(2S)-2-ammonio-3-(4-chlorophenyl)propanoate

Base Information

• Chemical Name: (2S)-2-ammonio-3-(4-chlorophenyl)propanoate
• CAS No.: 14173-39-8
• Molecular Formula: C9H10ClNO2
• Molecular Weight: 199.637
• Hs Code.: 29224999
• Mol file: 14173-39-8.mol

Synonyms:(2S)-2-ammonio-3-(4-chlorophenyl)propanoate;A838070

Chemical Property of (2S)-2-ammonio-3-(4-chlorophenyl)propanoate

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 3.54E-05mmHg at 25°C
• Melting Point: 263 °C
• Refractive Index: 1.589
• Boiling Point: 339.5 °C at 760 mmHg
• PKA: 2.18±0.10(Predicted)
• Flash Point: 159.1 °C
• PSA: 63.32000
• Density: 1.336 g/cm³
• LogP: 1.99470
• Storage Temp.: Store at RT.
• Solubility.: Aqueous Base (Slightly), Water (Slightly)
• Water Solubility.: Soluble in acetic acid. Slightly soluble in water.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 199.0400063
• Heavy Atom Count: 13
• Complexity: 173

Purity/Quality:

98%, ^*data from raw suppliers

4-Chloro-L-phenylalanine 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,T
• Hazard Codes: T,Xi
• Statements: 25-43
• Safety Statements: 36/37-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)[O-])[NH3+])Cl
• Isomeric SMILES: C1=CC(=CC=C1C[C@@H](C(=O)[O-])[NH3+])Cl
• Uses: 4-Chloro-L-phenylalanine is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals.

Technology Process of (2S)-2-ammonio-3-(4-chlorophenyl)propanoate

There total 32 articles about (2S)-2-ammonio-3-(4-chlorophenyl)propanoate 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: 83.0%

(±)-ethyl 2-amino-3-(4-chlorophenyl)propanoate (29622-19-3,38964-54-4) → p-chlorophenylalanine (14173-39-8,1991-78-2) + D-4-chlorophenylalanine ethyl ester (166449-97-4,38964-54-4)

Guidance literature:

With lithium hydroxide; at 37 ℃; for 24h; α-chymotrypsin;

DOI:10.1016/0223-5234(90)90162-V

Reference yield: 73.2%

N-acetyl-4-chlorophenylalanine (14091-10-2) → p-chlorophenylalanine (14173-39-8,1991-78-2)

Guidance literature:

With hydrogenchloride; In water; at 95 - 100 ℃; for 6h;

DOI:10.1080/00397911.2012.748075

Reference yield: 59.0%

3-(4-chlorophenyl)prop-2-enoic acid (1615-02-7,940-62-5) → p-chlorophenylalanine (14173-39-8,1991-78-2)

Guidance literature:

With ammonium hydroxide; Petroselinum crispum phenylalanine ammonialyase (1U); at 37 ℃; for 24h; pH=10;

DOI:10.1002/1521-3765(20000915)6:18<3386::AID-CHEM3386>3.0.CO;2-5

upstream raw materials:

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

(±)-ethyl 2-amino-3-(4-chlorophenyl)propanoate

(2S,5S)-2-tert-Butyl-5-(4-chloro-benzyl)-3-methyl-4-oxo-imidazolidine-1-carboxylic acid tert-butyl ester

4-amino-L-phenylalanine

Downstream raw materials:

Boc-p-chloro-L-Phe-OH

p-Chlor-m-nitrophenylalanin

(S)-2-amino-3-(4-chloro-phenyl)-propionic acid methyl ester hydrochloride

(S)-2-Acetylsulfanyl-3-(4-chloro-phenyl)-propionic acid

Refernces

• 1、 Danalev, Dancho,Borisova, Desislava,Yaneva, Spaska,Georgieva, Maya,Balacheva, Anelia,Dzimbova, Tatyana,Iliev, Ivan,Pajpanova, Tamara,Zaharieva, Zdravka,Givechev, Ivan,Naydenova, Emilia. "Synthesis, in vitro biological activity, hydrolytic stability and docking of new analogs of BIM-23052 containing halogenated amino acids". . p. 1581 - 1592. Retrieved 2020/11/23.
• 2、 Weise, Nicholas J.,Ahmed, Syed T.,Parmeggiani, Fabio,Turner, Nicholas J.. "Kinetic Resolution of Aromatic β-Amino Acids Using a Combination of Phenylalanine Ammonia Lyase and Aminomutase Biocatalysts". . p. 1570 - 1576. Retrieved 2017/05/05.