23635-30-5

Basic information

• Product Name: TFA-PHE-OME
• Synonyms: Trifluoroacetyzl L-phenylalanine methyl ester;Alanine, 3-phenyl-N-(trifluoroacetyl)-, methyl ester;Alanine, 3-phenyl-N-(trifluoroacetyl)-, methyl ester, L-;L-Phenylalanine, N-(trifluoroacetyl)-, methyl ester;Methyl 3-phenyl-2-[(trifluoroacetyl)amino]propanoate;N-ALPHA-TRIFLUOROACETYL-L-PHENYLALANINE METHYL ESTER;N-TRIFLUOROACETYL-L-PHENYLALANINE METHYL ESTER;N-TFA-L-PHENYLALANINE METHYL ESTER
• CAS NO: 23635-30-5
• Molecular Formula: C₁₂H₁₂F₃NO₃
• Molecular Weight: 275.22
• Product Categories: I - Z;Modified Amino Acids;Amino Acids
• Mol File: 23635-30-5.mol

Chemical Properties

• Melting Point: 50-52 °C
• Boiling Point: 346.6°C at 760 mmHg
• Flash Point: 163.4°C
• Appearance: /
• Density: 1.283g/cm³
• Vapor Pressure: 5.71E-05mmHg at 25°C
• Refractive Index: 1.472
• Storage Temp.: 2-8°C
• PKA: 9.67±0.46(Predicted)
• CAS DataBase Reference: TFA-PHE-OME(CAS DataBase Reference)
• NIST Chemistry Reference: TFA-PHE-OME(23635-30-5)
• EPA Substance Registry System: TFA-PHE-OME(23635-30-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 23635-30-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Development:
TFA-PHE-OME is used as a building block for peptide synthesis, facilitating the creation of novel peptide-based drugs with potential therapeutic applications.
Used in Chemical Research:
TFA-PHE-OME serves as a model compound for studying the behavior and interactions of amino acids within biological systems, providing insights into their role in various biochemical processes.
Used in Drug Molecule Development:
It is utilized in the development of new drug molecules, contributing to the discovery of innovative therapeutic agents with improved efficacy and selectivity.
Used in Peptide and Protein Structure and Function Studies:
TFA-PHE-OME is employed in the study of peptide and protein structure and function, aiding in the understanding of their roles in biological systems and the design of targeted therapies.

InChI:InChI=1/C12H12F3NO3/c1-19-10(17)9(16-11(18)12(13,14)15)7-8-5-3-2-4-6-8/h2-6,9H,7H2,1H3,(H,16,18)

Upstream product

• 67-56-1 methanol 
• 431-47-0 trifluoroacetic acid-methyl ester 
• 63-91-2 L-phenylalanine 
• 350-09-4 N-trifluoroacetyl-L-phenylalanine 
• 74-88-4 methyl iodide 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 407-25-0 trifluoroacetic anhydride 
• 2563-33-9 N-trifluoroacetyl-L-phenylalanine ethyl ester 
• 16417-60-0 ethyl N-(trifluoroacetyl)-2-amino-3-phenylpropanoate 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 55740-07-3 (4S)-4-benzyl-5-oxo-1,3-oxazolidine-3-carboxylic acid benzyl ester 
• 16480-57-2 L-phenylalanine sodium salt 
• 383-63-1 ethyl trifluoroacetate, 
• 35909-92-3 N-carbobenzoxy-L-phenylalanine methyl ester 

Downstream Products

• 2563-33-9 N-trifluoroacetyl-L-phenylalanine ethyl ester 
• 934672-78-3 (S)-methyl-2-(2,2,2-trifluoroacetamido)-3-(2-iodophenyl)propanoate 
• 170918-41-9 (S)-2-amino-3-phenyl-1,1-dimethylpropanol 
• 91824-56-5 2-(N,N'-Dicarboethoxy-hydrazo)-pentan 
• 96760-73-5 (trifluoroacetyl)-p-nitro-L-phenylalanine methyl ester 
• 104504-45-2 p-Benzoyl-DL-Phenylalanine 

Relevant articles and documents

Synthesis and study of 2-acetyl amino-3-[4-(2-amino-5-sulfo-phenylazo)- phenyl]-propionic acid: A new class of inhibitor for hen egg white lysozyme amyloidogenesis

The compounds capable of blocking the aggregation of amyloidogenic proteins may have therapeutic potentials. We report on the synthesis of 2-acetyl amino-3-[4-(2-amino-5-sulfo-phenylazo)-phenyl]-propionic acid as an HEWL (hen egg white lysozyme) amyloid inhibitor starting from phenylalanine. The compounds arrest the monomers and exhibit anti-aggregating activity. Moreover, the acetyl derivative 1 served as a better inhibitor than the trifluoroacetyl derivative 2 against in vitro amyloid fibrillogenesis of the HEWL model system.

Direct ortho iodination of β- and γ-aryl alkylamine derivatives

Two in one! A trifluoroacetamide protecting group not only masks an amine functionality, but also mimics peptidyl directing effects as a controlling unit in an efficient ortho iodination of a variety of biologically relevant small molecules (see example). (Chemical Equation Presented).

Biotransformations in low-boiling hydrofluorocarbon solvents

Solvent solutions: Low-boiling hydrofluorocarbons (see examples) are excellent solvents for lipase-catalyzed reactions and ideal replacements for conventional organic solvents and supercritical fluids as media for nonaqueous biotransformations. Notably increased rates, yields, and enantioselectivities were observed with the model kinetic resolution of (±)-1-phenylethanol and the desymmetrization of weso-2-cyclopentene-1 ,4-diol.

Use of N-trifluoroacetyl-protected amino acid chlorides in peptide coupling reactions with virtually complete preservation of stereochemistry

The use of protected amino acid chlorides for peptide coupling reactions has long been avoided due to the extensive racemization that commonly occurs during either the acid chloride formation or the coupling reaction itself. Conditions are described which

Mild regeneration of the carboxylic group of amino acid alkyl esters by aqueous methanolic sodium hydrogen carbonate via 5-oxazolidinones

A simple racemization-free procedure allows the regeneration of the carboxylic acid group of amino acid alkyl esters by way of an intermediate 5-oxazolidinone which is hydrolyzed by treatment with sodium hydrogen carbonate in aqueous methanol.

The enzyme-catalysed stereoselective transesterification of phenylalanine derivatives in supercritical carbon dioxide

The subtilisin Carlsberg catalysed transesterification of N-acetyl phenylalanine methyl ester (1), N-acetyl phenylalanine ethyl ester (2), N-trifluoroacetyl phenylalanine methyl ester (3) and N-trifluoroacetyl phenylalanine ethyl ester (4) was studied in supercritical carbon dioxide. The water content of the reaction affects the reactivity of the system; for the transesterification of the methyl esters with ethanol the optimum concentration of water was determined to be about 0.74 M, while for the transesterification of the ethyl esters with methanol the optimum concentration of water was about 1.3 M. The conversion is also dependent upon the concentration of alcohol; for ethanol, 2% v/v gives the maximum conversion, whilst for methanol, only 0.8-1. 2% v/v is required. This is probably due to a difference in the solubility of the substrates in the two alcohol/supercritical carbon dioxide mixtures. The reaction is highly stereoselective, in all cases no evidence for reaction of the D-isomer could be detected by chiral gas chromatography.

Asymmetric Bis(alkoxycarbonylation) Reaction of Homoallylic Alcohols Catalyzed by Palladium in the Presence of Cu(I) Triflate Using the Chiral Bioxazoline Ligand

Palladium-catalyzed asymmetric intra- and intermolecular bis(alkoxycarbonylation) reactions of homoallylic alcohols in the presence of copper(I) triflate were achieved by using the chiral bioxazoline ligand, (S,S)-4,4′-dibenzyl-4,4′,5,5′-tetrahydro-2,2′-bioxazole, under normal pressure of carbon monoxide and oxygen at 25°C to give the corresponding optically active γ-butyrolactones in 19 - 65% ee.

Chiral Recognition of Amino Acid Derivatives: An NMR Investigation of the Selector and the Diastereomeric Complexes

A tetraamidic selector containing two chiral synthons ((S)-phenylalanine) spaced by a 3,6,9-oxadecanoyl bridge (Phe-3-O-TA) (1) was used as stationary phase in capillary GC to perform chiral resolution of N-TFA-amino esters.In this paper we report an investigation on the mechanism of chiral recognition by NMR spectroscopy (1D and 2D, COSY, NOESY, and J-resolved experiments and 13C relaxation times).First the conformation of the selector in CDCl3 and CD3OD was studied to evaluate the structural features that might justify the enantiomeric discrimination ability.Thenthe self-associations of the selector and of the enantiomers (S)- and (R)-methyl (2a,2b) and (S)- and (R)-n-butyl N-TFA-phenylalaninate (3a, 3b) were investigated at variable temperature and concentration in CDCl3.Finally, titration experiments were carried out to detect the sites of the binding interactions between the selector and the enantiomers.A simple recognition mode is proposed to account for both the enantioselectivity of the phase and the elution order of the enantiomers observed in GC (t'RS).This is the first spectroscopic study on the mechanism of chiral recognition in GC concerning the real phase and not a model system.