4,4'-Diphenoxy-1,1'-biphenyl

Base Information

• Chemical Name: 4,4'-Diphenoxy-1,1'-biphenyl
• CAS No.: 2519-16-6
• Molecular Formula: C24H18 O2
• Molecular Weight: 338.406
• NSC Number: 168738
• DSSTox Substance ID: DTXSID80304997
• Nikkaji Number: J1.809.755I
• Wikidata: Q82051386
• Mol file: 2519-16-6.mol

Synonyms:4,4'-Diphenoxy-1,1'-biphenyl;2519-16-6;4,4'-diphenoxybiphenyl;NSC168738;1-phenoxy-4-(4-phenoxyphenyl)benzene;4,4'-Diphenoxy biphenyl;SCHEMBL197414;DTXSID80304997;NSC 168738;NSC-168738;4,?4'-?Diphenoxy-?1,?1'-?biphenyl;AS-78008;D94358

Chemical Property of 4,4'-Diphenoxy-1,1'-biphenyl

Chemical Property:

• XLogP3: 6.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 338.130679813
• Heavy Atom Count: 26
• Complexity: 343

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)OC2=CC=C(C=C2)C3=CC=C(C=C3)OC4=CC=CC=C4

Technology Process of 4,4'-Diphenoxy-1,1'-biphenyl

There total 20 articles about 4,4'-Diphenoxy-1,1'-biphenyl 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%

4,4'-diiodobiphenyl (3001-15-8) + phenol (108-95-2,27073-41-2) → 4,4'-diphenoxy-1,1'-biphenyl (2519-16-6)

Guidance literature:

With copper(l) iodide; iron(III)-acetylacetonate; potassium carbonate; In dimethyl sulfoxide; at 140 ℃; for 48h; Inert atmosphere;

DOI:10.1039/c1ob05155e

Reference yield: 96.0%

4,4'-bis((η6-phenoxy-η5-cyclopentadienyl)iron)biphenyl hexafluorophosphate → ferrocene (102-54-5,55404-68-7) + 4,4'-diphenoxy-1,1'-biphenyl (2519-16-6)

Guidance literature:

In dichloromethane; acetonitrile; Irradiation (UV/VIS); addn. of diiron-complex dissolved in CH2Cl2/CH3CN to a photolysis tube, purging with N2 for 30 min, irradiation under intense visible light (Xenon lamp) for 4 h; concn. by evapn. under reduced pressure, column chromy., elution (hexane) gives yellow band of ferrocene, elution (hexane/CHCl3) gives benzene-compd., evapn. to dryness, elem. anal.;

DOI:10.1021/om00013a055

Reference yield: 95.0%

4-phenoxyphenylboronic acid (51067-38-0) → 4,4'-diphenoxy-1,1'-biphenyl (2519-16-6)

Guidance literature:

With oxygen; sodium acetate; palladium diacetate; In water; at 23 ℃; for 10h;

DOI:10.1016/S0040-4039(02)01894-4

upstream raw materials:

n-butyllithium

4-Bromodiphenyl ether

diethyl ether

iodobenzene

Downstream raw materials:

4,4'-Bis-<4-acetyl-phenoxy>-biphenyl

Refernces

• 1、 Qrareya, Hisham,Meazza, Lorenzo,Protti, Stefano,Fagnoni, Maurizio. "Metal-free synthesis of biarenes via photoextrusion in di(tri)aryl phosphates". supporting information. p. 3008 - 3014. Retrieved 2021/01/18.
• 2、 Dzhevakov, Pavel B.,Topchiy, Maxim A.,Zharkova, Daria A.,Morozov, Oleg S.,Asachenko, Andrey F.,Nechaev, Mikhail S.. "Miyaura Borylation and One-Pot Two-Step Homocoupling of Aryl Chlorides and Bromides under Solvent-Free Conditions". . p. 977 - 983. Retrieved 2016/04/05.