2-Amino-3-(2-chlorophenyl)propanoic acid

Base Information

• Chemical Name: 2-Amino-3-(2-chlorophenyl)propanoic acid
• CAS No.: 14091-11-3
• Molecular Formula: C9H10ClNO2
• Molecular Weight: 199.637
• Hs Code.: 2922499990
• European Community (EC) Number: 237-939-2
• NSC Number: 154946,233876,28185
• Nikkaji Number: J2.230.810F
• Mol file: 14091-11-3.mol

Synonyms:14091-11-3;2-amino-3-(2-chlorophenyl)propanoic acid;2-Chloro-DL-Phenylalanine;o-Chloro-dl-phenylalanine;DL-Phenylalanine, 2-chloro-;O-Chlorophenylalanine;2-Amino-3-(2-chloro-phenyl)-propionic acid;2-Chloro-3-phenyl-DL-alanine;EINECS 237-939-2;MFCD00037774;NSC 233876;2-chlorophenylalanine;DL-PHE(2-CL)-OH;D-2-chlorophenylalanine;H-D-Phe(2-Cl)-OH.HCl;MFCD00077920;MFCD00077921;NSC28185;2-Amino-3-(2-chlorophenyl)propanoicacid;SCHEMBL43976;DL-beta-(o-Chlorophenyl)alanine;NSC-28185;NSC154946;NSC233876;AKOS000185911;AKOS016842352;AB01662;AB02989;AM82734;CS-W002170;DS-1249;FS-3217;HY-W002170;NSC-154946;NSC-233876;(S)-(-)-3,7-Dimethyl-6-octenoicacid;SY030197;SY035311;SY035312;2-Amino-3-(2-chlorophenyl)propionic acid;FT-0641748;FT-0642536;FT-0694497;EN300-140883;A885717;DL-2-AMINO-3-(2-CHLORO-PHENYL)-PROPIONIC ACID;F2147-6557;2-Amino-3-(2-chlorophenyl)propanoic acid (H-DL-Phe(2-Cl)-OH);1991-77-1;2-Chloro-DL-phenylalanine;2-Amino-3-(2-chlorophenyl)propanoic acid

Chemical Property of 2-Amino-3-(2-chlorophenyl)propanoic acid

Chemical Property:

• Appearance/Colour: White lens powder
• Melting Point: 216-219 °C
• Refractive Index: 1.593
• Boiling Point: 339.532 °C at 760 mmHg
• PKA: pK1: 2.23(+1);pK2: 8.94(0) (25°C)
• Flash Point: 159.143 °C
• PSA: 63.32000
• Density: 1.336 g/cm³
• LogP: 1.99470
• Storage Temp.: Store at 0-5°C
• Solubility.: Aqueous Acid (Slightly)
• XLogP3: -0.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 199.0400063
• Heavy Atom Count: 13
• Complexity: 187

Purity/Quality:

99% ^*data from raw suppliers

2-Chloro-DL-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC(C(=O)O)N)Cl
• Uses: 2-Chloro-DL-phenylalanine is used in the synthesis of 2-benzylpyrroles and 2-benzoylpyrroles with insecticidal and acaricidal activity.

Technology Process of 2-Amino-3-(2-chlorophenyl)propanoic acid

There total 16 articles about 2-Amino-3-(2-chlorophenyl)propanoic acid 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: 70.0%

2-(Benzhydrylidene-amino)-3-(2-chloro-phenyl)-propionic acid methyl ester (145243-37-4) → rac-2-chlorophenylalanine (14091-11-3,80126-50-7)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo00056a033

Reference yield:

(Z)-3-(2-chlorophenyl)-2-hydroxyacrylic acid → rac-2-chlorophenylalanine (14091-11-3,80126-50-7)

Guidance literature:

With 1,4-dihydronicotinamide adenine dinucleotide; potassium chloride; ammonium chloride; hydrogenchloride; Bacillus sphaericus wild type phenylalanine dehydrogenase; In various solvent(s); at 25 ℃; for 0.666667h; pH=8.0;

DOI:10.1039/b406364c

Reference yield:

1-chloro-2-(chloromethyl)benzene (611-19-8) → rac-2-chlorophenylalanine (14091-11-3,80126-50-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Mg / diethyl ether / 0.17 h / Heating

1.2: CdCl₂ / diethyl ether / 0.67 h / Heating

1.3: 32 percent / diethyl ether / 1 h / 0 °C

2.1: NH₄Cl; KCl; NADH / Bacillus sphaericus wild type phenylalanine dehydrogenase; aq. HCl / various solvent(s) / 0.67 h / 25 °C / pH 8.0

With 1,4-dihydronicotinamide adenine dinucleotide; potassium chloride; ammonium chloride; magnesium; hydrogenchloride; Bacillus sphaericus wild type phenylalanine dehydrogenase; In diethyl ether;

DOI:10.1039/b406364c

upstream raw materials:

N-benzoyl-2-chloro-phenylalanine

N-acetyl-3-(2-chlorophenyl)-2-ethoxycarbonyl alanine ethyl ester

2-(Benzhydrylidene-amino)-3-(2-chloro-phenyl)-propionic acid methyl ester

1-chloro-2-(chloromethyl)benzene

Downstream raw materials:

2-(2-chlorophenyl)ethanamine

(R)-2'-chlorophenylalanine

(2S)-2-amino-3-(2-chlorophenyl)propanoic acid

trans-2-chlorocinnamic acid

Refernces

• 1、 Weise, Nicholas J.,Thapa, Prasansa,Ahmed, Syed T.,Heath, Rachel S.,Parmeggiani, Fabio,Turner, Nicholas J.,Flitsch, Sabine L.. "Bi-enzymatic Conversion of Cinnamic Acids to 2-Arylethylamines". . p. 995 - 998. Retrieved 2020/01/21.
• 2、 Lovelock, Sarah L.,Lloyd, Richard C.,Turner, Nicholas J.. "Phenylalanine ammonia lyase catalyzed synthesis of amino acids by an MIO-cofactor independent pathway". supporting information. p. 4652 - 4656. Retrieved 2014/05/20.