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CS-W001157 4
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(S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid

  • CAS No. 181128-25-6

  • Cat. No. CS-0226391
  • Molecule weight257.21
  • Purity≥97%
  • MDL No.None

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

(S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid|CS-0226391

Structure of 181128-25-6

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General Information

  • CAS No. 181128-25-6
  • Cat. No. CS-0226391
  • Purity ≥97%
  • MDL No. None
  • Storage 4°C
  • Shipping Room temperature in continental US; may vary elsewhere.
  • Molecular Formula C₉H₁₄F₃NO₄
  • Molecular Weight 257.21
  • Synonym(s) (S)-Boc-2-amino-4,4,4-trifluoro-butyric acid
  • SMILES CC(C)(C)OC(N[C@H](C(O)=O)CC(F)(F)F)=O

Description

(S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid is a chiral building block featuring a trifluoromethylated aliphatic chain and a protected amine. This bench-stable derivative enables straightforward incorporation into peptide backbones and bioactive scaffolds via mild deprotection. The electron-withdrawing trifluoromethyl group enhances metabolic stability and modulates polarity in synthetic intermediates.

Application

(S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid serves as a valuable chiral building block for peptide and peptidomimetic synthesis, leveraging the trifluoromethyl group’s enhanced metabolic stability and lipophilicity. The Boc-protected amine and carboxylic acid functionalities enable straightforward coupling and deprotection sequences, while the α-chiral center supports stereoselective transformations. Its bench-stable nature and compatibility with standard synthetic protocols make it well-suited for medicinal chemistry campaigns requiring fluorinated amino acid analogs.

Synthesis

  • Route1
    • tert-Butyl N-[(2S)-4,4,4-trifluoro-1-hydroxybutan-2-yl]carbamate|CS-0040465
      610272-57-6
    • ~81%
    • In-stock
      (S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid|CS-0226391
      181128-25-6

    References

    • Jiang, Zhong-Xing; Qin, Ying-Ying; Qing, Feng-Ling Journal of Organic Chemistry, 2003 , vol. 68, # 19 p. 7544 - 7547
  • Route2
    • null|null
      610272-56-5
    • ~%
    • In-stock
      (S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid|CS-0226391
      181128-25-6

    References

    • Jiang, Zhong-Xing; Qin, Ying-Ying; Qing, Feng-Ling Journal of Organic Chemistry, 2003 , vol. 68, # 19 p. 7544 - 7547
  • Route3
    • null|null
      610272-53-2
    • ~%
    • In-stock
      (S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid|CS-0226391
      181128-25-6

    References

    • Jiang, Zhong-Xing; Qin, Ying-Ying; Qing, Feng-Ling Journal of Organic Chemistry, 2003 , vol. 68, # 19 p. 7544 - 7547

Safety Information

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

Quality Control

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Computational Chemistry Data

  • TPSA   75.63
  • LogP   1.9167
  • H_Acceptors   3
  • H_Donors   2
  • Rotatable_Bonds   3

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