2,4-Dichloro-L-phenylalanine

Base Information

• Chemical Name: 2,4-Dichloro-L-phenylalanine
• CAS No.: 111119-36-9
• Molecular Formula: C9H9Cl2NO2
• Molecular Weight: 234.082
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID60375802
• Nikkaji Number: J2.638.860K
• Mol file: 111119-36-9.mol

Synonyms:111119-36-9;2,4-Dichloro-L-phenylalanine;L-2,4-Dichlorophenylalanine;H-PHE(2,4-DICL)-OH;(2S)-2-amino-3-(2,4-dichlorophenyl)propanoic acid;(S)-2-Amino-3-(2,4-dichlorophenyl)propanoic acid;L-Phenylalanine, 2,4-dichloro-;(2S)-2-azaniumyl-3-(2,4-dichlorophenyl)propanoate;MFCD01860882;SCHEMBL44905;DTXSID60375802;GWHQTNKPTXDNRM-QMMMGPOBSA-N;2,4-DICHLORO-PHENYLALANINE;AKOS016843996;AC-5846;AM82013;CS-W014167;HY-W013451;AS-48689;EN300-199891;F52527;(S)-alpha-Amino-2,4-dichlorobenzenepropanoic acid;A802295;L-2,4-Dichlorophenylalanine (H-L-Phe(2,4-diCl)-OH);(S)-2-AMINO-3-(2,4-DICHLORO-PHENYL)-PROPIONIC ACID

Chemical Property of 2,4-Dichloro-L-phenylalanine

Chemical Property:

• Vapor Pressure: 4.55E-06mmHg at 25°C
• Melting Point: 238-240 °C
• Refractive Index: 1.601
• Boiling Point: 368.1 °C at 760 mmHg
• PKA: 2.14±0.15(Predicted)
• Flash Point: 176.4 °C
• PSA: 63.32000
• Density: 1.45 g/cm³
• LogP: 2.64810
• Storage Temp.: Store at 0-5°C
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 233.0010339
• Heavy Atom Count: 14
• Complexity: 213

Purity/Quality:

98%,99%, ^*data from raw suppliers

L-2,4-Dichlorophenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=C(C=C1Cl)Cl)CC(C(=O)O)N
• Isomeric SMILES: C1=CC(=C(C=C1Cl)Cl)C[C@@H](C(=O)O)N

Technology Process of 2,4-Dichloro-L-phenylalanine

There total 4 articles about 2,4-Dichloro-L-phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 46.0%

rac-2,4-dichloro-Phe (5472-68-4) → (S)-2-amino-3-(2,4-dichlorophenyl)propanoic acid (111119-36-9)

Guidance literature:

With sodium hydroxide; oxygen; at 30 ℃; for 22h; pH=7.3; optical yield given as %ee; enantioselective reaction; aq. buffer; Enzymatic reaction;

DOI:10.1016/j.bmcl.2008.12.100

Reference yield:

trans-2,4-dichlorocinnamic acid (1201-99-6,20595-45-3,20595-46-4) → (S)-2-amino-3-(2,4-dichlorophenyl)propanoic acid (111119-36-9)

Guidance literature:

With ammonium hydroxide; carbon dioxide; In dimethyl sulfoxide; at 37 ℃; for 12h; pH=10; Reagent/catalyst; stereoselective reaction; Enzymatic reaction;

DOI:10.1016/j.tet.2015.12.063

Reference yield:

2-acetamido-3-(2,4-dichlorophenyl)propionic acid (444726-81-2) → 2,4-dichloro-D-phenylalanine (114872-98-9) + (S)-2-amino-3-(2,4-dichlorophenyl)propanoic acid (111119-36-9)

Guidance literature:

With hydrogenchloride; In water; at 95 - 100 ℃; for 6h; Overall yield = 62 %;

DOI:10.1080/00397911.2012.748075

upstream raw materials:

rac-2,4-dichloro-Phe

2-acetamido-3-(2,4-dichlorophenyl)propionic acid

2,4-dichlorobenzaldeyhde

trans-2,4-dichlorocinnamic acid

Downstream raw materials:

(S)-1-azido-3-(2,4-dichlorophenyl)propan-2-amine hydrochloride

(S)-tert-butyl-1-azido-3-(2,4-dichlorophenyl)propan-2-yl-carbamate

(S)-tert-butyl-1-(2,4-dichlorophenyl)-3-hydroxypropan-2-yl-carbamate

C₉H₈Cl₂O₃

Refernces

• 1、 Arava, Veera Reddy,Amasa, Srinivasulu Reddy,Goud Bhatthula, Bharat Kumar,Kompella, Laxmi Srinivas,Matta, Venkata Prasad,Subha. "Asymmetric synthesis of unnatural amino acids and tamsulosin chiral intermediate". supporting information. p. 2892 - 2897. Retrieved 2013/09/02.