4,6-dimethylphenyl; C2, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methylphenyl; C3, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-methyoxylphenyl; C4, R = Me, Ar = 2,6-bis(diphenylmethyl)-4-chlorophenyl; C5, R = Ph, Ar = 2,6-dimethylphenyl; C6, R = Ph, Ar = 2,6-diisopropylphenyl)) were synthesized and characterized. The structures of palladium complexes C1 and C2 were determined by X-ray diffraction. These bidentate N,O-palladium complexes were applied for direct arylation under aerobic conditions. The effects of the reaction conditions and ligand substitution on the catalytic activity were evaluated. Upon a low palladium loading of 0.5 mol %, the bulky palladium complex C6 was successfully used to catalyze the cross-coupling of a variety of five-membered heteroarenes and their benzo-condensed derivatives with (hetero)aryl bromides. The mechanistic investigation on the direct arylation supported the involvement of a Pd(0)/Pd(II) CMD process.

Direct C-H bond (Hetero)arylation of thiazole derivatives at 5-position catalyzed by N-heterocyclic carbene palladium complexes at low catalyst loadings under aerobic conditions

A highly efficient and practical protocol has been developed for the synthesis of 5-(hetero)arylated thiazole derivatives via an N-heterocyclic carbene palladium (Pd-NHC) complex catalyzed direct C-H arylation reaction. Utilization of this methodology, th

Ferrocenyl palladacycles derived from unsymmetrical pincer-type ligands: Evidence of Pd(0) nanoparticle generation during the Suzuki-Miyaura reaction and applications in the direct arylation of thiazoles and isoxazoles

A new family of ferrocenyl-palladacycle complexes Pd(L1)Cl (Pd1) and Pd(L2)Cl (Pd2) were synthesized and characterized by UV-visible, IR, ESI-MS, and NMR spectral studies. The molecular structures of Pd1 and Pd2 were determined by X-ray crystallographic studies. Palladacycle catalyzed Suzuki-Miyaura cross-coupling reactions were investigated utilizing the derivatives of phenylboronic acids and substituted chlorobenzenes. Mechanistic investigation authenticated the generation of Pd(0) nanoparticles during the catalytic cycle and the nanoparticles were characterized by XPS, SEM and TEM analysis. Direct C-H arylation of thiazole and isoxazole derivatives employing these ferrocenyl-palladacycle complexes was examined. The reaction model for the arylation reaction implicating the in situ generation of Pd(0) nanoparticles was proposed.

Developing Bis(imino)acenaphthene-Supported N-Heterocyclic Carbene Palladium Precatalysts for Direct Arylation of Azoles

On the basis of the strategy of developing highly efficient protocol for Pd-catalyzed cross-coupling reactions, a series of bulky bis(imino)acenaphthene (BIAN)-supported Pd-PEPPSI complexes were synthesized, characterized, and applied in direct arylation

A convenient phosphine-free palladium-catalyzed direct arylation of thiazole under mild aerobic conditions

A series of bulky amine palladium complexes {[(Ar-NH2)2PdCl2]} were synthesized and characterized. The catalytic activity of the palladium complexes was evaluated via the direct C-H arylation of thiazoles with aryl bromide

A robust and efficient catalyst possessing an electron-deficient ligand for the palladium-catalyzed direct arylation of heteroarenes

The exploration of the direct arylation capacity of a unique, thermally stable, and air-stable Pd0-phosphine catalyst is reported. Besides decisively contributing to catalyst robustness, the electron-deficient trifluoromethyl-substituted triphenylphosphine ligands make the palladium center more electron-deficient and accelerate the direct arylation step. The combination of only 0.5-2 mol-% of the catalyst and a substoichiometric quantity of pivalic acid generates an efficient system to promote biaryl-forming reactions of a broad range of electronically varied hetarenes and aryl bromides. The observed regioselective arylations suggest that a concerted metalation-deprotonation pathway is involved in the C-H activation step.

Reigoselective arylation of thiazole derivatives at 5-position via Pd catalysis under ligand-free conditions

An efficient regioselective arylation of thiazole derivatives via Pd-catalyzed C-H activation is reported. The transformation was hypothesized through a Pd(0/II) catalytic cycle in the absence of special ligand sets. This method provided an efficient proc

Expanded scope of heterocyclic biaryl synthesis via a palladium-catalysed thermal decarboxylative cross-coupling reaction

The palladium-catalysed decarboxylative cross-coupling of heterocyclic aromatic carboxylates and aryl halides is described. The cross-coupling proceeds under relatively mild conditions using catalytic Pd(0) and tetrabutylammonium bromide (TBAB). Utilizing

Establishment of broadly applicable reaction conditions for the palladium-catalyzed direct arylation of heteroatom-containing aromatic compounds

Conditions for the palladium-catalyzed direct arylation of a wide range of heterocycles with aryl bromides are reported. Those conditions employ a stoichiometric ratio of both coupling partners, as well as a substoiehiometric quantity of pivalic acid, which results in significantly faster reactions. An evaluation of the influence of the nature of the aryl halide has also been carried out.