111119-36-9

Basic information

• Product Name: L-2,4-DICHLOROPHENYLALANINE
• Synonyms: L-2,4-DICHLOROPHE;L-2,4-DICHLOROPHENYLALANINE;H-PHE(2,4-CL 2)-OH;H-PHE(2,4-DICL)-OH;H-L-PHE(2,4-CL2)-OH;RARECHEM BK PT 0109;(S)-2-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID;2,4-Dichloro-L-4-phenylalanine
• CAS NO: 111119-36-9
• Molecular Formula: C₉H₉Cl₂NO₂
• Molecular Weight: 234.08
• Product Categories: Amino Acids;Phenylalanine analogs and other aromatic alpha amino acids;a-amino
• Mol File: 111119-36-9.mol
• Article Data: 3

Chemical Properties

• Melting Point: 238-240 °C
• Boiling Point: 368.1 °C at 760 mmHg
• Flash Point: 176.4 °C
• Appearance: /
• Density: 1.45 g/cm³
• Vapor Pressure: 4.55E-06mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Store at 0-5°C
• PKA: 2.14±0.15(Predicted)
• CAS DataBase Reference: L-2,4-DICHLOROPHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: L-2,4-DICHLOROPHENYLALANINE(111119-36-9)
• EPA Substance Registry System: L-2,4-DICHLOROPHENYLALANINE(111119-36-9)

Safety Data

• Hazard Codes: Xi
• Hazardous Substances Data: 111119-36-9(Hazardous Substances Data)

Usage

General Description

L-2,4-Dichlorophenylalanine, also known as 2,4-Dichlorophenylalanine or 2,4-DCP, is a chemical compound that is a derivative of the amino acid phenylalanine. It is classified as a selective inhibitor of tyrosine hydroxylase, an enzyme involved in the synthesis of dopamine. L-2,4-Dichlorophenylalanine has been studied for its potential use in the treatment of various conditions related to dopamine dysfunction, such as Parkinson's disease, schizophrenia, and addiction. It is also used in research to study the role of dopamine in neurological and psychiatric disorders. Additionally, L-2,4-Dichlorophenylalanine has been investigated as a potential tool in the study of the central nervous system and as a building block for the synthesis of other chemical compounds.

InChI:InChI=1/C9H9Cl2NO2/c10-6-2-1-5(7(11)4-6)3-8(12)9(13)14/h1-2,4,8H,3,12H2,(H,13,14)/t8-/m1/s1

Upstream product

• 5472-68-4 rac-2,4-dichloro-Phe 
• 1201-99-6 trans-2,4-dichlorocinnamic acid 
• 874-42-0 2,4-dichlorobenzaldeyhde 
• 444726-81-2 2-acetamido-3-(2,4-dichlorophenyl)propionic acid 

Downstream Products

• 1357194-46-7 (S)-1-azido-3-(2,4-dichlorophenyl)propan-2-amine hydrochloride 
• 877057-26-6 (S)-tert-butyl-1-azido-3-(2,4-dichlorophenyl)propan-2-yl-carbamate 
• 877057-25-5 (S)-tert-butyl-1-(2,4-dichlorophenyl)-3-hydroxypropan-2-yl-carbamate 
• 1109216-86-5 C₉H₈Cl₂O₃ 

Relevant articles and documents

Telescopic one-pot condensation-hydroamination strategy for the synthesis of optically pure L-phenylalanines from benzaldehydes

A chemo-enzymatic telescopic approach was designed for the synthesis of L-arylalanines in high yield and optical purity, starting from commercially available and inexpensive substituted benzaldehydes. The method exploits a chemical Knoevenagel–Doebner condensation (optimised to give complete conversions in a short reaction time, employing microwave irradiation) and a biocatalytic phenylalanine ammonia lyase mediated hydroamination (for the stereoselective addition of ammonia). The two reactions can be run sequentially in one pot, bringing together the advantages of chemical and biological catalysis. The preparative applicability was demonstrated with the synthesis of five L-dihalophenylalanines (71–84% yield, 98–99% ee) of relevance as molecular probes, for medicinal chemistry and for the synthesis of pharmaceutical ingredients.

Use of whole cell culture of Aeromonas sp. as enantioselective scavenger: A facile preparation of l-amino acid derivatives in high enantiomeric excess

The bacterium Aeromonas sp. (CGMCC 2226) can enantioselectively scavenge d-isomer, making l-amino acid derivatives (AADs) in high ee. The enantioselective scavenger (ES) has shown a broad substrate scope. Eleven l-AADs, Phe derivatives substituted with methyl-, mono- and dichloro-, bromo-, and nitro-group, were produced in high ee from corresponding racemates.