4-Nitrobiphenyl

Base Information

• Chemical Name: 4-Nitrobiphenyl
• CAS No.: 92-93-3
• Molecular Formula: C12H9 N O2
• Molecular Weight: 199.209
• Hs Code.: 29042090
• European Community (EC) Number: 202-204-7
• ICSC Number: 1395
• NSC Number: 1324
• UN Number: 2811
• UNII: QM80NUW6WZ
• DSSTox Substance ID: DTXSID9041522
• Nikkaji Number: J3.934I
• Wikidata: Q30899078
• Metabolomics Workbench ID: 153314
• ChEMBL ID: CHEMBL352531
• Mol file: 92-93-3.mol

Synonyms:4-nitrobiphenyl;para-nitrobiphenyl

Chemical Property of 4-Nitrobiphenyl

Chemical Property:

• Appearance/Colour: White to yellow needle-like crystalline solid with a sweetish odor.
• Vapor Pressure: 0.000174mmHg at 25°C
• Melting Point: 114 ºC
• Refractive Index: 1.5880 (estimate)
• Boiling Point: 340 ºC
• Flash Point: 43 ºC
• PSA: 45.82000
• Density: 1.328
• LogP: 3.78500
• Solubility.: Soluble in acetic acid, benzene, chloroform, and ether (Weast, 1986)
• Water Solubility.: insoluble
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 199.063328530
• Heavy Atom Count: 15
• Complexity: 210
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

4-Nitrobiphenyl ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Toxic by ingestion and skin contact. TLV: confirmed human carcinogen.
• Hazard Codes: T,N
• Statements: 45-51/53
• Safety Statements: 53-45-61

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitros, Aromatic
• Canonical SMILES: C1=CC=C(C=C1)C2=CC=C(C=C2)[N+](=O)[O-]
• Inhalation Risk: A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.
• Effects of Short Term Exposure: The substance is irritating to the eyes.
• Effects of Long Term Exposure: This substance is probably carcinogenic to humans.
• Uses: Formerly in preparation of p-biphenylamine, q.v. 4-Nitrobiphenyl has some uses as a plasticizer, fungicide, and wood preservative. Formerly used as an intermediate for 4-aminobiphenyl

Technology Process of 4-Nitrobiphenyl

There total 434 articles about 4-Nitrobiphenyl 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: 98.0%

p-nitrobenzene iodide (636-98-6) + triethoxyphenylsilane (780-69-8) → 1-phenyl-4-nitrobenzene (92-93-3)

Guidance literature:

triethoxyphenylsilane; With cesium fluoride; In 1-methyl-pyrrolidin-2-one; at 20 ℃; for 1h;

p-nitrobenzene iodide; With (1-benzyl-4-aza-1-azoniabicyclo[2.2.2]octane)₂Pd₂Cl₆; In 1-methyl-pyrrolidin-2-one; at 20 - 100 ℃; for 0.0166667h; Temperature; Time; Microwave irradiation;

DOI:10.1002/aoc.3100

Reference yield: 97.0%

[2-(hydroxymethyl)phenyl]dimethyl(phenyl)silane (853955-69-8) + p-nitrobenzene iodide (636-98-6) → 1-phenyl-4-nitrobenzene (92-93-3)

Guidance literature:

With potassium carbonate; N-cyclohexyl-1-[2-(diphenylphosphanyl)phenyl]methanimine; palladium dichloride; In water; dimethyl sulfoxide; at 50 ℃; for 13h;

Reference yield: 96.0%

p-nitrobenzene iodide (636-98-6) + triphenylbismuthane (603-33-8) → 1-phenyl-4-nitrobenzene (92-93-3)

Guidance literature:

With potassium fluoride; In dimethyl sulfoxide; at 105 ℃; for 0.25h;

DOI:10.1002/ejoc.200901210

upstream raw materials:

para-nitrophenyl bromide

phenylhydrazine hydrochloride

4-nitrobenzenediazonium tetrafluoroborate

benzenesufonyl hydrazide

Downstream raw materials:

1,2-di([1,1'-biphenyl]-4-yl)diazene oxide

4,4'-hydrazodibiphenyl

4,4'-dinitrobiphenyl

2,4'-dinitrobiphenyl

Refernces

• 1、 MacQuarrie, Stephanie,Horton, J. Hugh,Barnes, Jack,McEleney, Kevin,Loock, Hans-Peter,Crudden, Cathleen M.. "Visual observation of redistribution and dissolution of palladium during the Suzuki-Miyaura reaction". . p. 3279 - 3282. Retrieved 2008.
• 2、 Liu, Jia-Qi,Yang, Jun-Juan,Li, Jun-Fei,Li, Kai,Xiao, Xue-Dong,Bai, Ya-Li,Wang, Jun-Wen. "Catalytic cross-coupling reaction of aryl iodides with triarylbismuths by an N-heterocyclic carbene-PdCl2 based on benzo-9-crown-3 catalyst at room temperature". . p. 125 - 130. Retrieved 2017.
• 3、 Sedghi, Roya,Heidari, Bahareh,Shahmohamadi, Hatef,Zarshenas, Pourya,Varma, Rajender S.. "Pd nanocatalyst adorned on magnetic chitosan?N-Heterocyclic carbene: Eco-compatible suzuki cross-coupling reaction". . . Retrieved 2019.
• 4、 Faria, Vinicius W.,Oliveira, Deyvid G. M.,Kurz, Marcia H. S.,Goncalves, Fabio F.,Scheeren, Carla W.,Rosa, Gilber R.. "Palladium nanoparticles supported in a polymeric membrane: An efficient phosphine-free "green" catalyst for Suzuki-Miyaura reactions in water". . p. 13446 - 13452. Retrieved 2014.
• 5、 Masteri-Farahani, Majid,Niakan, Mahsa. "An efficient clean and sustainable methodology for catalytic C-C coupling process over a Pd-free magnetically recoverable cobalt catalyst". . . Retrieved 2022/03/27.
• 6、 Albano, Gianluigi,Farinola, Gianluca M.,Giannini, Cinzia,Musio, Roberta,Omenetto, Fiorenzo G.,Rizzo, Giorgio,Sibillano, Teresa. "Silk?Fibroin-Supported Palladium Catalyst for Suzuki-Miyaura and Ullmann Coupling Reactions of Aryl Chlorides". . . Retrieved 2022/02/03.