5-(Trifluoromethyl)uracil

Base Information

• Chemical Name: 5-(Trifluoromethyl)uracil
• CAS No.: 54-20-6
• Molecular Formula: C5H3F3N2O2
• Molecular Weight: 180.086
• Hs Code.: 29335990
• European Community (EC) Number: 200-197-5
• NSC Number: 73757
• UNII: 4U846R5P34
• DSSTox Substance ID: DTXSID40202304
• Nikkaji Number: J49.057A
• Wikidata: Q27260511
• ChEMBL ID: CHEMBL405942
• Mol file: 54-20-6.mol

Synonyms:5-TFMU;trifluoromethyluracil

Chemical Property of 5-(Trifluoromethyl)uracil

Chemical Property:

• Appearance/Colour: white to faintly yellow crystalline powder
• Melting Point: 245-246 °C(lit.)
• Refractive Index: 1.427
• Boiling Point: 350oC
• PKA: 6.63±0.10(Predicted)
• PSA: 65.72000
• Density: 1.554 g/cm³
• LogP: 0.08200
• Storage Temp.: −20°C
• Solubility.: methanol: soluble50mg/mL, clear
• Water Solubility.: INSOLUBLE
• XLogP3: 0
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 0
• Exact Mass: 180.01466183
• Heavy Atom Count: 12
• Complexity: 268

Purity/Quality:

99.5%+ ^*data from raw suppliers

Trifluorothymine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi,T
• Statements: 22-36/38-40-36/37/38-25
• Safety Statements: 24/25-36-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=C(C(=O)NC(=O)N1)C(F)(F)F

Technology Process of 5-(Trifluoromethyl)uracil

There total 22 articles about 5-(Trifluoromethyl)uracil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

iodotrifluoromethane (2314-97-8,263005-66-9) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 5-trifluoromethyluracil (54-20-6)

Guidance literature:

With iron(III) sulfate; dihydrogen peroxide; In water; dimethyl sulfoxide; at 40 - 50 ℃; for 0.333333h; Product distribution / selectivity;

Reference yield: 91.9%

Langlois reagent (2926-29-6) + uracil (66-22-8,144104-68-7,18324-22-6,27072-01-1,2920-92-5,51953-19-6) → 5-trifluoromethyluracil (54-20-6)

Guidance literature:

With sodium persulfate; copper(II) sulfate; In water; at 60 - 65 ℃; for 6h; Temperature; Reagent/catalyst;

Reference yield: 91.0%

2,4-difluoro-5-trifluoromethyl-pyrimidine (153600-17-0) → 5-trifluoromethyluracil (54-20-6)

Guidance literature:

With potassium fluoride; at 50 ℃; for 5h;

DOI:10.1016/0022-1139(95)03386-6

upstream raw materials:

N¹,N³-dibenzyloxymethyl-5-(trifluoromethyl)uracil

Bromotrifluoromethane

uracil

bis(trifluoromethyl)mercury

Downstream raw materials:

(Z)-1-(2-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidene)ethyl)-5-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione

1-(3,5-di-O-benzoyl-β-L-xylo-furanosyl)-5-(trifluoromethyl)uracil

5-(trifluoromethyl)uridine

2,4-dibromo-5-(trifluoromethyl)pyrimidine