672-45-7

Basic information

• Product Name: 6-(TRIFLUOROMETHYL)URACIL
• Synonyms: 6-(TRIFLUOROMETHYL)URACIL;6-(TRIFLUOROMETHYL)URACYL;6-(TRIFLUOROMETHYL)-2,4-(1H,3H)PYRIMIDINEDIONE;2,4(1H,3H)-Pyrimidinedione, 6-(trifluoromethyl)-;6-(Trifluoromethyl)-2,4-pyrimidinediol;6-Trifluoromethyl-1H-pyrimidine-2,4-dione;6-(Trifluoromethyl)pyrimidine-2,4(1H,3H)-dione;2,4-Dihydroxy-6-trifluoromethylpyrimidine
• CAS NO: 672-45-7
• Molecular Formula: C₅H₃F₃N₂O₂
• Molecular Weight: 180.08
• EINECS: 211-593-2
• Product Categories: Pyrimidine series;Heterocyclic Compounds;Building Blocks;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 672-45-7.mol
• Article Data: 8

Chemical Properties

• Melting Point: 230-235 °C(lit.)
• Boiling Point: 391.3 °C at 760 mmHg
• Flash Point: 190.5 °C
• Appearance: /Powder
• Density: 1.554 g/cm³
• Vapor Pressure: 1.1E-06mmHg at 25°C
• Refractive Index: 1.427
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: 4.70±0.10(Predicted)
• CAS DataBase Reference: 6-(TRIFLUOROMETHYL)URACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 6-(TRIFLUOROMETHYL)URACIL(672-45-7)
• EPA Substance Registry System: 6-(TRIFLUOROMETHYL)URACIL(672-45-7)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 672-45-7(Hazardous Substances Data)

Usage

Uses

6-(Trifluoromethyl)-2,4(1H,3H)-pyrimidinedione is an anticancer drug, produced from catalytic trifluoromethylation of uracil.

Synthesis Reference(s)

The Journal of Organic Chemistry, 24, p. 113, 1959 DOI: 10.1021/jo01083a607

InChI:InChI=1/C5H3F3N2O2/c6-5(7,8)2-1-3(11)10-4(12)9-2/h1H,(H2,9,10,11,12)

Upstream product

• 836-12-4 (6-oxo-4-trifluoromethyl-1,6-dihydropyrimidin-2-ylsulfanyl)acetic acid 
• 175354-56-0 2-Methoxy-6-trifluoromethyl-3H-pyrimidin-4-one 
• 368-54-7 2-sulfanylidene-6-(trifluoromethyl)-2,3-dihydropyrimidin-4(1H)-one 
• 368-54-7 6-trifluoromethyl-4-hydroxy-2-mercaptopyrimidine 
• 178813-85-9 C₇H₇F₃N₂O₂ 
• 16097-63-5 4-Chloro-2-methylthio-6-(trifluoromethyl)pyrimidine 
• 16097-62-4 4-hydroxy-2-(methylthio)-6-(trifluoromethyl)pyrimidine 
• 624-83-9 methyl isocyanate 
• 372-29-2 ethyl 3-amino-4,4,4-trifluoro-2-butenoate 
• 16097-62-4 2-(methylsulfanyl)-6-(trifluoromethyl)pyrimidin-4(3H)-one 
• 657-58-9 2-ethylmercapto-6-trifluoromethyl-3H-pyrimidin-4-one 
• 93669-61-5 4-N-Methylanilino-2-methylthio-6-trifluoromethylpyrimidine 
• 372-31-6 ethyl 4,4,4-trifluoroacetoacetate 
• 57-13-6 urea 

Downstream Products

• 114963-93-8 4-Chloro-2-N,N-di-n-propylamino-6-trifluoromethylpyrimidine 
• 114963-82-5 2-Chloro-4-N,N-di-n-propylamino-6-trifluoromethylpyrimidine 
• 16097-64-6 2,4-dichloro-6-(trifluoromethyl)-pyrimidine 
• 114963-83-6 2-Chloro-4-N,N-di-n-butylamino-6-trifluoromethylpyrimidine 
• 114963-94-9 4-Chloro-2-N,N-di-n-butylamino-6-trifluoromethylpyrimidine 
• 85730-40-1 5-Chloro-6-trifluoromethyluracil 
• 85730-34-3 4-Chloro-6-trifluoromethylpyrimidin-2-yldichlorophosphate 
• 93669-52-4 4-Chloro-2-N-methylanilino-6-trifluoromethylpyrimidine 
• 93669-54-6 2,4-bis(N-Methylanilino)-6-trifluoromethylpyrimidine 
• 114963-81-4 2-Chloro-4-N,N-diethylamino-6-trifluoromethylpyrimidine 
• 114963-92-7 4-Chloro-2-N,N-diethylamino-6-trifluoromethylpyrimidine 

Relevant articles and documents

HEPATITIS B VIRAL ASSEMBLY EFFECTORS

Novel assembly effector compounds having a therapeutic effect against hepatitis B viral (HBV) infection are disclosed. Assembly effector molecules described herein can lead to defective viral assembly and also may affect other viral activities associated with chronic HBV infection. Also disclosed is a process to synthesize disclosed compounds, method of treatment of HBV by administration of disclosed compounds, and use of these compounds in the manufacture of medicaments against HBV.

ANTIVIRAL PYRIMIDINES

Disclosed herein are novel compounds comprising substituted pyrimidines, pyrazolopyrimtdines, and imidazolopyrimidines, the syntheses thereof, and compositions thereof, including pharmaceutical compositions, comprising the novel pyrimidines, pyrazolopyrimtdines, imidazolpyrimidines and related compounds. Such compounds function to inhibit entry of viruses of the Flaviviridae family, including Hepatitis C virus (HCV), into cells that are susceptible to virus infection. These compounds are useful for the treatment, therapy and/or prophylaxis of viral diseases and infection, including HCV infection.

Synthesis and insecticidal/acaricidal activity of novel 3-(2,4,6- trisubstituted phenyl)uracil derivatives

A series of novel 3-(2,4,6-trisubstituted phenyl)uracil derivatives has been synthesised and assayed for insecticidal/acaricidal activity. The assay indicated certain requirements for optimal insecticidal activity, which can be summarised as follows: (a) the substituents on the phenyl ring should possess hydrophobicity and electron-withdrawing properties, and the sum of their volumes determines the level of activity; (b) the substituent at the 6- position on the uracil ring should also possess electron-withdrawing properties and hydrophobicity, together with the correct volume; (c) the 1- position on the uracil ring should be unsubstituted for activity against Nephotettix cincticeps and Epilachna vigintioctopunctata, but substituents with length C3 to C4 may be optimal for activity against Tetranychus urticae; (d) certain substituents at the 5-position of the uracil ring give activity against E vigintioctopunctata and T urticae, but not against N cincticeps; (e) a thiocarbonyl group at the 2-position of the uracil ring is less effective than a carbonyl group. Of the compounds assayed, 3-(2,6-dichloro-4- trifluoromethylphenyl)-6-trifluoromethyluracil showed high activity against all the species assayed. (C) 2000 Society of Chemical Industry.