N,N,N',N'-Tetraphenylbenzidine

Base Information

• Chemical Name: N,N,N',N'-Tetraphenylbenzidine
• CAS No.: 15546-43-7
• Molecular Formula: C36H28N2
• Molecular Weight: 488.632
• Hs Code.: 29215900
• European Community (EC) Number: 239-599-0
• DSSTox Substance ID: DTXSID2065913
• Nikkaji Number: J317.905B
• Wikidata: Q72507880
• Mol file: 15546-43-7.mol

Synonyms:tetraphenylbenzidine;triphenyl diamine

Chemical Property of N,N,N',N'-Tetraphenylbenzidine

Chemical Property:

• Appearance/Colour: white crystalline powder
• Melting Point: 230-234 °C
• Boiling Point: 649.7 °C at 760 mmHg
• PKA: -2.62±0.60(Predicted)
• Flash Point: 291.2 °C
• PSA: 68.25000
• Density: 1.171 g/cm³
• LogP: 4.27640
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 10
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 7
• Exact Mass: 488.225248902
• Heavy Atom Count: 38
• Complexity: 557

Purity/Quality:

99% ^*data from raw suppliers

N,N,N'',N''-Tetraphenylbenzidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)N(C2=CC=CC=C2)C3=CC=C(C=C3)C4=CC=C(C=C4)N(C5=CC=CC=C5)C6=CC=CC=C6

Technology Process of N,N,N',N'-Tetraphenylbenzidine

There total 35 articles about N,N,N',N'-Tetraphenylbenzidine 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: 99.0%

N,N-diphenylaminobenzene (603-34-9) → N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl (15546-43-7)

Guidance literature:

N,N-diphenylaminobenzene; With methanesulfonic acid; In dichloromethane; at 0 ℃;

With chloranil; In dichloromethane; at 0 - 20 ℃; for 0.0166667h; Reagent/catalyst; Solvent; Time;

DOI:10.1021/acs.joc.7b01377

Reference yield: 93.0%

bromobenzene (108-86-1,52753-63-6) + p,p'-diaminobiphenyl (92-87-5) → N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl (15546-43-7)

Guidance literature:

With bis-triphenylphosphine-palladium(II) chloride; triphenylphosphine; sodium t-butanolate; In o-xylene; at 144 ℃; for 48h; Inert atmosphere; Schlenk technique;

DOI:10.1016/j.tet.2014.05.048

Reference yield: 93.0%

4,4'-diaminobiphenyl hydrochloride (75752-15-7) + chlorobenzene (108-90-7) → N,N,N',N'-tetraphenyl-4,4'-diaminobiphenyl (15546-43-7)

Guidance literature:

4,4'-diaminobiphenyl hydrochloride; With sodium hydride; In o-xylene; at 25 ℃; for 0.5h; Schlenk technique;

chlorobenzene; With bis-triphenylphosphine-palladium(II) chloride; (E)-2-(((2,5-bis(trifluoromethyl)phenyl)imino)methyl)phenol; sodium t-butanolate; at 145 ℃; for 24h; Schlenk technique; Inert atmosphere;

DOI:10.1002/cjoc.201700276

upstream raw materials:

N,N-diphenylaminobenzene

4,4'-diiodobiphenyl

diphenylamine

iodobenzene

Downstream raw materials:

N,N,N',N'-tetraphenylbenzidine

-diphenylammoniumyl

C₆₄H₃₆F₂₄N₁₀O₈

N,N,N′,N′-tetrakis(4-bromophenyl)[1,1′-biphenyl]-4,4′-diamine

Refernces

Anodic oxidation of novel hole-transporting materials derived from tetraarylbenzidines. Electrochemical and spectroscopic characterization

10.1135/cccc20001403

The purpose of the study was to prepare fluorenylidene-linked triarylamines using the palladium-catalyzed Hartwig–Buchwald amination and investigate their redox and spectral properties. The researchers synthesized compounds 4 and 5, which contain two hole-transporting units linked by a non-conjugated fluorene bridge, aiming to improve the thermal and film-forming properties of OLED materials while preserving their electronic characteristics. The study concluded that these linked triarylamines showed significantly increased glass-transition temperatures compared to low-molecular-weight analogues conventionally used in OLEDs, with their desirable electronic properties intact. The research involved the use of various chemicals, including N,N,N′,N′-tetraphenylbenzidine (TPB), N,N′-di(1-naphthyl)-N,N′-diphenylbenzidine (α-NPD), triphenylamine (TPA), and tetraarylbenzidine derivatives, as well as palladium catalysts and other reagents necessary for the Hartwig–Buchwald amination process.