N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine

Name: N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine
Brand: ChemScene
Availability: InStock
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CAS No. 1223105-51-8
Cat. No. CS-0439186
Purity≥97%
MDL No.MFCD22989428

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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-(S)-2,6-difluoro-α-methylphenylalanine|CS-0439186

Structure of 1223105-51-8

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Description

N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine is a sterically hindered, electron-deficient amino acid derivative designed for peptide synthesis. The α-methyl group confers conformational rigidity, while the ortho-fluorine substituents enhance metabolic stability and modulate electronic properties. This residue integrates seamlessly into challenging sequences, offering improved solubility and resistance to enzymatic degradation under standard coupling conditions.

Application

N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine serves as a valuable building block for the synthesis of bioactive peptides and peptidomimetics. The ortho-difluoro substitution enhances metabolic stability and modulates electronic properties, while the α-methyl group confers conformational rigidity and resistance to proteolytic degradation. The Fmoc protecting group enables efficient solid-phase peptide synthesis with straightforward deprotection under mild basic conditions. This derivative facilitates the incorporation of sterically constrained, electron-deficient aromatic side chains into target scaffolds with high reliability and reproducibility.

General Information

CAS No. 1223105-51-8
Cat. No. CS-0439186
Purity ≥97%
MDL No. MFCD22989428
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₂₅H₂₁F₂NO₄
Molecular Weight 437.44
Synonym(s) (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-3-(2,6-difluorophenyl)-2-methylpropanoic acid
SMILES FC(C=CC=C1F)=C1C[C@](C(O)=O)(C)NC(OCC2C3=CC=CC=C3C4=CC=CC=C42)=O

Computational Chemistry Data

TPSA 75.63
LogP 4.8893
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 6

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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Other Classifications

Building Blocks Functional Group Fluoride

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Phenylalanine and derivatives

Chemical Biology Peptide Chemistry Amine Protection

Chemical Biology Peptide Chemistry Amino Acid Derivatives

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N-Fmoc-(S)-2,6-difluoro-α-methylphenylalanine

CAS No. 1223105-51-8

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