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Chemical structure of N.N’-Diphenylbenzidine | 531-91-9
CAS: 531-91-9
SKU: S1484
N.N’-Diphenylbenzidine | SKU: S1484
synonyms: DPB; N,N′-Diphenylbenzidine; N4,N4′-Diphenyl-[1,1′-biphenyl]-4,4′-diamine; 4,4′-Bis(phenylamino)biphenyl; N,N′-Diphenyl-4,4′-diaminobiphenyl
Chemical structure of N.N’-Diphenylbenzidine | 531-91-9
N,N′-Diphenylbenzidine (DPB, N4,N4′-diphenylbiphenyl-4,4′-diamine, 4,4′-bis(phenylamino)biphenyl; C24H20N2) is a biphenyl core with a phenylamino group at each para position. It has a molecular weight of 336.43 g/mol and is supplied as a high-melting powder (melting point about 242–248 °C) with an assay of at least 98% by HPLC and suitability for titration use. Its main commercial importance is in organic electronics. N,N′-Diphenylbenzidine is the parent diarylamine of the benzidine-type hole-transport materials used in organic light-emitting diodes: N-arylation of its two N–H groups under Buchwald–Hartwig or Ullmann conditions gives compounds such as TPD and NPB, which are benchmark hole-transport layer materials. The compound itself is described as a building block for the preparation of hole-transporting materials for organic LEDs. In analytical chemistry, diphenylbenzidine is a classic redox indicator, and the product is listed as suitable for titration. Sarchem Labs offers N,N′-diphenylbenzidine (SKU S1484) for organic-electronics, materials and analytical customers. Each lot ships with a Certificate of Analysis and Safety Data Sheet, and laboratory to bulk quantities can be quoted on request.
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Specifications

Melting Point242°C
ColorUndesignated
Linear Formula4-(C6H5NH)C6H4C6H4-4-(NHC6H5)
Quantity5g
Formula Weight336.44
percent purity≥98.0% (HPLC,N)
Physical FormCrystal-Powder at 20°C
Chemical Name or MaterialN,N′-Diphenylbenzidine (N4,N4′-diphenylbiphenyl-4,4′-diamine)
Molecular Weight336.43 g/mol
SMILES StringN(c1ccccc1)c2ccc(cc2)-c3ccc(Nc4ccccc4)cc3
Assay≥98.0% (HPLC)
CAS Number531-91-9
EC Number208-521-7
Empirical FormulaC24H20N2
NACRESNA.22
PubChem Substance ID24893610
UNSPSC Code12352100
MDL NumberMFCD00003016
InChI1S/C24H20N2/c1-3-7-21(8-4-1)25-23-15-11-19(12-16-23)20-13-17-24(18-14-20)26-22-9-5-2-6-10-22/h1-18,25-26H
InChI KeyFDRNXKXKFNHNCA-UHFFFAOYSA-N
PubChem CID68280
Beilstein/REAXYS Number2220993
Quality Level100
Technique SuitabilityTitration
FormPowder (crystal-powder)

Applications

No Application Found
Organic electronics research: a starting diarylamine for triarylamine-based hole-injection and hole-transport layers and related electroactive materials.
Redox indicator and titration reagent: a classic redox indicator in analytical titrations; its oxidised form is intensely coloured (blue-violet), which signals the end point.
Polymer and dye intermediates: a bis(diarylamine) monomer for conjugated polymers and electroactive materials.
Antioxidant and radical-trapping studies: diarylamines of this type are model hydrogen-atom donors in studies of radical scavenging.

Product Description

What is N,N′-Diphenylbenzidine?

N,N′-Diphenylbenzidine is a symmetrical secondary diarylamine: benzidine (4,4′-diaminobiphenyl) in which each primary amino group has been arylated once. Its formula is C24H20N2 and its molecular weight is 336.43 g/mol. The two N–H groups are the reactive handles for further arylation, and the extended conjugation across the biphenyl bridge is what gives the benzidine-type hole-transport materials their low ionisation potential. It should not be confused with benzidine itself, with N,N,N′,N′-tetraphenylbenzidine or with N,N′-diphenyl-p-phenylenediamine (DPPD).

Uses of N,N′-Diphenylbenzidine

In the OLED and photovoltaic industries, N,N′-diphenylbenzidine is a precursor of the hole-transport layer: Buchwald–Hartwig coupling with an aryl bromide or iodide installs the two additional aryl groups to give materials such as TPD (with 3-methylphenyl groups) and NPB (with 1-naphthyl groups). In analytical chemistry, its oxidation to a coloured product is used to signal redox end points.

Buying and Handling Considerations

The grade offered is at least 98.0% by HPLC. For device-grade materials, ask for the Certificate of Analysis of the lot and for the impurity profile, because trace halide, metal and mono-arylated by-products affect device lifetime; tell us if you need a sublimed or higher-purity grade. Store in a tightly closed container in a cool, dry place away from light, strong oxidisers and strong acids. As with all aromatic amines, minimise dust exposure and skin contact.

Safety Information

  • Hazard Classification: No GHS pictogram or hazard statement is published for this compound
  • Storage Class: 11 – Combustible solids | WGK: 3 | Flash Point: not applicable
  • PPE: Type N95 (US) dust mask, eyeshields, gloves

Although no hazard classification is published, treat it as a combustible aromatic-amine powder: avoid generating dust, avoid contact with skin and eyes, and wash hands thoroughly after use.

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No related products found.

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FAQs: N.N’-Diphenylbenzidine

It is used as a building block for hole-transport materials in organic LEDs and other organic electronics, and as a redox indicator in analytical titrations.

No. Benzidine is the parent diamine with free NH2 groups. N,N′-Diphenylbenzidine (CAS 531-91-9) carries a phenyl group on each nitrogen. Check the CAS number when ordering.

By N-arylation of the two N–H groups, for example Buchwald–Hartwig coupling with 3-iodotoluene or Ullmann coupling to give TPD, and coupling with 1-bromonaphthalene to give NPB.

The formula is C24H20N2, the molecular weight is 336.43 g/mol and the melting point is about 242 °C. The assay is at least 98.0% by HPLC.

No hazard classification is published, but it is an aromatic amine powder. Avoid dust and contact with skin and eyes and wear gloves, eye protection and a dust mask.

Keep it tightly closed in a cool, dry place away from light, strong oxidisers and acids.

Yes. Each lot of SKU S1484 ships with a Certificate of Analysis and Safety Data Sheet, and Sarchem Labs quotes laboratory to bulk quantities.