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

Base Information

• Chemical Name: (S)-2-amino-3-(2-nitrophenyl)propanoic acid
• CAS No.: 19883-75-1
• Molecular Formula: C₉H₁₀N₂O₄
• Molecular Weight: 210.189
• Hs Code.: 2922499990
• European Community (EC) Number: 815-417-0
• DSSTox Substance ID: DTXSID401347413
• Nikkaji Number: J829.106C
• Wikidata: Q76148960
• Mol file: 19883-75-1.mol

Synonyms:2-nitrophenylalanine

Chemical Property of (S)-2-amino-3-(2-nitrophenyl)propanoic acid

Chemical Property:

• Vapor Pressure: 1.25E-06mmHg at 25°C
• Melting Point: 223 °C (dec.)
• Refractive Index: 1.614
• Boiling Point: 385.4 °C at 760 mmHg
• PKA: 2.03±0.10(Predicted)
• Flash Point: 186.9 °C
• PSA: 109.14000
• Density: 1.408 g/cm³
• LogP: 1.77270
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly, Heated, Sonicated), Methanol (Slightly)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 210.06405680
• Heavy Atom Count: 15
• Complexity: 251

Purity/Quality:

97% ^*data from raw suppliers

2-Nitro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)CC(C(=O)O)N)[N+](=O)[O-]
• Isomeric SMILES: C1=CC=C(C(=C1)C[C@@H](C(=O)O)N)[N+](=O)[O-]
• Uses: L-2-Nitrophenylalanine is a derivative of L-phenylalanine (P319415), and is used in the photocleavage of polypeptide backbones. L-Phenylalanine is an essential amino acid. L-Phenylalanine is biologically converted into L-tyrosine, another one of the DNA-encoded amino acids, which in turn is converted to L-DOPA and further converted into dopamine, norepinephrine, and epinephrine.

Technology Process of (S)-2-amino-3-(2-nitrophenyl)propanoic acid

There total 14 articles about (S)-2-amino-3-(2-nitrophenyl)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: 58.0%

2-nitrocinnamic acid (612-41-9) → (2S)-2-amino-3-(2-nitrophenyl)propanoic acid (1991-82-8,35378-63-3,19883-75-1)

Guidance literature:

With ammonium hydroxide; borane-ammonia complex; In aq. buffer; at 37 ℃; pH=9.6; Enzymatic reaction;

DOI:10.1002/anie.201410670

Reference yield: 24.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → 4-nitrophenylalanine (1991-83-9,2922-40-9,56613-61-7,949-99-5) + DL-2-nitrophenylalanine (1991-82-8,19883-75-1,35378-63-3)

Guidance literature:

With sulfuric acid; nitric acid; at -10 ℃; for 3.5h;

DOI:10.1021/jm00117a015

Reference yield:

3-amino-3-(2-nitrophenyl)propionic acid (5678-48-8,732242-02-3,756814-14-9) → (2S)-2-amino-3-(2-nitrophenyl)propanoic acid (1991-82-8,35378-63-3,19883-75-1) + C9H10N2O4 (732242-02-3,756814-14-9) + 2-nitrocinnamic acid (612-41-9)

Guidance literature:

With phenylalanine 2,3-aminomutase from Pantoea agglomerans; ammonium carbonate; at 20 ℃; for 20h; pH=8; enantioselective reaction; Enzymatic reaction;

DOI:10.1039/c6ra02964g

upstream raw materials:

L-phenylalanine

2-nitrocinnamic acid

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

2-nitrocinnamic acid

Downstream raw materials:

(2R)-2-amino-3-(2-nitrophenyl)propanoic acid

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

2-nitrocinnamic acid

(3S)-3-amino-1-hydroxy-3,4-dihydroquinolin-2(1H)-one hydrochloride