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

Name: (S)-2-((tert-Butoxycarbonyl)amino)-4,4,4-trifluorobutanoic acid
Brand: ChemScene
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CAS No. 181128-25-6
Cat. No. CS-0226391
Purity≥97%
MDL No.None

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

Structure of 181128-25-6

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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.

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

Computational Chemistry Data

TPSA 75.63
LogP 1.9167
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 3

Safety Information

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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

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Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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

CAS No. 181128-25-6

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