136547-16-5

Basic information

• Product Name: Pyrimidine, 4-(trifluoromethyl)- (9CI)
• Synonyms: Pyrimidine, 4-(trifluoromethyl)- (9CI);4-Trifluoromethylpyrimidine
• CAS NO: 136547-16-5
• Molecular Formula: C5H3F3N2
• Molecular Weight: 148.0859296
• Product Categories: PYRIMIDINE
• Mol File: 136547-16-5.mol

Chemical Properties

• Boiling Point: 137.9 °C at 760 mmHg
• Flash Point: 37.2 °C
• Appearance: /
• Density: 1.353 g/cm³
• Vapor Pressure: 8.58mmHg at 25°C
• Refractive Index: 1.415
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Pyrimidine, 4-(trifluoromethyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine, 4-(trifluoromethyl)- (9CI)(136547-16-5)
• EPA Substance Registry System: Pyrimidine, 4-(trifluoromethyl)- (9CI)(136547-16-5)

Safety Data

• Hazardous Substances Data: 136547-16-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
Pyrimidine, 4-(trifluoromethyl)(9CI) is utilized as a building block in the synthesis of biologically active molecules, contributing to the development of new pharmaceutical agents. Its unique structure and properties make it a valuable component in creating innovative drug candidates.
Used in Agrochemical Research:
In the agrochemical industry, Pyrimidine, 4-(trifluoromethyl)(9CI) serves as a key component in the synthesis of various agrochemicals, including pesticides and herbicides. Its incorporation into these products enhances their effectiveness in controlling pests and weeds, thereby improving crop yields and quality.
Used in Organic Synthesis:
Pyrimidine, 4-(trifluoromethyl)(9CI) acts as a reagent in organic synthesis, facilitating the formation of a wide range of chemical compounds. Its versatility and reactivity make it a valuable tool in the synthesis of complex organic molecules for various applications.
Used in Specialty Chemicals Production:
As a precursor in the production of specialty chemicals, Pyrimidine, 4-(trifluoromethyl)(9CI) contributes to the manufacturing of a variety of industrial products. Its unique properties enable the creation of specialized chemicals with specific applications in various industries.
Used in Drug Discovery and Development:
Pyrimidine, 4-(trifluoromethyl)(9CI) holds potential in drug discovery and development, as its incorporation into drug candidates can lead to the creation of novel therapeutic agents with improved efficacy and selectivity. Its unique structure and properties make it a promising candidate for the development of new drugs targeting various diseases and conditions.

InChI:InChI=1/C5H3F3N2/c6-5(7,8)4-1-2-9-3-10-4/h1-3H

Upstream product

• 59938-06-6 (E)-4-Ethoxy-1,1,1-trifluoro-3-buten-2-one 
• 3473-63-0 formamidine acetic acid 
• 136547-17-6 4-trifluoromethyl-2-mercaptopyrimidine 
• 59938-06-6 4-ethoxy-1,1,1-trifluoro-3-butene-2-one 
• 77287-34-4 formamide 

Relevant articles and documents

The synthesis of nebularine and its analogs via oxidative desulfuration in aqueous nitric acid

The synthesis of nebularine and its analogs has been achieved via oxidative desulfuration in H2O for the first time. With 50% HNO3as an oxidant and solvent, 18 products were obtained in good yields (70%–94%). The oxidative desulfuration system could tolerate different functional groups including fluoro, chloro, amino, alkyl, allyl, ribosyl, deoxyribosyl, and arabinofuranosyl groups.More importantly, the drug nebularine could be obtained successfully on a 20 g scale, which made this route more attractive for industrial applications.

Electron-deficient heteroarenium salts: An organocatalytic tool for activation of hydrogen peroxide in oxidations

A series of monosubstituted pyrimidinium and pyrazinium triflates and 3,5-disubstituted pyridinium triflates were prepared and tested as simple catalysts of oxidations with hydrogen peroxide, using sulfoxidation as a model reaction. Their catalytic efficiency strongly depends on the type of substituent and is remarkable for derivatives with an electron-withdrawing group, showing reactivity comparable to that of flavinium salts which are the prominent organocatalysts for oxygenations. Because of their high stability and good accessibility, 4-(trifluoromethyl)pyrimidinium and 3,5-dinitropyridinium triflates are the catalysts of choice and were shown to catalyze oxidation of aliphatic and aromatic sulfides to sulfoxides, giving quantitative conversions, high preparative yields and excellent chemoselectivity. The high efficiency of electron-poor heteroarenium salts is rationalized by their ability to readily form adducts with nucleophiles, as documented by low pKR+ values (pKR+ red > -0.5 V). Hydrogen peroxide adducts formed in situ during catalytic oxidation act as substrate oxidizing agents. The Gibbs free energies of oxygen transfer from these heterocyclic hydroperoxides to thioanisole, obtained by calculations at the B3LYP/6-311++g(d,p) level, showed that they are much stronger oxidizing agents than alkyl hydroperoxides and in some cases are almost comparable to derivatives of flavin hydroperoxide acting as oxidizing agents in monooxygenases.

Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water

A simple dehydrazination reaction has been achieved in the presence of a catalytic amount of CuSO4 for the first time. With CuSO4 (2 mol%) as a catalyst and water as a solvent, the dehydrazination products were obtained in good yields (66-95%). Moreover, the drugs nebularine and vidarabine were afforded successfully, and vidarabine could be produced on a 0.923 kg scale, which shows good potential for industrial applications.

4-TRIFLUOROMETHYLPYRIMIDINES

It is shown that β-alkoxyvinyl trifluoromethyl ketones are convenient reagents for the synthesis of 4-trifluoromethylpyrimidines that contain a hydrogen atom or hydroxy, mercapto, and amino groups in the 2 position.The NMR, IR, and UV spectra of the synth