2-{[(E)-(2-hydroxyphenyl)methylidene]amino}-5-nitrophenol

Base Information

• Chemical Name: 2-{[(E)-(2-hydroxyphenyl)methylidene]amino}-5-nitrophenol
• CAS No.: 15666-65-6
• Molecular Formula: C13H10 N2 O4
• Molecular Weight: 258.233
• NSC Number: 112429
• DSSTox Substance ID: DTXSID00424828
• Nikkaji Number: J1.701.039E
• Wikidata: Q82237576
• ChEMBL ID: CHEMBL4527165
• Mol file: 15666-65-6.mol

Synonyms:15666-65-6;2-{[(E)-(2-hydroxyphenyl)methylidene]amino}-5-nitrophenol;AC1O6ZRJ;NSC112429;CHEMBL4527165;DTXSID00424828;STL356062;AKOS022141686;NSC-112429;2-(2-Hydroxybenzylideneamino)-5-nitrophenol;2-[(2-Hydroxy-4-Nitrophenyl)aminomethylene]cyclohexa-3,5-dien-1(2H)-one

Chemical Property of 2-{[(E)-(2-hydroxyphenyl)methylidene]amino}-5-nitrophenol

Chemical Property:

• Vapor Pressure: 4.22E-09mmHg at 25°C
• Boiling Point: 460.5°Cat760mmHg
• Flash Point: 232.3°C
• Density: 1.571g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 258.06405680
• Heavy Atom Count: 19
• Complexity: 342

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C(=C1)C=NC2=C(C=C(C=C2)[N+](=O)[O-])O)O

Technology Process of 2-{[(E)-(2-hydroxyphenyl)methylidene]amino}-5-nitrophenol

There total 2 articles about 2-{[(E)-(2-hydroxyphenyl)methylidene]amino}-5-nitrophenol 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: 95.0%

salicylaldehyde (90-02-8) + 5-Nitro-2-aminophenol (121-88-0) → 2-[[(2-hydroxy-4-nitrophenyl)imino]methyl] phenol (15666-65-6)

Guidance literature:

In ethanol; for 2h; Reflux; Inert atmosphere;

DOI:10.1016/j.molcata.2013.04.010

Reference yield:

→ 2-[[(2-hydroxy-4-nitrophenyl)imino]methyl] phenol (15666-65-6)

Guidance literature:

Reference yield: 92.0%

2-[[(2-hydroxy-4-nitrophenyl)imino]methyl] phenol (15666-65-6) + phenylboronic acid (98-80-6) → 2-phenyl-5'-nitrobenzo[d]benzo[h]-6-aza-1,3-dioxa-2-boracyclonon-6-ene (862095-14-5)

Guidance literature:

In tetrahydrofuran; byproducts: H2O; acid (1 equiv.) was added to soln. of ligand (1 equiv.) in THF; mixt. was refluxed for 1 h with Dean-Stark trap; filtered; washed (EtOAc/hexane, 1/9); elem. anal.;

DOI:10.1016/j.jorganchem.2005.03.024

upstream raw materials:

salicylaldehyde

5-Nitro-2-aminophenol

Downstream raw materials:

2-phenyl-5'-nitrobenzo[d]benzo[h]-6-aza-1,3-dioxa-2-boracyclonon-6-ene

phenyl[2-(2'-hydroxyphenyl-O)-4-(3'-cyclohexenyl)-6-nitro-8-quinolate-O',N]boron

Refernces

• 1、 García-González, Ma. Carmen,González-Zamora, Eduardo,Santillan, Rosa,Farfán, Norberto. "Synthesis of 2-imino-3-aminobenzofurans via multicomponent reactions from TosMIC". experimental part. p. 308 - 310. Retrieved 2011/04/12.