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CS-W001157 4
Total: USD 88.00

6-(Trifluoromethyl)uracil

  • CAS No. 672-45-7

  • Cat. No. CS-W002726
  • Purity≥98%
  • MDL No.MFCD01011762

*For research and further manufacturing use only, not for direct human use.

6-(Trifluoromethyl)uracil|CS-W002726

Structure of 672-45-7

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General Information

  • CAS No. 672-45-7
  • Cat. No. CS-W002726
  • Purity ≥98%
  • MDL No. MFCD01011762
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₃F₃N₂O₂
  • Molecular Weight 180.08
  • Synonym(s) 6-(TRIFLUOROMETHYL)-2,4-(1H,3H)PYRIMIDINEDIONE
  • SMILES O=c1[nH]c(=O)[nH]c(c1)C(F)(F)F

Description

6-(Trifluoromethyl)uracil integrates a strongly electron-withdrawing trifluoromethyl group at the C6 position of the uracil core, enhancing metabolic stability and altering hydrogen-bonding capacity. This modification imparts increased lipophilicity and resistance to enzymatic degradation, making it a valuable scaffold for probing nucleoside analog reactivity and developing targeted antimetabolite agents in medicinal chemistry workflows.

Application

6-(Trifluoromethyl)uracil serves as a valuable building block in medicinal chemistry, enabling the synthesis of fluorinated nucleoside analogs through standard glycosylation protocols. Its trifluoromethyl group enhances metabolic stability and modulates electronic properties, while maintaining compatibility with common protecting group strategies. The compound exhibits good bench stability and facilitates efficient incorporation into heterocyclic scaffolds relevant to antiviral and anticancer research.

Synthesis

  • Route1
    • 2-((4-Hydroxy-6-(trifluoromethyl)pyrimidin-2-yl)thio)acetic acid|CS-0322370
      836-12-4
    • ~%
    • In-stock
      6-(Trifluoromethyl)uracil|CS-W002726
      672-45-7

    References

    • Journal of Organic Chemistry, , vol. 24, p. 113 Journal of the American Chemical Society, , vol. 80, p. 5744,5751
  • Route2
    • 2-Methoxy-6-(trifluoromethyl)pyrimidin-4(1H)-one|CS-0150235
      175354-56-0
    • ~82%
    • In-stock
      6-(Trifluoromethyl)uracil|CS-W002726
      672-45-7

    References

    • Felczak, Krzysztof; Drabikowska, Alicja K.; Vilpo, Juhani A.; Kulikowski, Tadeusz; Shugar, David Journal of Medicinal Chemistry, 1996 , vol. 39, # 8 p. 1720 - 1728
  • Route3
    • null|null
      624-83-9
    • In-stock
      Ethyl 3-amino-4,4,4-trifluorocrotonate|CS-W017064
      372-29-2
    • ~61%
    • In-stock
      6-(Trifluoromethyl)uracil|CS-W002726
      672-45-7

    References

    • Sidduri, Achyutharao; Tilley, Jefferson W.; Lou, Jianping; Tare, Nadine; Cavallo, Gary; Frank, Karl; Pamidimukkala, Anjula; Choi, Duk Soon; Gerber, Louise; Railkar, Aruna; Renzetti, Louis Bioorganic and Medicinal Chemistry Letters, 2013 , vol. 23, # 4 p. 1026 - 1031

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS07
Signal Word : Warning
UN#: N/A
Class : N/A
Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

  • TPSA   65.72
  • LogP   0.082
  • H_Acceptors   2
  • H_Donors   2
  • Rotatable_Bonds   0

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