74963-04-5

Basic information

• Product Name: 5-(4-methyl phenyl)pyrimidine
• Synonyms: 5-(4-methyl phenyl)pyrimidine
• CAS NO: 74963-04-5
• Molecular Weight: 170.214
• Mol File: 74963-04-5.mol
• Article Data: 20

Chemical Properties

• CAS DataBase Reference: 5-(4-methyl phenyl)pyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(4-methyl phenyl)pyrimidine(74963-04-5)
• EPA Substance Registry System: 5-(4-methyl phenyl)pyrimidine(74963-04-5)

Safety Data

• Hazardous Substances Data: 74963-04-5(Hazardous Substances Data)

Upstream product

• 24903-95-5 nopinone 
• 7089-26-1 1,1,5,5-tetramethyl-3-(p-tolyl)-1,5-diazapentadienium perchlorate 
• 106-38-7 para-bromotoluene 
• 109299-78-7 pyrimidine 5-boronic acid 
• 624-31-7 4-tolyl iodide 
• 4595-59-9 5-bromopyrimidine 
• 31614-66-1 tributyl(p-tolyl)stannane 
• 2036-41-1 5-methylpyrimidine 
• 5720-05-8 4-methylphenylboronic acid 
• 108-88-3 toluene 
• 5720-07-0 4-methoxyphenylboronic acid 
• 289-95-2 PYRIMIDINE 
• 195062-57-8 p-tolylboronic pinacol ester 
• 69153-05-5 1-Methyl-4-((Z)-2-methylsulfanyl-vinyl)-benzene 

Downstream Products

• 74963-11-4 5-(p-tolyl)-N-phenacylpyrimidinium bromide 

Relevant articles and documents

Cyrene as a Bio-Based Solvent for the Suzuki-Miyaura Cross-Coupling

The Suzuki-Miyaura (SM) cross-coupling is the most broadly utilized Pd-catalyzed C-C bond-forming reaction in the chemical industry. A large proportion of SM couplings employ dipolar aprotic solvents; however, current sustainability initiatives and increasingly stringent regulations advocate the use of alternatives that exhibit more desirable properties. Here we describe the scope and utility of the bio-derived solvent Cyrene in SM cross-couplings and evaluate its suitability as a reaction medium for this benchmark transformation from discovery to gram scale.

Synthesis of zwitterionic palladium complexes and their application as catalysts in cross-coupling reactions of aryl, heteroaryl and benzyl bromides with organoboron reagents in neat water

N-(3-Chloro-2-quinoxalinyl)-N′-arylimidazolium salts (aryl = 2,6-diisopropylphenyl [HL1Cl]Cl, aryl = mesityl [HL2Cl]Cl) have been synthesized by treating 2,3-dichloroquinoxaline with the corresponding N′-arylimidazole in neat water. Facile reactions of these imidazolium salts with Pd(PPh3)4 and Pd2(dba)3/PPh3 (dba = dibenzyledene acetone) at 50 °C have afforded zwitterionic palladium(ii) complexes [Pd(HL1)(PPh3)Cl2] (I) and [Pd(HL2)(PPh3)Cl2] (II) in excellent yields. I and II have been tested for their ability to catalyze Suzuki-Miyaura cross coupling (SMC) reactions in neat water/K2CO3 and are found to be highly active for carrying out these reactions between aryl bromides and organoboron reagents. Furthermore, the scope of the catalyst I was also examined by employing (hetero)aryl bromides, hydrophilic aryl bromides, benzyl bromides and various organoboron reagents. More than 80 aryl/benzyl bromide-arylboronic acid combinations were screened in neat water/K2CO3 and it was found that I was a versatile catalyst, which produced biaryls/diarylmethanes in excellent yields. A TON of 82 000 was achieved by using I. Studies on the mechanism have also been carried out to investigate the involvement of carbene complexes in the catalytic path. Poison tests and a two-phase test were also conducted and the results are reported.

Oxygen-promoted Pd/C-catalyzed Suzuki-Miyaura reaction of potassium aryltrifluoroborates

A simple and highly efficient protocol has been developed for the Pd/C-catalyzed ligand-free Suzuki-Miyaura reaction of potassium aryltrifluoroborates. In this catalytic system, the results demonstrate that oxygen plays a positive role in the cross-coupling reaction. In addition, this catalytic system could be successfully applied to synthesize biaryl compounds containing a carbazole moiety and the catalyst was recycled seven times without significant loss of catalytic activity.