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CS-W001157 4
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Dimethyl 2-fluoromalonate

  • CAS No. 344-14-9

  • Cat. No. CS-0020165
  • Purity≥97%
  • MDL No.MFCD00054680

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

Dimethyl 2-fluoromalonate|CS-0020165

Structure of 344-14-9

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General Information

  • CAS No. 344-14-9
  • Cat. No. CS-0020165
  • Purity ≥97%
  • MDL No. MFCD00054680
  • Storage Store at room temperature
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₅H₇FO₄
  • Molecular Weight 150.11
  • Synonym(s) Fluoromalonic acid dimethyl ester
  • SMILES O=C(OC)C(F)C(OC)=O

Description

Dimethyl 2-fluoromalonate features a fluorinated malonate core with enhanced electrophilicity at the α-carbon, enabling efficient C–C bond formation in nucleophilic addition reactions. This bench-stable reagent integrates readily into synthetic sequences requiring activated ester equivalents, offering high functional group tolerance and predictable regioselectivity under mild conditions.

Application

Dimethyl 2-fluoromalonate serves as a versatile building block in synthetic organic chemistry, enabling the efficient construction of fluorinated carbocycles and heterocycles via Michael additions, Mannich reactions, and cycloadditions. Its electrophilic fluorine enhances reactivity in nucleophilic substitution processes, while the malonate ester functionality supports facile deprotonation and subsequent functionalization. The compound exhibits good bench stability and is compatible with a range of protecting group strategies, facilitating its use in medicinal chemistry lead optimization and process-scale synthesis.

Synthesis

  • Route1

    References

    • Xu, Ze-Qi; DesMarteau, Daryl D.; Gotoh, Yoshihiko Journal of Fluorine Chemistry, 1992 , vol. 58, # 1 p. 71 - 79
  • Route2
    • null|null
      78948-09-1
    • null|null
      18424-76-5
    • ~56%
    • In-stock
      Dimethyl 2-fluoromalonate|CS-0020165
      344-14-9

    References

    • Lerman, Ori; Rozen, Shlomo Journal of Organic Chemistry, 1983 , vol. 48, # 5 p. 724 - 727
  • Route3
    • null|null
      67-56-1
    • null|null
      120131-06-8
    • ~55%
    • In-stock
      Dimethyl 2-fluoromalonate|CS-0020165
      344-14-9

    References

    • Molines, Huguette; Wakselman, Claude Journal of Organic Chemistry, 1989 , vol. 54, # 23 p. 5618 - 5620

Safety Information

Download SDS
GHS Pictogram :
GHS No : GHS05
Signal Word : Danger
UN#: 3265
Class : 8
Packing Group : Ⅱ
Hazard Statements : H314-H318
Precautionary Statements : P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P363-P405-P501

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Computational Chemistry Data

  • TPSA   52.6
  • LogP   -0.3295
  • H_Acceptors   4
  • H_Donors   0
  • Rotatable_Bonds   2

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