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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.]
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