4-Chloro-DL-phenylalanine methyl ester hydrochloride

Base Information

• Chemical Name: 4-Chloro-DL-phenylalanine methyl ester hydrochloride
• CAS No.: 14173-40-1
• Molecular Formula: C₁₀H₁₂ClNO₂*ClH
• Molecular Weight: 250.125
• Hs Code.: 29224999
• European Community (EC) Number: 238-024-0
• UNII: OC0YKX1H41
• DSSTox Substance ID: DTXSID60931184
• Wikidata: Q27285563
• ChEMBL ID: CHEMBL1256173
• Mol file: 14173-40-1.mol

Synonyms:14173-40-1;4-Chloro-DL-phenylalanine methyl ester hydrochloride;methyl 2-amino-3-(4-chlorophenyl)propanoate hydrochloride;H-DL-Phe(4-Cl)-OMe.HCl;4-Chloro-DL-phenylalanine methyl ester, HCl;DL-p-Chlorophenylalanine methyl ester hydrochloride;PCPA methyl ester (hydrochloride);H-p-Chloro-DL-Phe-OMe HCl;pCPA methyl ester hydrochloride;Phenylalanine, 4-chloro-, methyl ester, hydrochloride (1:1);4-Chlorophenylalanine Methyl Ester Hydrochloride;UNII-OC0YKX1H41;OC0YKX1H41;DL-4-Chlorophenylalanine methyl ester hydrochloride;ALANINE, 3-(p-CHLOROPHENYL)-, METHYL ESTER, HYDROCHLORIDE, DL-;H-p-Chloro-D-Phe-OMe HCl;4,4-DIACETOXYSTIBENE;p-Chlorophenylalanine methyl ester hydrochloride;(R)-2-Amino-3-(4-chloro-phenyl)-propionic acid methyl ester . HCl;H-4-Chloro-D-Phe-OMe . HCl;(RS)-2-Amino-3-(4-chloro-phenyl)-propionic acid methyl ester . HCl;H-4-Chloro-DL-Phe-OMe . HCl;4-Chloro-L-phenylalanine methyl ester HCl;MFCD00012530;4-Chloro-D-phenylalaninemethylesterhydrochloride;EU-0100311;C10H12ClNO2.ClH;4-Chloro-DL-Phe-OMe.HCl;MLS002153254;H-D-Phe(4-Cl)-OMe.HCl;SCHEMBL1168261;CHEMBL1256173;DTXSID60931184;Tox21_500311;AKOS016002251;CCG-221615;LP00311;NCGC00093758-01;NCGC00260996-01;AM803206;DL-p-Chlorophenylalanine methyl ester HCl;SMR001230706;4-Chloro-DL-phenylalanine methyl ester HCl;HY-101456;CS-0021369;FT-0637025;FT-0651264;C 3635;M03172;EN300-7387742;A807800;A822024;SR-01000075756;SR-01000075756-1;Q27285563;methyl 2-azanyl-3-(4-chlorophenyl)propanoate hydrochloride;DL-Methyl 2-amino-3-(4-chlorophenyl)propanoate hydrochloride;2-amino-3-(4-chlorophenyl)propanoic acid methyl ester hydrochloride;METHYL 2-AMINO-3-(4-CHLOROPHENYL)PROPANOATE HYDROCHLORIDE, (2RS)-;(RS)-2-Amino-3-(4-chloro-phenyl)-propionic acid methyl ester HCl;H-4-Chloro-DL-Phe-OMe HCl

Chemical Property of 4-Chloro-DL-phenylalanine methyl ester hydrochloride

Chemical Property:

• Appearance/Colour: white to off-white powder
• Melting Point: 186-189 °C(lit.)
• Boiling Point: 296.3 °C at 760 mmHg
• Flash Point: 133 °C
• PSA: 52.32000
• LogP: 2.88510
• Storage Temp.: −20°C
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 249.0323340
• Heavy Atom Count: 15
• Complexity: 191

Purity/Quality:

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

4-Chloro-DL-phenylalanine methyl ester hydrochloride ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=C(C=C1)Cl)N.Cl
• Uses: 4-Chloro-DL-phenylalanine methyl ester hydrochloride has been used to induce 5-hydroxytryptamine (5-HT) depletion in rats.

Technology Process of 4-Chloro-DL-phenylalanine methyl ester hydrochloride

There total 17 articles about 4-Chloro-DL-phenylalanine methyl ester hydrochloride 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: 100.0%

methanol (67-56-1) + DL-Phe(4Cl) (7424-00-2,1991-78-2) → 2-amino-3-(4-chlorophenyl)propionic acid methyl ester hydrochloride (14173-40-1,23434-91-5,33965-47-8,60594-65-2)

Guidance literature:

With thionyl chloride; for 4h; Heating;

DOI:10.1021/ja8018687

Reference yield: 66.0%

methanol (67-56-1) + p-chlorophenylalanine (14173-39-8,1991-78-2) → (S)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride (14173-40-1,23434-91-5,33965-47-8,60594-65-2)

Guidance literature:

With hydrogenchloride; at 0 ℃;

DOI:10.1002/ardp.201100109

Reference yield:

(2S)-2-azido-3-(4-chlorophenyl)propionic acid methyl ester (182249-59-8) → (S)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride (14173-40-1,23434-91-5,33965-47-8,60594-65-2)

Guidance literature:

With hydrogenchloride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; for 4h; under 760 Torr; Ambient temperature;

DOI:10.1021/jo960956l

upstream raw materials:

DL-Phe(4Cl)

methanol

2-acetylamino-2-(4-chlorobenzyl)malonic acid diethyl ester

2-amino-3-(4-chlorophenyl)propionic acid hydrochloride

Downstream raw materials:

ethyl 3-(4-chlorophenyl)-2-pyrrolidin-N-yl-propanoate

N-(Toluene-4-sulfonyl)-L-prolyl-L-(4-chloro)phenylalanine methyl ester

2-[[[(ethoxycarbonyl)amino]thioxomethyl]amino]-3-(4-chlorophenyl)-propionic acid methyl ester

C₁₃H₁₂ClNO₃

Refernces

• 1、 Muszak, Damian,?abuzek, Beata,Brela, Mateusz Z.,Twarda-Clapa, Aleksandra,Czub, Miroslawa,Musielak, Bogdan,Surmiak, Ewa,Holak, Tad A.. "The synthesis and characterization of tetramic acid derivatives as Mdm2-p53 inhibitors". . p. 161 - 174. Retrieved 2019/04/26.
• 2、 Da Silva, Marcos Reinaldo,De Mattos, Marcos Carlos,De Oliveira, Maria Da Concei??o Ferreira,De Lemos, Telma Leda Gomes,Ricardo, Nágila Maria Pontes Silva,De Gonzalo, Gonzalo,Lavandera, Iván,Gotor-Fernández, Vicente,Gotor, Vicente. "Asymmetric chemoenzymatic synthesis of N-acetyl-α-amino esters based on lipase-catalyzed kinetic resolutions through interesterification reactions". . p. 2264 - 2271. Retrieved 2014/03/21.