N,N'-Diphenylbenzidine

Synonym(s):N,N′-Diphenyl-4,4′-diaminobiphenyl, N,N′-Diphenyl-[1,1′-biphenyl]-4,4′-diamine;N,N′-Diphenylbenzidine

CAS NO.：531-91-9
Empirical Formula: C24H20N2
Molecular Weight: 336.43
MDL number: MFCD00003016
EINECS: 208-521-7
SAFETY DATA SHEET (SDS)
Update Date: 2024-12-19 15:48:47

What is N,N'-Diphenylbenzidine?

Chemical properties

GREY TO BROWNISH FINE CRYSTALLINE POWDER

The Uses of N,N'-Diphenylbenzidine

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.

The Uses of N,N'-Diphenylbenzidine

See diphenylamine.

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.]

Properties of N,N'-Diphenylbenzidine

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)
Flash point:	>110°C
storage temp.	Store below +30°C.
solubility	Acetone (Slightly), DMF (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly, So
pka	1.31±0.40(Predicted)
form	Fine Crystalline Powder
color	Gray to brownish
Water Solubility	Insoluble in water.
Sensitive	Light Sensitive
Merck	14,3319
BRN	2220993
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 for N,N'-Diphenylbenzidine

Signal word	Warning
Pictogram(s)	Exclamation Mark Irritant GHS07 Health Hazard GHS08
GHS Hazard Statements	H351:Carcinogenicity
Precautionary Statement Codes	P201:Obtain special instructions before use. P202:Do not handle until all safety precautions have been read and understood. P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P264:Wash hands thoroughly after handling. P264:Wash skin thouroughly after handling. P270:Do not eat, drink or smoke when using this product. P271:Use only outdoors or in a well-ventilated area. P280:Wear protective gloves/protective clothing/eye protection/face protection. P308+P313:IF exposed or concerned: Get medical advice/attention. P405:Store locked up. P501:Dispose of contents/container to..…