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CS-W001157 4
Total: USD 88.00

6-(Hydroxymethyl)uracil

  • CAS No. 22126-44-9

  • Cat. No. CS-M2299
  • Molecule weight142.11
  • Purity≥98%
  • MDL No.MFCD00797681

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

6-(Hydroxymethyl)uracil|CS-M2299

Structure of 22126-44-9

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General Information

  • CAS No. 22126-44-9
  • Cat. No. CS-M2299
  • Purity ≥98%
  • MDL No. MFCD00797681
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₆N₂O₃
  • Molecular Weight 142.11
  • Synonym(s) NSC 104987; NSC 253551; 2,4(1H,3H)-Pyrimidinedione,6-(hydroxymethyl)
  • SMILES O=C1NC(C=C(CO)N1)=O

Description

6-(Hydroxymethyl)uracil features a hydroxymethyl group appended to the C6 position of the uracil core, enhancing solubility and enabling site-specific conjugation in nucleic acid chemistry. This functionalized analog serves as a key building block for modified oligonucleotides, offering improved stability and compatibility with enzymatic synthesis workflows.

Application

6-(Hydroxymethyl)uracil serves as a versatile uracil derivative enabling site-specific modifications in nucleoside and nucleotide synthesis. Its hydroxymethyl group facilitates efficient functionalization via oxidation to carboxylic acid or conversion to aldehyde handles, supporting conjugation strategies. The compound exhibits good bench stability and compatibility with standard protecting group protocols, making it a reliable building block for carbohydrate- and peptide-nucleic acid hybrid architectures.

Synthesis

  • Route1
    • 2,6-Dihydroxypyrimidine-4-carbaldehyde|CS-0451679
      36327-91-0
    • ~95%
    • In-stock
      6-(Hydroxymethyl)uracil|CS-M2299
      22126-44-9

    References

    • Zhao, Cen; Pelaez, Miguel; Dionysiou, Dionysios D.; Pillai, Suresh C.; Byrne, John A.; O'Shea, Kevin E. Catalysis Today, 2014 , vol. 224, p. 70 - 76
  • Route2
    • 6-(Hydroxymethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one|CS-0594460
      31555-11-0
    • ~%
    • In-stock
      6-(Hydroxymethyl)uracil|CS-M2299
      22126-44-9

    References

    • Johnson; Schroeder Journal of the American Chemical Society, 1932 , vol. 54, p. 2941,2942
  • Route3
    • 6-Oxo-2-thioxo-1,2,3,6-tetrahydropyrimidine-4-carbaldehyde|CS-0701220
      16953-46-1
    • ~%
    • In-stock
      6-(Hydroxymethyl)uracil|CS-M2299
      22126-44-9

    References

    • Johnson; Schroeder Journal of the American Chemical Society, 1932 , vol. 54, p. 2941,2942

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-P280-P302+P352

Quality Control

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Computational Chemistry Data

  • TPSA   85.95
  • LogP   -1.4445
  • H_Acceptors   3
  • H_Donors   3
  • Rotatable_Bonds   1

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