(S)-2-Amino-4,4,4-trifluorobutanoic acid

Name: (S)-2-Amino-4,4,4-trifluorobutanoic acid
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CAS No. 15960-05-1
Cat. No. CS-0119487
Molecule weight157.09
Purity≥98%
MDL No.MFCD31537561

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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(S)-2-Amino-4,4,4-trifluorobutanoic acid|CS-0119487

Structure of 15960-05-1

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General Information

CAS No. 15960-05-1
Cat. No. CS-0119487
Purity ≥98%
MDL No. MFCD31537561
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₄H₆F₃NO₂
Molecular Weight 157.09
Synonym(s) (2S)-2-Amino-4,4,4-trifluorobutanoic acid
SMILES [C@H](CC(F)(F)F)(C(O)=O)N

Description

(S)-2-Amino-4,4,4-trifluorobutanoic acid features a chiral α-amino acid scaffold with a trifluoromethyl group at the γ-position, imparting enhanced metabolic stability and altered electronic properties. This configuration delivers a potent bioisostere for glutamic acid, enabling precise incorporation into peptidomimetics and enzyme substrates where modulated polarity and conformational rigidity are critical.

Application

(S)-2-Amino-4,4,4-trifluorobutanoic acid serves as a valuable chiral building block for the synthesis of bioactive molecules, particularly in medicinal chemistry and peptide-based drug discovery. The trifluoromethyl group imparts enhanced metabolic stability and membrane permeability, while the amino and carboxylic acid functionalities enable straightforward derivatization via amide bond formation or incorporation into peptidomimetics. Its bench-stable solid form facilitates handling and purification, making it well-suited for scalable synthetic workflows.

Synthesis

Route1
- 120097-65-6
- ~94%
- 15960-05-1
References
- Tsushima; Kawada; Ishihara; Uchida; Shiratori; Higaki; Hirata Tetrahedron, 1988 , vol. 44, # 17 p. 5375 - 5387
Route2
- 15960-04-0
- ~%
- 15960-05-1
References
- Angewandte Chemie, , vol. 79, # 17/18 p. 822 - 823

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+P364-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 63.32
LogP 0.3507
H_Acceptors 2
H_Donors 2
Rotatable_Bonds 2

Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Alanine and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-2-Amino-4,4,4-trifluorobutanoic acid

CAS No. 15960-05-1

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