N,N'-Diphenylbenzidine

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N,N'-Diphenylbenzidine Basic information

Product Name: N,N'-Diphenylbenzidine

Synonyms: N,N'-DIPHENYLBENZIDINE;N,N'-DIPHENYL BIPHENYLAMINE;N'-Diphenylbenzidine;4-(4-anilinophenyl)-N-phenylaniline;N,N'-Diphenylbenzidine, 97%, indicator;Benzidine, N,N'-diph;N,N'-(1,1'-Biphenyl-4,4'-diyl)bisaniline;N,N'-Diphenyl-1,1'-biphenyl-4,4'-diamine

CAS: 531-91-9

MF: C24H20N2

MW: 336.43

EINECS: 208-521-7

Product Categories: C20 to C30+;Analytical Reagents;Analytical/Chromatography;Building Blocks;Chemical Synthesis;Nitrogen Compounds;Aromatic Phenylacetic Acids and Derivatives;Biphenyls (for High-Performance Polymer Research);Functional Materials;Reagent for High-Performance Polymer Research;C11 to C38Titration;Organic Building Blocks;Redox Indicators;Titration;Amines;Indicators;Nitrogen Compounds;Redox Indicators;531-91-9

Mol File: 531-91-9.mol

N,N'-Diphenylbenzidine Structure

N,N'-Diphenylbenzidine Chemical Properties

Melting point 246-248 °C(lit.)

Boiling point 462.9°C (rough estimate)

density 1.1750 (rough estimate)

vapor density 11.6 (vs air)

refractive index 1.7620 (estimate)

Fp >110°C

storage temp. Store below +30°C.

solubility Acetone (Slightly), DMF (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, Sonicated)

form Fine Crystalline Powder

pka 1.31±0.40(Predicted)

color Gray to brownish

Water Solubility Insoluble in water.

Sensitive Light Sensitive

Merck 14,3319

BRN 2220993

InChIKey FDRNXKXKFNHNCA-UHFFFAOYSA-N

CAS DataBase Reference 531-91-9(CAS DataBase Reference)

NIST Chemistry Reference [1,1'-Biphenyl]-4,4'-diamine, n,n'-diphenyl-(531-91-9)

EPA Substance Registry System [1,1'-Biphenyl]-4,4'-diamine, N,N'-diphenyl- (531-91-9)

Safety Information

Hazard Codes Xi

Safety Statements 22-24/25

RIDADR 2811

WGK Germany 3

F 8

TSCA Yes

HazardClass 6.1(b)

PackingGroup III

HS Code 29215900

MSDS Information

Provider Language

SigmaAldrich English

ACROS English

ALFA English

N,N'-Diphenylbenzidine Usage And Synthesis

Chemical Properties GREY TO BROWNISH FINE CRYSTALLINE POWDER

Uses See diphenylamine.

Uses N,N'-Diphenylbenzidine is an indicator suitable for redox titrations, e.g. with dichromate or cerium(IV) sulfate 1,2. It is also used as intermediates in organic synthesis.

Synthesis The synthesis of N,N'-Diphenylbenzidine is as follows:

3.12 g (10mmol) of 4,4'-dibromodiphenyl, 2.3 mL (25 mmol) of aniline, 2.9 g (30 mmol) of t-BuONa, 183 mg (0.2 mmol) of Pd2(dba)3, and 20 mg (0.1 mmol) of P(t-Bu)3 were dissolved in 30 mL of toluene, and then stirred at 90°C for 3 hrs. The reaction mixture was cooled to room temperature and three times extracted with distilled water and diethyl ether. Precipitates in an organic layer were filtered, washed with acetone and diethyl ether, and then dried in vacuum to obtain 0.3g of the intermediate compound C (yield: 90%). synthesis of N,N'-Diphenylbenzidine.png

Purification Methods Crystallise the benzidine from toluene or ethyl acetate. Store it in the dark. [Beilstein 13 H 223, 13 IV 368.]