N-Fmoc-2,5-difluoro-L-phenylalanine

Name: N-Fmoc-2,5-difluoro-L-phenylalanine
Brand: ChemScene
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CAS No. 1004959-90-3
Cat. No. CS-0158519
Purity≥98%
MDL No.MFCD07372004

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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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N-Fmoc-2,5-difluoro-L-phenylalanine|CS-0158519

Structure of 1004959-90-3

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General Information

CAS No. 1004959-90-3
Cat. No. CS-0158519
Purity ≥98%
MDL No. MFCD07372004
Storage Store at room temperature
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₁₉F₂NO₄
Molecular Weight 423.41
Synonym(s) Fmoc-L-2,5-Difluorophenylalanine
SMILES C([C@@H](NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)CC=4C(=CC=C(C4)F)F)(=O)O

Description

N-Fmoc-2,5-difluoro-L-phenylalanine integrates a fluorinated aromatic side chain with a bench-stable Fmoc protecting group, enabling efficient incorporation into peptide chains under standard coupling conditions. The para-fluorine substitution enhances metabolic stability and modulates electronic properties, while the ortho-fluorines introduce steric and conformational constraints beneficial for structural studies. This derivative supports the synthesis of bioactive peptides requiring enhanced membrane permeability and resistance to enzymatic degradation.

Application

N-Fmoc-2,5-difluoro-L-phenylalanine serves as a valuable building block in peptide synthesis, enabling the incorporation of ortho-fluorinated aromatic side chains with enhanced metabolic stability and modulated electronic properties. The Fmoc group provides excellent protection for the α-amino function, allowing for straightforward deprotection under standard conditions. Its difluorophenyl moiety offers improved lipophilicity and resistance to oxidative metabolism, making it particularly useful in medicinal chemistry campaigns targeting bioactive peptides and peptidomimetics.

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 : H302-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P363-P501

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Computational Chemistry Data

TPSA 75.63
LogP 4.4992
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Building Blocks Functional Group Fmoc

Building Blocks Functional Group Fluoride

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

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N-Fmoc-2,5-difluoro-L-phenylalanine

CAS No. 1004959-90-3

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