33787-05-2

Basic information

• Product Name: DL-2,6-DIFLUOROPHENYLALANINE
• Synonyms: 2,6-DIFLUOROPHENYLALANINE;2,6-DIFLUORO-DL-PHENYLALANINE;2,6-DIFLUORO-L-PHENYLALANINE;2-AMINO-3-(2,6-DIFLUORO-PHENYL)-PROPIONIC ACID;L-2,6-DIFLUOROPHENYL-ALANINE;DL-2,6-DIFLUOROPHENYLALANINE;H-2,6-DIFLUORO-PHE-OH HCL;(S)-2-AMINO-3-(2,6-DIFLUORO-PHENYL)-PROPIONIC ACID
• CAS NO: 33787-05-2
• Molecular Formula: C₉H₉F₂NO₂
• Molecular Weight: 201.17
• Product Categories: Amino Acid Derivatives
• Mol File: 33787-05-2.mol

Chemical Properties

• Melting Point: 256 °C
• Boiling Point: 301.1°Cat760mmHg
• Flash Point: 135.9°C
• Appearance: /
• Density: 1.379g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• PKA: 2.20±0.10(Predicted)
• CAS DataBase Reference: DL-2,6-DIFLUOROPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: DL-2,6-DIFLUOROPHENYLALANINE(33787-05-2)
• EPA Substance Registry System: DL-2,6-DIFLUOROPHENYLALANINE(33787-05-2)

Safety Data

• Hazardous Substances Data: 33787-05-2(Hazardous Substances Data)

Usage

Uses

L-2,6-Difluorophenylalanine

Upstream product

• 266360-50-3 2-acetylamino-3-(2,6-difluoro-phenyl)-propionic acid 
• 152152-09-5 (E)-2,6-difluorocinnamic acid 
• 85118-00-9 2,6-Difluorobenzyl bromide 
• 266360-45-6 diethyl α-acetamido, α-(2,6-difluorobenzyl)malonate 
• 627910-22-9 (2S)-2-benzyloxycarbonylamino-3-(2,6-difluorophenyl)propionic acid 
• 710350-50-8 (3S,5S,6R)-3-(2,6-difluorophenylmethyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazine-2-one 

Downstream Products

• 167993-07-9 N-{[(1,1-dimethylethyl)oxy]carbonyl}-2,6-difluoro-L-phenylalanine 
• 1235020-13-9 N-{[(9H-fluoren-9-yl)methoxy]carbonyl}-2,6-difluoro-L-phenylalanine 

Relevant articles and documents

HALOALKYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

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HALOALKYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

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HALOALKYL CONTAINING COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

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AMIDINO COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceu

CYSTEINE PROTEASE INHIBITORS

The present invention is directed to compounds that are inhibitors of cysteine protease, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceut

PEPTIDIC COMPOUNDS AS CYSTEINE PROTEASE INHIBITORS

The present invention is directed to compounds that are inhibitors of cysteine proteases, in particular, cathepsins B, K, L, F, and S and are therefore useful in treating diseases mediated by these proteases. The present invention is directed to pharmaceutical compositions comprising these compounds and processes for preparing them.

Synthesis of a complete set of L-difluorophenylalanines, L-(F2)Phe, as molecular explorers for the CH/π interaction between peptide ligand and receptor

A complete set of difluorophenylalanines in the L-configuration [L- (F2)Phe] (namely, L-(2,3-F2)Phe, L-(2,4-F2)Phe, L-(2,5-F2)Phe, L-(2,6- F2)Phe, L-(3,4-F2)Phe, L-(3,5-F2)Phe) w

Phenylalanine ammonia-lyase: The use of its broad substrate specificity for mechanistic investigations and biocatalysis - Synthesis of L-arylalanines

Several fluoro-and chlorophenylalanines were found to be good substrates of phenylalanine ammonialyase (PAL/EC 4.3.1.5) from parsley. The enantiomerically pure L-amino acids were obtained in good yields by reaction of the corresponding cinnamic acids with 5M ammonia solution (buffered to pH 10) in the presence of PAL. The kinetic constants for nine different fluoro-and chlorophenylalanines do not provide a rigorous proof for but are consistent with the previously proposed mechanism comprising an electrophilic attack of the methylidene-imidazolone cofactor of PAL at the aromatic nucleus as a first chemical step. In the resulting Friedel-Crafts-type σ complex the β-protons are activated for abstraction and consequently the pro-S is abstracted by an enzymic base. Results from semi-empirical calculations combined with a proposed partial active site model showed a correlation between the experimental kinetic constants and the change in polarization of the pro-S Cβ-H bond and heat of formation of the σ complexes, thus making the electrophilic attack at the neutral aromatic ring plausible. Furthermore, while 5-pyrimidinylalanine was found to be a moderately good substrate of PAL, 2-pyrimidinylalanine was an inhibitor.