Boc-3-Nitro-L-Phenylalanine

Base Information

• Chemical Name: Boc-3-Nitro-L-Phenylalanine
• CAS No.: 131980-29-5
• Molecular Formula: C14H18N2O6
• Molecular Weight: 310.307
• Hs Code.: 29242990
• DSSTox Substance ID: DTXSID60927486
• Wikidata: Q72450169
• Mol file: 131980-29-5.mol

Synonyms:Boc-3-Nitro-L-Phenylalanine;131980-29-5;Boc-L-3-Nitrophenylalanine;Boc-Phe(3-NO2)-OH;(S)-2-((tert-butoxycarbonyl)amino)-3-(3-nitrophenyl)propanoic acid;(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-(3-nitrophenyl)propanoic acid;(S)-2-[(tert-butoxycarbonyl)amino]-3-(3-nitrophenyl)propanoic acid;MFCD01317033;SCHEMBL2727571;DTXSID60927486;OWTGPXDXLMNQKK-NSHDSACASA-N;AKOS015836512;AKOS015890673;AC-2129;AM83448;CS-W016706;AS-31083;Boc-Phe(3-NO2)-OH, >=98.0% (HPLC);EN300-7383715;J-006099;Boc-L-3-nitrophenylalanine (Boc-L-Phe(3-NO2)-OH);N-[tert-Butoxy(hydroxy)methylidene]-3-nitrophenylalanine;(S)-2-tert-butoxycarbonylamino-3-(3-nitrophenyl)propionic acid;(S)-2-(tert-butoxycarbonylamino)-3-(3-nitrophenyl)propanoic acid;(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-(3-nitrophenyl)propanoic acid

Chemical Property of Boc-3-Nitro-L-Phenylalanine

Chemical Property:

• Vapor Pressure: 4.27E-11mmHg at 25°C
• Refractive Index: 1.553
• Boiling Point: 506.9 °C at 760 mmHg
• PKA: 3.73±0.10(Predicted)
• Flash Point: 260.3 °C
• PSA: 121.45000
• Density: 1.29 g/cm³
• LogP: 3.02930
• Storage Temp.: Store at R.T.
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 310.11648630
• Heavy Atom Count: 22
• Complexity: 426

Purity/Quality:

99% ^*data from raw suppliers

Boc-3-nitro-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC(=CC=C1)[N+](=O)[O-])C(=O)O
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC(=CC=C1)[N+](=O)[O-])C(=O)O
• Uses: Boc-L-3-Nitrophenylalanine is a protected 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 Boc-3-Nitro-L-Phenylalanine

There total 9 articles about Boc-3-Nitro-L-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: 85.0%

di-tert-butyl dicarbonate (24424-99-5) + L-3'-nitrophenylalanine hydrochloride → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-nitrophenyl)propanoic acid (131980-29-5)

Guidance literature:

With sodium hydroxide; In water; tert-butyl alcohol; for 3h; Ambient temperature;

DOI:10.1021/jm00014a017

Reference yield: 53.0%

1-bromomethyl-3-nitrobenzene (3958-57-4) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-nitrophenyl)propanoic acid (131980-29-5)

Guidance literature:

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + (2S)-2-amino-3-(3-nitrophenyl)propanoic acid (19883-74-0) → (2S)-2-[(tert-butoxycarbonyl)amino]-3-(3-nitrophenyl)propanoic acid (131980-29-5)

Guidance literature:

di-tert-butyl dicarbonate; (2S)-2-amino-3-(3-nitrophenyl)propanoic acid; With sodium hydroxide; In 1,4-dioxane; water; at 23 ℃; for 1.5h;

With potassium hydrogensulfate; In 1,4-dioxane; water; pH=5;

upstream raw materials:

di-tert-butyl dicarbonate

DL-N-acetyl-3-nitrophenylalanine

ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate

diethyl 2-(acetylamino)-2-(3-nitrobenzyl)malonate

Downstream raw materials:

C₁₆H₂₃N₃O₅

Refernces

• 1、 -. "N-acylamino acid amide compounds and intermediates for preparation thereof". . . Retrieved 2008/06/13.