69034-12-4 | Pyrimidine, 2-chloro-5-(trifluoromethyl)- (9CI)

CAS:69034-12-4 | Pyrimidine, 2-chloro-5-(trifluoromethyl)- (9CI),Description

2-Chloro-5-(trifluoromethyl)pyrimidine is a pyrimidine derivative. It has the empirical formula C5H2ClF3N2 and a molecular weight of 182.53. The systematic name for this compound is 2-Chloro-5-(trifluoromethyl)pyrimidine.

Synthesis Analysis

The synthesis of 2-Chloro-5-(trifluoromethyl)pyrimidine involves the reaction of 2-chloro-5-trifluoromethylpyridine with ferric chloride. The reaction is carried out at a temperature of 150-170 °C for 18 hours.

Molecular Structure Analysis

The molecular structure of 2-Chloro-5-(trifluoromethyl)pyrimidine is represented by the SMILES string FC(F)(F)c1cnc(Cl)nc1. The InChI string for this compound is InChI=1S/C5H2ClF3N2/c6-4-10-1-3(2-11-4)5(7,8)9/h1-2H.

Chemical Reactions Analysis

The chloride in 2-Chloro-5-(trifluoromethyl)pyrimidine can be transformed into a 4H-pyran-4-one intermediate by the synthesis of (E)-4-methoxybut-3-en-2-one with LiHMDS at -78 °C, followed by TFA-mediated cyclization.

Physical And Chemical Properties Analysis

2-Chloro-5-(trifluoromethyl)pyrimidine is a solid with a melting point of 48-52 °C. It has a density of 1.5±0.1 g/cm3 and a boiling point of 222.1±35.0 °C at 760 mmHg. The compound has a vapor pressure of 0.2±0.4 mmHg at 25°C.

Scientific Research Applications

Synthesis and Functionalization

2-Chloro-5-(trifluoromethyl)pyrimidine is utilized in the synthesis of various chemical compounds. For instance, it is involved in generating metal-bearing and trifluoromethyl-substituted pyrimidines. This compound can yield 5-carboxylic acids when treated with isopropylmagnesium chloride or butyllithium followed by carboxylation. Such reactions are significant in producing specialized chemical structures for further research and application in various fields (Schlosser, Lefebvre, & Ondi, 2006) .

Role in Medicinal Chemistry

2-Chloro-5-(trifluoromethyl)pyrimidine has applications in medicinal chemistry. It serves as a core structure in synthesizing inhibitors that target NF-kappaB and AP-1 gene expression. Such compounds are significant in exploring potential treatments for various diseases. The compound's structure allows for modifications, which can lead to the development of new therapeutic agents (Palanki et al., 2000).

Applications in Organic Electronics

The compound is also used in creating new classes of organic electronics. It has been employed in synthesizing heteroleptic Ir(III) metal complexes, which show promise in the development of organic light-emitting diodes (OLEDs). Such applications are crucial for advancing technology in display and lighting systems (Chang et al., 2013).

Antiviral and Anticancer Research

This compound plays a role in the development of antiviral and anticancer drugs. For example, derivatives of 2-Chloro-5-(trifluoromethyl)pyrimidine have been synthesized and evaluated for their antiproliferative activity on cancer cell lines, demonstrating potential therapeutic applications in oncology (Becan et al., 2022).

Diverse Synthetic Intermediates

2-Chloro-5-(trifluoromethyl)pyrimidine acts as a versatile synthetic intermediate in various chemical reactions. It is used for synthesizing diverse chemical structures, indicating its broad application in synthetic chemistry. This versatility is essential for creating compounds with potential applications in different scientific fields (Tang, Wang, Li, & Wang, 2014).

Safety And Hazards

2-Chloro-5-(trifluoromethyl)pyrimidine is classified as Acute Tox. 3 Oral, Eye Irrit. 2, Skin Irrit. 2, and STOT SE 3. It is recommended to avoid dust formation, breathing mist, gas or vapors, and contact with skin and eyes. Use of personal protective equipment and chemical impermeable gloves is advised.

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