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.
Arylamine compound of imidazopyridine, and application thereof
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Paragraph 0053-0056, (2021/06/12)
The invention relates to an arylamine compound ofimidazopyridine, and application thereof. The compound has a structure as shown in a formula (I). The compound disclosed by the invention has the advantages of low sublimation temperature, good thermal stability, high refractive index, small refractive index difference in a visible region and the like, can be used as a light extraction layer material and is applied to an organic light-emitting device.
Aromatic amine derivative and organic light-emitting device using same
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Paragraph 0061-0063, (2018/03/01)
The invention provides an aromatic amine derivative and an organic light-emitting device using the same and relates to the technical field of organic optoelectronic materials. Carbazole structures have higher redox potential values and good stability under air or illumination conditions. Therefore, by introducing the carbazole structures, the obtained aromatic amine derivative disclosed by the invention shows good thermal stability, can be used for preparing the organic light-emitting device and particularly shows the advantages of high efficiency and low driving voltage when being used as a hole transmission material in the organic light-emitting device; the aromatic amine derivative is an organic light-emitting material with excellent performance; the organic light-emitting device disclosed by the invention is superior to an existing common OLED (Organic Light Emitting Diode) device.