4-Nitro-DL-phenylalanine

Base Information

• Chemical Name: 4-Nitro-DL-phenylalanine
• CAS No.: 2922-40-9
• Molecular Formula: C₉H₁₀N₂O₄
• Molecular Weight: 210.189
• Hs Code.: 29224999
• European Community (EC) Number: 220-868-6
• NSC Number: 152925,148865,14786
• DSSTox Substance ID: DTXSID40862482
• Nikkaji Number: J2.012.431H
• Wikidata: Q27121246
• Metabolomics Workbench ID: 57024
• Mol file: 2922-40-9.mol

Synonyms:4-nitrophenylalanine;4-nitrophenylalanine, (DL)-isomer;4-nitrophenylalanine, (L)-isomer;p-nitrophenylalanine

Chemical Property of 4-Nitro-DL-phenylalanine

Chemical Property:

• Appearance/Colour: beige powder
• Vapor Pressure: 1.34E-07mmHg at 25°C
• Melting Point: 236-237 °C (dec.)(lit.)
• Refractive Index: 1.614
• Boiling Point: 414.1 °C at 760 mmHg
• PKA: 2.12±0.10(Predicted)
• Flash Point: 204.2 °C
• PSA: 109.14000
• Density: 1.408 g/cm³
• LogP: 1.77270
• Storage Temp.: Store at RT.
• XLogP3: -1.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 210.06405680
• Heavy Atom Count: 15
• Complexity: 243

Purity/Quality:

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

4-Nitro-DL-phenylalanine hydrate 99+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T, C, F
• Hazard Codes: T,C,F
• Statements: 25-34-11
• Safety Statements: 45-36/37/39-26-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CC(C(=O)O)N)[N+](=O)[O-]
• Uses: 4-Nitro-DL-phenylalanine is a chromophore used as a convenient UV tag for determination of overall purity of b-turn mimetics. 4-Nitro-DL-phenylalanine may be used as an internal standard for the determination of β-N-methylamino-L-alanine (L-BMAA) in environmental aqueous samples using proton nuclear magnetic resonance (1H NMR) technique.

Technology Process of 4-Nitro-DL-phenylalanine

There total 29 articles about 4-Nitro-DL-phenylalanine 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-acetylamino-2-(4-nitrobenzyl)malonic acid diethyl ester (6265-87-8) → 4-nitrophenylalanine (1991-83-9,2922-40-9,56613-61-7,949-99-5)

Guidance literature:

With hydrogenchloride; acetic acid; In water; for 24h; Heating;

DOI:10.1021/jm070401q

Reference yield: 50.0%

H2 S(g) + 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)

Guidance literature:

With nitric acid; In concentrated H₂ SO₄;

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

upstream raw materials:

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

formylamino-(4-nitro-benzyl)-malonic acid diethyl ester

Phenylalanine

(4-nitro-benzyl)-malonic acid

Downstream raw materials:

4-<(4-nitrophenyl)methyl>imidazolidine-2,5-dione

4-nitro-benzoic acid

methyl 3-(4-aminophenyl)-2-((tert-butoxycarbonyl)amino)propanoate

2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-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、 Parmeggiani, Fabio,Lovelock, Sarah L.,Weise, Nicholas J.,Ahmed, Syed T.,Turner, Nicholas J.. "Synthesis of D- and L-Phenylalanine Derivatives by Phenylalanine Ammonia Lyases: A Multienzymatic Cascade Process". . p. 4608 - 4611. Retrieved 2015/04/14.