51-65-0

Basic information

• Product Name: DL-3-(4-Fluorophenyl)alanine
• Synonyms: d,l-fluorophenylalanine;H-DL-PHE(P-F)-OH;H-DL-PHE(4-F)-OH;H-P-FLUORO-DL-PHE-OH;DL-4-FLUOROPHENYLALANINE;DL-P-FLUOROPHENYLALANINE;2-AMINO-3-(4-FLUOROPHENYL)PROPIONIC ACID;3-(4-FLUOROPHENYL)-DL-ALANINE
• CAS NO: 51-65-0
• Molecular Formula: C₉H₁₀FNO₂
• Molecular Weight: 183.18
• EINECS: 200-113-7
• Product Categories: Fluorobenzene;Benzenes;A - HPeptide Synthesis;Amino Acids;Modified Amino Acids;Peptide Synthesis;Phenylalanine Derivatives;Unnatural Amino Acid Derivatives;amino
• Mol File: 51-65-0.mol
• Article Data: 7

Chemical Properties

• Melting Point: 253-255 °C (dec.)(lit.)
• Boiling Point: 313.3 °C at 760 mmHg
• Flash Point: 143.3 °C
• Appearance: white powder or flakes
• Density: 1.1939 (estimate)
• Vapor Pressure: 0.000214mmHg at 25°C
• Refractive Index: 1.555
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: pK1:2.13(＋1);pK2:9.05(0) (25°C)
• Water Solubility: slightly soluble
• Stability: Stable. Combustible. Incompatible with strong oxidising agents. May be light sensitive.
• BRN: 29338793
• CAS DataBase Reference: DL-3-(4-Fluorophenyl)alanine(CAS DataBase Reference)
• NIST Chemistry Reference: DL-3-(4-Fluorophenyl)alanine(51-65-0)
• EPA Substance Registry System: DL-3-(4-Fluorophenyl)alanine(51-65-0)

Safety Data

• Hazard Codes: T
• Statements: 25
• Safety Statements: 45
• RIDADR: UN 2811 6.1/PG 3
• WGK Germany: 3
• RTECS: AY6315000
• TSCA: Yes
• PackingGroup: III
• Hazardous Substances Data: 51-65-0(Hazardous Substances Data)

Usage

Chemical Properties

white powder or flakes

Definition

ChEBI: A phenylalanine derivative in which the hydrogen at position 4 on the benzene ring is replaced by a fluoro group.

General Description

White powder or white shiny flakes.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

DL-3-(4-Fluorophenyl)alanine may be sensitive to exposure to light. A fluorinated amino acid. This is a neutral to slightly acidic material. DL-3-(4-Fluorophenyl)alanine may react as an organic amine or acid, although, its reactivity is moderated considerably by the presence of the other group.

Health Hazard

SYMPTOMS: DL-3-(4-Fluorophenyl)alanine is a phenylalanine antagonist and may cause inhibition of protein synthesis.

Fire Hazard

Flash point data for DL-3-(4-Fluorophenyl)alanine are not available; however, DL-3-(4-Fluorophenyl)alanine is probably combustible.

Biochem/physiol Actions

Inhibits mitosis and reversibly arrests HeLa cells in G2.

InChI:InChI=1/C9H10FNO2/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8H,5,11H2,(H,12,13)

Upstream product

• 449-81-0 (4Z)-2-phenyl-4-[(4-fluorophenyl)methylidene]-1,3-oxazol-5(4H)-one 
• 138996-53-9 (Z)-ethyl 2-benzamido-3-(4-fluorophenyl)acrylate 
• 459-32-5 4-fluorocinnamic acid 
• 459-32-5 (E)-4-fluorocinnamic acid 
• 1132-68-9 L-4-fluorophenylalanine 
• 1353886-54-0 ethyl 3-(4-fluorophenyl)-2-(hydroxyimino)propanoate 
• 80980-62-7 (+/-)-15-aminomethyl-14-hydroxy-5,5-dimethyl-2,8-dithia<9>(2,5)pyridophane 
• 1994-30-5 Sodium; 3-(4-fluoro-phenyl)-2-oxo-propionate 
• 587-76-8 α-benzoylamino-4-fluoro-cinnamic acid 
• 17481-06-0 rac-Ac-p-F-Phe-OH 
• 380-71-2 diethyl α-acetamido, α-(4-fluorobenzyl)malonate 

Downstream Products

• 39801-54-2 N-(trifluoroacetyl)-p-fluoro-DL-phenylalanine 
• 59850-77-0 ethyl 2-amino-3-(4-fluorophenyl) propanoate 
• 153889-27-1 N-phthaloyl-DL-(4-fluorophenyl)alanine 
• 129101-25-3 2-(R)-tert-butoxycarbonylamino-3-(4-fluorophenyl)-propionic acid 
• 1114547-60-2 N-(3-chloro-4-cyanophenyl)-4-fluorophenylalanine 
• 123286-12-4 Boc-DL-(p-fluoro)Phe-NH₂ 

Relevant articles and documents

Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines

The conversion of carboxylic acids, such as acrylic acids, to amines is a transformation that remains challenging in synthetic organic chemistry. Despite the ubiquity of similar moieties in natural metabolic pathways, biocatalytic routes seem to have been overlooked for this purpose. Herein we present the conception and optimisation of a two-enzyme system, allowing the synthesis of β-phenylethylamine derivatives from readily-available ring-substituted cinnamic acids. After characterisation of both parts of the reaction in a two-step approach, a set of conditions allowing the one-pot biotransformation was optimised. This combination of a reversible deaminating and irreversible decarboxylating enzyme, both specific for the amino acid intermediate in tandem, represents a general method by which new strategies for the conversion of carboxylic acids to amines could be designed.

ANTIBACTERIALS AND/OR MODULATORS OF BIOFILM FORMATION AND METHODS OF USING THE SAME

Amides substituted with aromatic groups were synthesized and some were purified to create enantiomer pure compounds. The compounds were tested to determine their ability to inhibit the growth of bacteria and the formation of biofilms created by bacteria. Some of these compounds were found to be effective antibacterials and to effectively inhibit the formation of biofilms.

Immunomodulatory peptides

The invention relates to peptides derivatized with a hydrophilic polymer which, in some embodiments, bind to human FcRn and inhibit binding of the Fc portion of an IgG to an FcRn, thereby modulating serum IgG levels. The disclosed compositions and methods may be used in some embodiments, for example, in treating autoimmune diseases and inflammatory disorders. The invention also relates, in further embodiments, to methods of using and methods of making the peptides of the invention.