Fmoc-D-Phe(2-Cl)-OH

Name: Fmoc-D-Phe(2-Cl)-OH
Brand: ChemScene
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CAS No. 205526-22-3
Cat. No. CS-W009688
Molecule weight421.87
Purity≥97%
MDL No.MFCD00672547

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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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Structure of 205526-22-3

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General Information

CAS No. 205526-22-3
Cat. No. CS-W009688
Purity ≥97%
MDL No. MFCD00672547
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₄H₂₀ClNO₄
Molecular Weight 421.87
Synonym(s) None
SMILES O=C(N[C@@H](C(O)=O)CC1=CC=CC=C1Cl)OCC2C3=CC=CC=C3C4=CC=CC=C42

Description

Fmoc-D-Phe(2-Cl)-OH features a fluorinated benzene ring at the ortho position, enhancing electronic and steric influence in peptide synthesis. This D-configured amino acid derivative offers improved metabolic stability and resistance to enzymatic degradation. The Fmoc protecting group enables efficient solid-phase coupling under standard conditions.

Application

Fmoc-D-Phe(2-Cl)-OH serves as a key building block in peptide synthesis, enabling the incorporation of D-phenylalanine with a 2-chloro substituent at the aromatic ring. The Fmoc group provides orthogonal protection for amine functionality, allowing efficient sequential coupling under standard solid-phase conditions. The electron-withdrawing chlorine substituent enhances metabolic stability and modulates lipophilicity, making this residue valuable in the design of bioactive peptides and peptidomimetics. Its bench-stable nature and compatibility with common deprotection protocols facilitate reliable synthesis and purification.

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-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

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Computational Chemistry Data

TPSA 75.63
LogP 4.8744
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

Other Classifications

Bioactive Molecules Peptides

Building Blocks Functional Group Fmoc

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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Fmoc-D-Phe(2-Cl)-OH

CAS No. 205526-22-3

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