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101-54-2

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101-54-2 Usage

Description

p-Aminodiphenylamine hydrochloride was formerly used as a hair dye. Sensitization, when deteeted by patch testing, is relatively low in hairdressers.

Chemical Properties

Dark grey flake

Uses

Different sources of media describe the Uses of 101-54-2 differently. You can refer to the following data:
1. Dye intermediate, pharmaceuticals, photographic chemicals.
2. 4-Aminodiphenylamine is used as an oxidation dye color in hair dyes. It is also promoted as an efficient reagent for oxidase enzymes, including glucose, lactate, xanthine, and lysine oxidases.
3. p-Anilinoaniline is an antioxidant that has shown to cause a reduction of NOx emissions from soybean biodiesel powered DI diesel engines but has increased CO and HC emissions. It is also used to produce dyes, pharmaceuticals, and photographic chemicals and frmerly used as a hair dye.

Definition

ChEBI: An aromatic amine that is the 4-amino derivative of diphenylamine.

General Description

Odorless purple-black solid or flake or dark purple chips.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Aminodiphenylamine is incompatible with strong oxidizers. 4-Aminodiphenylamine is also incompatible with strong acids. 4-Aminodiphenylamine may react with plastics.

Fire Hazard

4-Aminodiphenylamine is combustible.

Contact allergens

This substance was formerly used as a hair dye. Sensitization, when detected by patch testing, is relatively low in hairdressers.

Purification Methods

It crystallises from EtOH with m 66o, and from ligroin with m 75o. It can be distilled at high vacuum. [Beilstein 13 IV 113.]

Check Digit Verification of cas no

The CAS Registry Mumber 101-54-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,0 and 1 respectively; the second part has 2 digits, 5 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 101-54:
(5*1)+(4*0)+(3*1)+(2*5)+(1*4)=22
22 % 10 = 2
So 101-54-2 is a valid CAS Registry Number.
InChI:InChI=1/C12H12N2/c13-14(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10H,13H2

101-54-2 Well-known Company Product Price

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  • Alfa Aesar

  • (B23867)  N-Phenyl-p-phenylenediamine, 98%   

  • 101-54-2

  • 100g

  • 206.0CNY

  • Detail
  • Alfa Aesar

  • (B23867)  N-Phenyl-p-phenylenediamine, 98%   

  • 101-54-2

  • 250g

  • 509.0CNY

  • Detail
  • Alfa Aesar

  • (B23867)  N-Phenyl-p-phenylenediamine, 98%   

  • 101-54-2

  • 1000g

  • 1149.0CNY

  • Detail
  • Aldrich

  • (241393)  N-Phenyl-p-phenylenediamine  98%

  • 101-54-2

  • 241393-100G

  • 230.49CNY

  • Detail
  • Aldrich

  • (241393)  N-Phenyl-p-phenylenediamine  98%

  • 101-54-2

  • 241393-1KG

  • 789.75CNY

  • Detail

101-54-2SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name p-aminodiphenylamine

1.2 Other means of identification

Product number -
Other names N-Phenyl-1,4-phenylenediamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only. Intermediates
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:101-54-2 SDS

101-54-2Relevant articles and documents

Synthesis and properties of 4-[(E)-(4'-R-phenyl)diazenyl]phthalonitriles and cobalt phthalocyanines obtained therefrom

Tikhomirova,Gruzdeva,Shaposhnikov

, p. 2778 - 2785 (2015)

The diazotization-azocoupling method has been utilized to prepare a series of previously unknown 4-[(E)-(4'-R-phenyl)diazenyl]phthalonitriles, which were further transformed into the corresponding cobalt phthalocyanines. The effect of the peripheral substitution of the phthalocyanine ligand on the spectral properties of the prepared compounds has been demonstrated.

Preparation of N-phenyl-p-phenylenediamine by coupling of aniline and nitrobenzene in KOH–poly(ethylene glycol) medium

Babkin, Alexander V.,Asachenko, Andrey F.,Uborsky, Dmitry V.,Kononovich, Dmitry S.,Izmer, Vyatcheslav V.,Kudakina, Vera A.,Shnaider, Viktoriya A.,Shevchenko, Nikolay E.,Voskoboynikov, Alexander Z.

, p. 555 - 557 (2016)

A novel protocol for efficient coupling of nitrobenzene and aniline in poly(ethylene glycol) medium in the presence of KOH giving diphenylamine derivatives has been developed, to enable the exclusion of the toxic tetramethylammonium hydroxide catalyst commonly used in the rubber antidegradant industry.

2,6-Bis(diphenylphosphino)pyridine: A simple ligand showing high performance in palladium-catalyzed CN coupling reactions

Nadri, Shirin,Rafiee, Ezzat,Jamali, Sirous,Joshaghani, Mohammad

, p. 4098 - 4101 (2014)

The use of commercially available 2,6-bis(diphenylphosphino)pyridine as a ligand in conjunction with K2CO3, DMAc and TBAB is an effective method for the palladium-catalyzed CN coupling of a variety of aryl halides with anilines, N-heterocyclic aromatic amines, and a cyclic secondary amine. The reactions proceed in good to excellent yield (up to 98%) while the loading of Pd(OAc)2 was as low as 0.025 mol %.

Gold(I)-mediated rearrangement of 1,2-diphenylhydrazine to semidines

Xia, Aibing,James, Alan J.,Sharp, Paul R.

, p. 451 - 453 (1999)

Reaction of 1,2-diphenylhydrazine with the gold oxo complex [(PPh3Au)3(μ-O)]BF4 gives a mixture of [(Ph3PAu)3(μ-N-1,4-C6H 4-NHPh)]BF4 (1; 82%) and [(Ph3PAu)3(μ-N-1,2-C6H 4-NHPh)]BF4 (2; 18%) in CH2-Cl2 at ambient temperature, A crossover experiment using a 1:1 mixture of 1,2-diphenylhydrazine and 1,2-diphenylhydrazine-d10 indicates that the rearrangement process is intramolecular.

Heterogeneous Catalytic Transfer Hydrogenation of 4-Nitrodiphenylamine to p-Phenylenediamines

Banerjee, Ankur A.,Mukesh, Doble

, p. 1275 - 1276 (1988)

p-Phenylenediamine analogues have been prepared from 4-nitrodophenylamine (1) by catalytic transfer hydrogenation in one stage; the process can be extended to the general condensation of a nitro compound with an alcohol (with Raney nickel as catalyst) or a ketone (with palladium as catalyst).

EPR and pulsed ENDOR study of intermediates from reactions of aromatic azides with group 13 metal trichlorides

Bencivenni, Giorgio,Cesari, Riccardo,Nanni, Daniele,El Mkam, Hassane,Walton, John C.

, p. 713 - 725 (2010)

The reactions of group 13 metal trichlorides with aromatic azides were examined by CW EPR and pulsed ENDOR spectroscopies. Complex EPR spectra were obtained from reactions of aluminium, gallium and indium trichlorides with phenyl azides containing a variety of substituents. Analysis of the spectra showed that 4-methoxy-, 3-methoxy- and 2-methoxyphenyl azides all gave 'dimer' radical cations [ArNHC6H4NH2]+ and trimers [ArNHC6H4NHC6H4NH 2]+ followed by polymers. 4-Azidobenzonitrile, with its electron-withdrawing substituent, did not react. In general the aromatic azides appeared to react most rapidly with AlCl3 but this reagent tended to generate much polymer. InCl3 was the least reactive group 13 halide. DFT computations of the radical cations provided corroborating evidence and suggested that the unpaired electrons were accommodated in extensive π-delocalised orbitals. A mechanism to account for the reductive conversion of aromatic azides to the corresponding anilines and thence to the dimers and trimers is proposed.

Nickel(0)/N-heterocyclic carbene complexes catalysed arylation of aromatic diamines

Kuhl, Sébastien,Fort, Yves,Schneider, Rapha?l

, p. 6169 - 6177 (2005)

Nickel complexes of N-heterocyclic carbenes were examined for effecting C-N coupling reactions between aromatic diamines and aryl chlorides of varying electron density. The Ni(0) ? 2IPr (IPr = N,N′-bis(2,6- diisopropylphenyl)imidazol-2-ylidene) complex associated to t-BuONa allowed N,N′-diarylation at 100 °C in 1,4-dioxane with excellent yields. Selective monoarylation of diamines could be performed in THF at 65 °C.

CoII immobilized on an aminated magnetic metal-organic framework catalyzed C-N and C-S bond forming reactions: A journey for the mild and efficient synthesis of arylamines and arylsulfides

Mohammadinezhad, Arezou,Akhlaghinia, Batool

, p. 15525 - 15538 (2019)

In this work, we report a simple and versatile method for the modification of a metal-organic framework (NH2-MIL53(Al)) in a step-wise manner. To characterize the synthesized nanostructured catalyst, a variety of spectroscopic and microscopic techniques including FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX-mapping, TGA, XPS, VSM, ICP-OES and CHN have been employed. Fe3O4@AMCA-MIL53(Al)-NH2-CoII NPs, which benefit from small nanocrystalline size (10-30 nm, according to the XRD and TEM data) in combination with the coexistence of magnetic nanoparticles, a metal-organic framework, and cobalt species, were found to be an excellent environment catalyst to promote the C-N and C-S cross coupling reactions. A wide range of functional substrates including electron-withdrawing and electron-donating aryl halides underwent the coupling reaction with aromatic/heteroaromatic/benzylic and aliphatic amines and sulfides. The results demonstrated that the yields of the target products were good to excellent and the catalyst can be recycled for at least seven recycling runs without a discernible decrease in its catalytic activity. Furthermore, the heterogeneity studies (such as hot filtration and poisoning tests) efficiently confirmed that the as-synthesized nanostructured catalyst is heterogeneous and completely stable under the reaction conditions. We hope that our study inspires more interest in designing novel catalysts based on using low-cost metal ions (such as cobalt) in the field of cross coupling reactions.

Cu(OAc)2-porphyrins as an efficient catalytic system for base-free, nature mimicking Chan–Lam coupling in water

Venkateswarlu, Katta,Rao, Kanusu Umamaheswara

, (2021/03/03)

The use of porphyrins as ligands in organic synthesis reveals the natural process, because these are the constituent motifs of catalysts in many bio-organic reactions. This article presents the synthesis of two N-pincer tetradentate porphyrins; tetrasodium meso-tetra(p-sulfonatophenyl)phorphyrin (H2TSTpSPP) and meso-tetra(m-carboxyphenyl)porphyrin (H2TmCPP), and study on their aptness for Cu-catalyzed C–N coupling reactions of arylboronic acids and amines (Chan–Lam coupling reaction) in water under external base free conditions. The porphyrins and Chan–Lam coupling products were well characterized by their spectral analysis. The high product yields, application of nature-inspired conditions, large extent of substrates, ease of making and handling the ligands, avoidance of base, and use of water as reaction media are the attractive attributes of this finding.

Substituted anilino-benzothiazole-2-thioketone compound as well as preparation method and application thereof

-

, (2020/06/05)

The invention discloses a substituted anilino-benzothiazole-2-thioketone compound and a preparation method thereof. In addition, the invention also relates to an application of the compound in rubberproducts. The substituted anilino-benzothiazole-2-thioketone compound disclosed by the invention not only can promote rubber vulcanization, but also can prolong the service life of the rubber products.

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