531-91-9 Usage
Description
N,N'-Diphenylbenzidine, also known as diphenylamine, is an organic compound with the chemical formula C6H4(C6H4NH2)2. It is a grey to brownish fine crystalline powder that is commonly used as an indicator in redox titrations and as an intermediate in organic synthesis.
Uses
1. Used in Chemical Analysis:
N,N'-Diphenylbenzidine is used as an indicator for redox titrations, particularly with dichromate or cerium(IV) sulfate. Its ability to change color during the titration process helps in determining the endpoint of the reaction accurately.
2. Used in Organic Synthesis:
N,N'-Diphenylbenzidine serves as an intermediate in the synthesis of various organic compounds. Its unique chemical structure allows it to be a valuable building block in the creation of a wide range of molecules.
3. Used in Dye Manufacturing:
N,N'-Diphenylbenzidine is also utilized in the production of dyes, specifically as a precursor for the synthesis of diphenylamine dyes. These dyes find applications in various industries, including textiles, plastics, and printing.
4. Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, N,N'-Diphenylbenzidine has been historically used in the pharmaceutical industry as a starting material for the synthesis of certain drugs. However, it is important to note that its use in this context has been limited due to concerns about its potential carcinogenic properties.
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%).
Purification Methods
Crystallise the benzidine from toluene or ethyl acetate. Store it in the dark. [Beilstein 13 H 223, 13 IV 368.]
Check Digit Verification of cas no
The CAS Registry Mumber 531-91-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,3 and 1 respectively; the second part has 2 digits, 9 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 531-91:
(5*5)+(4*3)+(3*1)+(2*9)+(1*1)=59
59 % 10 = 9
So 531-91-9 is a valid CAS Registry Number.
531-91-9Relevant articles and documents
The protonation and benzidine rearrangement of tetraphenylhydrazine
Svanholm, Ulla,Parker, Vernon D.
, p. 440 - 441 (1972)
Tetraphenylhydrazine is stable at 0 °C in trifluoroacetic acid-antimony pentafluoride and can be recovered by caustic quench at low temperature but rapidly rearranges to NN'-diphenylbenzidine at room temperature.
Organic electroluminescent compound based on symmetric aromatic amine structure
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Paragraph 0038-0042, (2021/03/24)
The invention discloses an organic electroluminescent compound based on a symmetric aromatic amine structure. The structural formula of the organic electroluminescent compound is shown as a general formula (I) which is described in the specification. The organic electroluminescent compound has the advantages of high glass transition temperature, good thermal stability and high refractive index. When the compound is applied to an organic electroluminescent device, under the same current density, the luminous efficiency is improved to a certain extent, the starting voltage of the device is reduced, the power consumption is relatively reduced, and the service life is correspondingly prolonged.
ORGANIC COMPOUND AND LIGHT EMITTING DIODE AND ORGANIC LIGHT EMITTING DIODE DISPLAY DEVICE USING THE SAME
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Paragraph 0188-0190, (2018/07/28)
The present invention relates to an organic compound in which at least one diphenylmethylene fluorenyl group is directly or indirectly connected to a nitrogen atom constituting at least one amine group. The organic compound according to the present invention has excellent hole injection properties and/or hole transporting properties, and has excellent thermal stability. Accordingly, the organic compound of the present invention, when used in a hole layer, an electron blocking layer and/or a charge generation layer of a light-emitting device, can drive the light-emitting device by securing a sufficient current density at a low voltage. Even when the temperature increases according to driving of the light-emitting device, the compound of the present invention does not become deformed nor degraded, and can reduce stress transferred to the light-emitting device due to low-voltage driving. Accordingly, the organic compound of the present invention can be applied to embody a light-emitting diode and a display device having good luminous efficiency.(110) First electrode(120) Second electrodeCOPYRIGHT KIPO 2018