2145-56-4

Basic information

• Product Name: 5,6-DIHYDRO-5-(TRIFLUOROMETHYL)URACIL
• Synonyms: 5-(TRIFLUOROMETHYL)-5,6-DIHYDROURACIL;5,6-DIHYDRO-5-(TRIFLUOROMETHYL)URACIL;URACIL, (+/-)-5-TRIFLUOROMETHYL-5,6-DIHYDRO-;5-(TRIFLUOROMETHYL-5,6-DIHYDROURACIL, 97% MIN.;5,6-Dihydro-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione;5-(trifluoroMethyl)-1,3-diazinane-2,4-dione;5,6-DIHYDRO-5-(TRIFLUOROMETHYL)URACI;5-(Trifluoromethyl)dihydropyrimidine-2,4(1H,3H)-dione
• CAS NO: 2145-56-4
• Molecular Formula: C₅H₅F₃N₂O₂
• Molecular Weight: 182.1
• Product Categories: Biochemicals and Reagents;Nucleoside Analogs;Nucleosides, Nucleotides, Oligonucleotides
• Mol File: 2145-56-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 205-206 °C
• Boiling Point: Safety Data
  1. N/A
  2. N/A
  3. N/A
  4. 3
  6. N/A
  7. N/A
  8. 2145-56-4(Hazardous Substances Data)
• WGK Germany: 3
• Hazardous Substances Data: 2145-56-4(Hazardous Substances Data)

Usage

Synthesis Reference(s)

Tetrahedron Letters, 23, p. 4099, 1982 DOI: 10.1016/S0040-4039(00)88357-4

InChI:InChI=1/C5H5F3N2O2/c6-5(7,8)2-1-3(11)10-4(12)9-2/h2H,1H2,(H2,9,10,11,12)

Upstream product

• 1514-82-5 2-bromo-3,3,3-trifluoropropene 
• 201230-82-2 carbon monoxide 
• 57-13-6 urea 
• 381-98-6 trifluoromethyacrylic acid 
• 917-61-3 sodium isocyanate 
• 104939-18-6 α-(trifluoromethyl)-β-alanine 

Downstream Products

• 54-20-6 5-trifluoromethyluracil 
• 707-04-0 5-bromo-5-trifluoromethyl-5,6-dihydrouracil 

Relevant articles and documents

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NEW AND DIRECT ROUTE TO 5-TRIFLUOROMETHYL-5,6-DIHYDROURACILS BY MEANS OF PALLADIUM COMPLEX CATALYZED "UREIDOCARBONYLATION" OF 2-BROMO-3,3,3-TRIFLUOROPROPENE

Palladium complex catalyzed carbonylation of 2-bromo-3,3,3-trifluoropropene (2-Br-TFP) with ureas afforded 5-trifluoromethyl-5,6-dihydrouracils in moderate to good yields, which were converted into 5-trifluoromethyluracils in nearly quantitative yields.

Process for Producing 1-(2'-deoxy-beta-D-erythropentofuranosyl)-5-trifluoromethyluracil Derivatives

A process for producing 1-(2'-deoxy-β-D-erythro-pentofuranosyl)-5-trifluoromethyluracil derivative of the formula (3) by which the desired compound can be produced easily at a low cost with high selectivity is disclosed. The process according to the present invention comprises (a) reacting 5-trifluoromethyl-5,6-dihydrouracil with alkylsulfoxide in the presence of a halogen and an acid catalyst to obtain 5-trifluoromethyluracil; (b) reacting the obtained 5-trifluoromethyluracil with a silylating agent to obtain 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine of the formula (1) and (c) reacting the obtained 5-trifluoromethyl-2,4-bis(trimethylsilyloxy)pyrimidine with 2-deoxy-α-D-erythro-pentofuranosyl halide derivative of the formula (2) in chloroform solvent in the presence of fluoride ion and in the presence of a copper compound as a catalyst.

An effective and convenient route to 5-trifluoromethyl-5,6-dihydrouracils and their thio derivatives

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