4-Chloro-6-trifluoromethylpyrimidine Chemical Properties

Melting point:

-53--52 °C

Boiling point:

35-36 °C(Press: 22 Torr)

Density 

1.429 g/cm3

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-4.62±0.18(Predicted)

form 

Liquid

color 

Colorless to pale yellow

InChI

InChI=1S/C5H2ClF3N2/c6-4-1-3(5(7,8)9)10-2-11-4/h1-2H

InChIKey

TYSPDLZOMUDHQZ-UHFFFAOYSA-N

SMILES

C1=NC(C(F)(F)F)=CC(Cl)=N1

CAS DataBase Reference

37552-81-1(CAS DataBase Reference)

Safety Information

Risk Statements 

36/37/38

Safety Statements 

26-36/37/39

HS Code 

2933599590

4-Chloro-6-trifluoromethylpyrimidine Usage And Synthesis

Synthesis

General procedure for the synthesis of 4-chloro-6-trifluoromethylpyrimidine from 6-trifluoromethyl-4-hydroxypyrimidine: 6-(trifluoromethyl)pyrimidin-4-ol (5.0 g, 30.5 mmol), phosphorochloridic acid chloride (3.41 mL, 36.6 mmol), and quinoline (2.16 mL, 18.3 mmol) were dissolved in toluene (50 mL), and the reaction was stirred at 100°C for 5 hours. After completion of the reaction, the reaction mixture was diluted with water and extracted three times with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product was purified by fast column chromatography (eluent: 10% ethyl acetate/hexane) to afford the target product 4-chloro-6-trifluoromethylpyrimidine (1.20 g, 21.6% yield).1H NMR (400 MHz, CDCl3) δ: 9.21 ppm (1H, s), 7.78 ppm (1H, s).

References

[1] Patent: US2006/4018, 2006, A1. Location in patent: Page/Page column 39-40
[2] Patent: US2005/209241, 2005, A1. Location in patent: Page/Page column 26
[3] Patent: WO2015/17335, 2015, A1. Location in patent: Page/Page column 66
[4] Patent: US2015/197511, 2015, A1. Location in patent: Paragraph 0393; 0394
[5] Patent: WO2015/160654, 2015, A1. Location in patent: Page/Page column 144-145

4-Chloro-6-trifluoromethylpyrimidine(37552-81-1)Related Product Information

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• Pyrimidine
• Trifluoromethanesulfonic acid
• 2-(Trifluoromethyl)benzoic acid
• 2-(Trifluoromethyl)benzyl chloride
• 2-Aminobenzotrifluoride
• Epichlorohydrin
• 3-(Trifluoromethyl)benzaldehyde
• Pirimiphos-methyl
• Chloroacetic acid
• Difluorochloromethane
• 4-CHLORO-2-(METHYLSULFANYL)-6-(TRIFLUOROMETHYL)PYRIMIDINE
• 2-AMINO-4-CHLORO-6-TRIFLUOROMETHYL-PYRIMIDINE
• Methyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate
• 2,4-dichloro-6-(trifluoromethyl)pyrimidine
• ETHYL 2-CHLORO-4-(TRIFLUOROMETHYL)PYRIMIDINE-5-CARBOXYLATE
• 4-CHLORO-2-(TRIFLUOROMETHYL)PYRIMIDINE
• 2-Chloro-4-(trifluoromethyl)pyrimidine