33305-77-0

Basic information

• Product Name: BOC-L-4-Nitrophe
• Synonyms: BOC-PNO2-L-PHE-OH;BOC-(P-NO2)PHE-OH;BOC-P-NITRO-PHENYLALANINE;BOC-P-NITRO-PHE-OH;BOC-PHE(P-NO2)-OH;BOC-PHE(4-NO2)-OH;BOC-L-4-NITROPHE;BOC-L-4-NITROPHENYLALANINE
• CAS NO: 33305-77-0
• Molecular Formula: C₁₄H₁₈N₂O₆
• Molecular Weight: 310.3
• EINECS: 251-450-1
• Product Categories: Amino Acids;Phenylalanine [Phe, F];Unusual Amino Acids;Boc-Amino acid series
• Mol File: 33305-77-0.mol
• Article Data: 24

Chemical Properties

• Melting Point: 107°C
• Boiling Point: 509.3oC at 760 mmHg
• Flash Point: 261.8oC
• Appearance: /
• Density: 1.29 g/cm3
• Vapor Pressure: 3.4E-11mmHg at 25°C
• Refractive Index: 1.553
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethanol (Slightly)
• PKA: 3.70±0.10(Predicted)
• BRN: 2820671
• CAS DataBase Reference: BOC-L-4-Nitrophe(CAS DataBase Reference)
• NIST Chemistry Reference: BOC-L-4-Nitrophe(33305-77-0)
• EPA Substance Registry System: BOC-L-4-Nitrophe(33305-77-0)

Safety Data

• Hazard Codes: Xi
• Safety Statements: 24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 33305-77-0(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow powder

Uses

N-Boc-p-nitro-L-phenylalanine is the N-Boc protected form of p-Nitro-L-phenylalanine (N502725, Hydrate) and is a useful synthetic intermediate in the synthesis of Hydroxymelphalan (H939850); an analog of Melphalan (M216900) which is an antineoplastic.

InChI:InChI=1/C14H18N2O6/c1-14(2,3)22-13(19)15-11(12(17)18)8-9-4-6-10(7-5-9)16(20)21/h4-7,11H,8H2,1-3H3,(H,15,19)(H,17,18)/t11-/m1/s1

Upstream product

• 1070-19-5 N-(tert-butyloxycarbonyl) azide 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 63-91-2 L-phenylalanine 
• 1991-83-9 4-nitrophenylalanine 
• 7732-18-5 water 
• 74651-77-7 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 673-06-3 D-(R)-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 56613-61-7 (R)-4-nitro-phenylalanine 
• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 74-96-4 ethyl bromide 
• 65615-89-6 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propanoate 
• 80994-44-1 {[(tert-butoxycarbonyl)oxy]amino}(phenyl)acetonitrile 

Downstream Products

• 116366-27-9 (S)-N-[(tert-butyloxy)carbonyl]-[4-nitrophenyl]alanine tert-butyl ester 
• 76378-70-6 (S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester 
• 73385-89-4 N-(tert-butyloxycarbonyl)-L-4-nitrophenylalanyl-L-prolinamide 
• 87363-45-9 C₂₈H₃₄N₄O₁₁ 
• 142995-33-3 Boc-Phe(4-NO₂)-NMeBzl 
• 174833-45-5 N-tert-butyloxycarbonyl-p-nitro-L-phenylalanine 2-(trimethylsilyl)ethyl ester 
• 199336-07-7 {(1S,2S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-cyclohexyl}-carbamic acid benzyl ester 
• 122566-51-2 N^α-t-BOC-trans-4-aminocyclohexyl-D-alanine 
• 132695-92-2 N^α-t-BOC-cis-4-aminocyclohexyl-D-alanine 
• 526223-50-7 (S)-2-{(2S,3S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-nitro-phenyl)-propionylamino]-3-hydroxy-butyrylamino}-3-phenyl-propionic acid methyl ester 
• 174698-99-8 [(S)-1-[(1S,2S)-2-Hydroxy-1-((R)-1-phenyl-ethylcarbamoyl)-propylcarbamoyl]-2-(4-nitro-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 65615-89-6 methyl (S)-2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propanoate 
• 55533-24-9 (2R)-3-(4-aminophenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid 
• 340732-99-2 methyl 2-[(2S)-1-[(2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-nitrophenyl)propanoyl]-4-[2-(tert-butoxy)-2-oxoethyl]-3-oxopiperazinyl]acetate 

Relevant articles and documents

Synthesis of N-[(tert-Butoxy)carbonyl]-3-(9,10-dihydro-9-oxoacridin-2-yl)-L-alanine, a New Fluorescent Amino Acid Derivative

A simple synthesis of a new, highly fluorescent amino acid and of its protected derivative useful in peptide studies is described. The obtained derivative, N-[(tert-butoxy)carbonyl]-3-(9,10-dihydro-9-oxoacridin-2-yl)-L-alanine (6), shows intense long-wave absorption (above 360 nm) and emission (above 400 nm). The quantum yield of fluorescence of the investigated compound is very high, so it can serve as a sensitive analytical probe useful, e.g., in analysis of peptide conformations.

NITRATION

The present invention relates to a process for preparing a nitrated compound, comprising the step of reacting a compound (A) comprising at least one substituted or unsubstituted aromatic or heteroaromatic ring, wherein said heteroaromatic ring comprises at least one heteroatom selected from the group consisting of oxygen, sulfur, phosphor, selenium and nitrogen, with a compound of formula (I) wherein Y is selected from the group consisting of hydrogen and nitro.

Synthesis, characterization, and biological study of phenylalanine amide derivatives

In the present study, a series of amide derivatives of 4-nitro-l-phenylalanine were synthesized with good yield from 4-nitro-l-phenylalanine and substituted anilines using propylphosphonic anhydride (T3P) as coupling reagent and were characterized through the IR, LC–MS, 1H and 13C NMR spectral studies. The isolated products were screened for antimicrobial and antioxidant activities. Some of the compounds showed Microsporum gypsuem activity or were active against Candida albicans, also a few of compounds showed antibacterial activities. The resultant compounds screened for anti-oxidant activity, which showed good activity for DPPH scavenging and ABTS assay methods and others had moderately activity. Some amide compounds act as metal chelating ligands with Fe2+ ions. Graphical abstract: [Figure not available: see fulltext.]