169243-86-1

Basic information

• Product Name: FMOC-L-4-Fluorophe
• Synonyms: N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-4-FLUORO-PHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-4-FLUORO-L-PHENYLALANINE;N-ALPHA-FMOC-4-FLUORO-L-PHENYLALANINE;(S)-N-FMOC-4-FLUOROPHENYLALANINE;(S)-FMOC-4-FLUORO-PHENYLALANINE;RARECHEM BK PT 0033;(S)-2-(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)-3-(4-FLUORO-PHENYL)-PROPIONIC ACID;L-4-Fluorophenylalanine, N-FMOC protected
• CAS NO: 169243-86-1
• Molecular Formula: C24H20FNO4
• Molecular Weight: 405.42
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;Phenylalanine [Phe, F];Unusual Amino Acids;Fmoc-Amino acid series;a-amino
• Mol File: 169243-86-1.mol
• Article Data: 6

Chemical Properties

• Melting Point: 185.4 °C
• Boiling Point: 623.9 °C at 760 mmHg
• Flash Point: 331.1 °C
• Appearance: white fluffy powder
• Density: 1.2642 (estimate)
• Vapor Pressure: 1.99E-16mmHg at 25°C
• Storage Temp.: 2-8°C
• Solubility: Soluble in Dimethylformamide(DMF).
• PKA: 3.75±0.10(Predicted)
• BRN: 8287377
• CAS DataBase Reference: FMOC-L-4-Fluorophe(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-L-4-Fluorophe(169243-86-1)
• EPA Substance Registry System: FMOC-L-4-Fluorophe(169243-86-1)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25-22-28-26
• WGK Germany: WGK 2 water endangering
• Hazardous Substances Data: 169243-86-1(Hazardous Substances Data)

Usage

Description

FMOC-L-4-Fluorophe, also known as 4-Fluoro-N-Fmoc-L-phenylalanine, is a phenylalanine derivative characterized by its white fluffy powder appearance. It is a key component in the synthesis of various pharmaceutical compounds and has been introduced in collaboration with Yu and coworkers, reflecting a methodology reported in C-H Activation.

Uses

Used in Pharmaceutical Industry:
FMOC-L-4-Fluorophe is used as a pharmaceutical intermediate for the synthesis of various pharmaceutical compounds. Its unique chemical properties and reactivity make it a valuable building block in the development of new drugs and therapeutic agents.
Used in C-H Activation Methodology:
FMOC-L-4-Fluorophe has been introduced in collaboration with Yu and coworkers as a part of the C-H Activation methodology. This innovative approach allows for the efficient and selective functionalization of organic compounds, paving the way for the development of new synthetic routes and applications in the field of organic chemistry.

InChI:InChI=1/C24H20FNO4/c25-16-11-9-15(10-12-16)13-22(23(27)28)26-24(29)30-14-21-19-7-3-1-5-17(19)18-6-2-4-8-20(18)21/h1-12,21-22H,13-14H2,(H,26,29)(H,27,28)/p-1/t22-/m0/s1

Upstream product

• 51-65-0 4-Fluorophenylalanine 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 1132-68-9 L-4-fluorophenylalanine 
• 17543-58-7 2S-2-benzyloxycarbonylamino-2-(4-fluorophenylmethyl)-acetic acid 
• 141971-11-1 Z-DL-Phe(4F)OMe 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 73283-54-2 (S)-methyl 2-amino-3-(4-fluorophenyl)propanoate 
• 352-34-1 4-fluoro-1-iodobenzene 

Downstream Products

• 1213773-17-1 O-W-F-F(4-F)-F-H(1-Bzl)-NH₂ 
• 1213772-53-2 O-F(4-F)-F-I-F-H(1-Bzl)-NH₂ 
• 1213772-85-0 O-W-F(4-F)-I-F-H(1-Bzl)-NH₂ 
• 1213773-49-9 O-W-F-I-F(4-F)-H(1-Bzl)-NH₂ 

Relevant articles and documents

METHOD FOR PREPARING AROMATIC AMINO ACID DERIVATIVE

The present invention provides methods of efficiently producing various optically active aromatic amino acid derivatives by reacting, using an additive, a specific ester compound with an aromatic halide and zinc in the presence of a catalyst. The present invention also provides amino acid derivatives that can be produced by the methods.

LIGAND-CONTROLLED C(SP3)-H ARYLATION AND OLEFINATION IN SYNTHESIS OF UNNATURAL CHIRAL ALPHA AMINO ACIDS

The use of ligands to tune the reactivity and selectivity of transition metal-catalysts for C(-sp3)-H bond functionalization is a central challenge in synthetic organic chemistry. Herein, we report a rare example of catalyst-controlled C(sp3)-H arylation using pyridine and quinoline derivatives: the former promotes exclusive monoarylation, whereas the latter activates the catalyst further to achieve diarylation. Successive application of these ligands enables the sequential diarylation of a methyl group in an alanine derivative with two different aryl iodides, affording a wide range of β-Ar-p-Ar ' -cc-amino acids with excellent levels of diastereoselectivity (d.r. > 20:1). Both configurations of the β-chiral center can be accessed by choosing the order in which the aryl groups are installed. The use of a quinoline derivative as a ligand also enables C(sp3)-H olefination of a protected alanine.

Solid phase β-lactams synthesis using the Staudinger reaction, monitored by 19F NMR spectroscopy

We report the use of 19F NMR as a simple means to monitor reactions on a solid phase. Multi-step sequences including protection, coupling, deprotection, condensation, cycloaddition and cleavage steps are described in the case of multicomponent reactions involving fluorinated α-aminoesters, aldehydes and acid chlorides.