2-(Benzyloxy)-4-nitroaniline

Base Information

• Chemical Name: 2-(Benzyloxy)-4-nitroaniline
• CAS No.: 25945-96-4
• Molecular Formula: C13H12N2O3
• Molecular Weight: 244.25
• Hs Code.: 2922199090
• DSSTox Substance ID: DTXSID70379699
• Nikkaji Number: J3.464.986C
• Wikidata: Q82169627
• Mol file: 25945-96-4.mol

Synonyms:2-(benzyloxy)-4-nitroaniline;25945-96-4;4-nitro-2-phenylmethoxyaniline;2-Benzyloxy-4-nitrophenylamine;Benzenamine, 4-nitro-2-(phenylmethoxy)-;2-benzyloxy-4-nitroaniline;ghl.PD_Mitscher_leg0.610;SCHEMBL3298587;2-benzyloxy-4-nitro-phenylamine;4-nitro-2-phenylmethoxy-aniline;DTXSID70379699;OTBQGZCBYVALOL-UHFFFAOYSA-N;MFCD00276800;BS-16791;CS-0156197;FT-0638558;D82034;A818098;AE-562/12222111

Chemical Property of 2-(Benzyloxy)-4-nitroaniline

Chemical Property:

• Vapor Pressure: 9.19E-09mmHg at 25°C
• Melting Point: 150.5-151.5 °C(Solv: ethanol (64-17-5))
• Boiling Point: 463.3°C at 760 mmHg
• PKA: 0.55±0.36(Predicted)
• Flash Point: 234°C
• PSA: 81.07000
• Density: 1.297g/cm³
• LogP: 3.86040
• Storage Temp.: 2-8°C(protect from light)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 244.08479225
• Heavy Atom Count: 18
• Complexity: 274

Purity/Quality:

98%min ^*data from raw suppliers

2-Benzyloxy-4-nitrophenylamine 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC2=C(C=CC(=C2)[N+](=O)[O-])N

Technology Process of 2-(Benzyloxy)-4-nitroaniline

There total 4 articles about 2-(Benzyloxy)-4-nitroaniline 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: 98.5%

benzyl bromide (100-39-0) + 5-Nitro-2-aminophenol (121-88-0) → 2-benzyloxy-4-nitro-phenylamine (25945-96-4)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 20h;

DOI:10.1021/acs.joc.5b01373

Reference yield: 94.0%

benzyl chloride (100-44-7) + 5-Nitro-2-aminophenol (121-88-0) → 2-benzyloxy-4-nitro-phenylamine (25945-96-4)

Guidance literature:

With potassium carbonate; potassium iodide; In N,N-dimethyl-formamide; at 25 ℃; for 24h;

DOI:10.1021/ja953777e

Reference yield:

N-(2-(benzyloxy)phenyl)acetamide (34288-19-2) → 2-benzyloxy-4-nitro-phenylamine (25945-96-4) + acetic acid-(2-benzyloxy-5-nitro-anilide) (195882-75-8)

Guidance literature:

With water; nitric acid; at 0 ℃; Erwaermen des Reaktionsprodukts mit Natriumaethylat in Aethanol;

upstream raw materials:

N-(2-(benzyloxy)phenyl)acetamide

benzyl chloride

5-Nitro-2-aminophenol

benzyl bromide

Downstream raw materials:

C₁₅H₁₈N₂O₃S

N,N-(2-hydroxy-4-nitrophenyl)dimethanesulfonamide

Refernces

• 1、 Stephenson, Michael J.,Howell, Lesley A.,O'Connell, Maria A.,Fox, Keith R.,Adcock, Claire,Kingston, Jenny,Sheldrake, Helen,Pors, Klaus,Collingwood, Stephen P.,Searcey, Mark. "Solid-Phase Synthesis of Duocarmycin Analogues and the Effect of C-Terminal Substitution on Biological Activity". . p. 9454 - 9457. Retrieved 2015.
• 2、 -. "SYNTHESIS OF DUOCARMYCIN ANALOGUES". Page/Page column 27; 28. . Retrieved 2016/12/22.