4'-Nitro-3-biphenylol

Base Information

• Chemical Name: 4'-Nitro-3-biphenylol
• CAS No.: 28023-89-4
• Molecular Formula: C₁₂H₉NO₃
• Molecular Weight: 215.208
• DSSTox Substance ID: DTXSID10577839
• Nikkaji Number: J392.704K
• Wikidata: Q82467956
• Mol file: 28023-89-4.mol

Synonyms:4'-Nitro-3-biphenylol;28023-89-4;3-(4-nitrophenyl)phenol;4'-NITROBIPHENYL-3-OL;DTXSID10577839;4'-Nitro[1,1'-biphenyl]-3-ol;AKOS015961117;AC-12966;EN300-840319;J-016949

Chemical Property of 4'-Nitro-3-biphenylol

Chemical Property:

• Vapor Pressure: 1.69E-07mmHg at 25°C
• Melting Point: 184-186 °C (sublm)
• Refractive Index: 1.637
• Boiling Point: 415.6°C at 760 mmHg
• PKA: 9.40±0.10(Predicted)
• Flash Point: 181.9°C
• PSA: 66.05000
• Density: 1.304g/cm³
• LogP: 3.49060
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 215.058243149
• Heavy Atom Count: 16
• Complexity: 243

Purity/Quality:

98%min ^*data from raw suppliers

4'-NITRO-3-BIPHENYLOL 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of 4'-Nitro-3-biphenylol

There total 4 articles about 4'-Nitro-3-biphenylol 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: 60.0%

p-nitrobenzene iodide (636-98-6) + salicylic acid (69-72-7,25496-36-0,8052-31-1) → 4'-nitro-[1,1'-biphenyl]-3-ol (28023-89-4)

Guidance literature:

With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; potassium carbonate; silver carbonate; In acetic acid; at 150 ℃; for 16h;

DOI:10.1039/c4cc09674f

Reference yield: 54.0%

p-nitrobenzene iodide (636-98-6) + phenol (108-95-2,27073-41-2) → 4'-nitro-[1,1'-biphenyl]-3-ol (28023-89-4)

Guidance literature:

phenol; With potassium hydroxide; In toluene; at 50 ℃; for 0.166667h;

With carbon dioxide; at 190 ℃; for 2h; under 19001.3 Torr; Inert atmosphere; Autoclave;

p-nitrobenzene iodide; With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II) dichloride; acetic acid; silver carbonate; at 130 ℃; for 16h; under 19001.3 Torr; Reagent/catalyst; regioselective reaction; Inert atmosphere; Autoclave;

DOI:10.1021/ja500457s

Reference yield: 52.0%

1-(2-oxopropyl)pyridinium chloride (42508-60-1) + 3-dimethylamino-1-(4-nitrophenyl)propan-1-one hydrochloride (36994-29-3) → 4'-nitro-[1,1'-biphenyl]-3-ol (28023-89-4)

Guidance literature:

With triethylamine; In ethanol; for 2h; Heating;

DOI:10.1055/s-1991-26540

upstream raw materials:

1-(2-oxopropyl)pyridinium chloride

3-dimethylamino-1-(4-nitrophenyl)propan-1-one hydrochloride

p-nitrobenzene iodide

phenol

Refernces

• 1、 Luo, Junfei,Preciado, Sara,Larrosa, Igor. "Salicylic acids as readily available starting materials for the synthesis of meta-substituted biaryls". supporting information. p. 3127 - 3130. Retrieved 2015/06/03.
• 2、 Eichinger,Nussbaumer. "Syntheses of 3-arylphenols from (3-aryl-3-oxopropyl)dialkylammonium chlorides and 1-(2-Oxopropyl)pyridinium chloride". . p. 663 - 664. Retrieved 2007/10/02.