(R)-2-Amino-3-(o-tolyl)propanoic acid

Base Information

• Chemical Name: (R)-2-Amino-3-(o-tolyl)propanoic acid
• CAS No.: 80126-54-1
• Molecular Formula: C₁₀H₁₃NO₂
• Molecular Weight: 179.219
• Hs Code.: 2922499990
• DSSTox Substance ID: DTXSID301313334
• Nikkaji Number: J524.385H
• Mol file: 80126-54-1.mol

Synonyms:80126-54-1;(R)-2-Amino-3-(o-tolyl)propanoic acid;2-Methyl-D-phenylalanine;D-2-Methylphenylalanine;(2R)-2-amino-3-(2-methylphenyl)propanoic acid;D-Phenylalanine, 2-methyl-;O-METHYL-D-PHENYLALANINE;(2R)-2-azaniumyl-3-(2-methylphenyl)propanoate;D-2-METHYLPHE;H-D-PHE(2-ME)-OH;2-Methy-D-Phenylalanine;D-2-Methyl Phenylalanine;H-O-ME-D-PHE-OH;SCHEMBL383453;DTXSID301313334;MFCD01860870;AKOS016843584;AC-5867;AM83410;PS-12170;CS-0152968;(R)-2-AMINO-3-O-TOLYLPROPANOIC ACID;D-2-Methylphenylalanine (H-D-Phe(2-Me)-OH);EN300-1298518;A839847

Chemical Property of (R)-2-Amino-3-(o-tolyl)propanoic acid

Chemical Property:

• Melting Point: 259-260 °C (decomp)
• Refractive Index: 1.561
• Boiling Point: 326.2 °C at 760 mmHg
• PKA: 2.25±0.10(Predicted)
• Flash Point: 151.1 °C
• PSA: 49.33000
• Density: 1.165 g/cm³
• LogP: 1.95300
• Storage Temp.: Store at -15°C
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 179.094628657
• Heavy Atom Count: 13
• Complexity: 182

Purity/Quality:

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

2-Methyl-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC=CC=C1CC(C(=O)O)N
• Isomeric SMILES: CC1=CC=CC=C1C[C@H](C(=O)O)N

Technology Process of (R)-2-Amino-3-(o-tolyl)propanoic acid

There total 26 articles about (R)-2-Amino-3-(o-tolyl)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: 90.0%

2-(Benzhydrylidene-amino)-3-o-tolyl-propionic acid methyl ester (145243-36-3) → 2-(fluoromethyl)-D-phenylalanine (1991-86-2,80126-54-1)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo00056a033

Reference yield: 83.0%

2'-methyl-(2S)-α-phenylalanine (80126-53-0,1991-86-2,80126-54-1) → 2-(fluoromethyl)-D-phenylalanine (1991-86-2,80126-54-1)

Guidance literature:

With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride; In aq. buffer; at 20 ℃; for 24h; pH=9; enantioselective reaction; Microbiological reaction;

DOI:10.1002/adsc.201600682

Reference yield: 76.0%

2-(Benzhydrylidene-amino)-3-o-tolyl-propionic acid methyl ester (145243-36-3) → 2-amino-3-(2-methylphenyl)propanoic acid (22888-51-3,1991-86-2,80126-54-1)

Guidance literature:

With hydrogenchloride;

DOI:10.1021/jo00056a033

upstream raw materials:

2-acetylamino-2-(2-methylbenzyl)malonic acid diethyl ester

1-chloromethyl-2-methylbenzene

ethyl 2-acetamido-2-cyanoacetate

2-(Benzhydrylidene-amino)-3-o-tolyl-propionic acid methyl ester

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、 Zhu, Longbao,Feng, Guoqiang,Ge, Fei,Song, Ping,Wang, Taotao,Liu, Yi,Tao, Yugui,Zhou, Zhemin. "One-Pot Enzymatic Synthesis of d-Arylalanines Using Phenylalanine Ammonia Lyase and l-Amino Acid Deaminase". . p. 1 - 15. Retrieved 2018/06/11.