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2-Aminodiphenylamine, also known as N-Phenyl-o-phenylenediamine, is an organic compound that exists in the form of a white to light yellow or light red powder or crystal. It is widely recognized for its role as an intermediate in the synthesis of various organic compounds and pharmaceuticals, making it a valuable component in the chemical and pharmaceutical industries.

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  • 534-85-0 Structure
  • Basic information

    1. Product Name: 2-Aminodiphenylamine
    2. Synonyms: LABOTEST-BB LT00080731;2-AMINODIPHENYLAMINE;TIMTEC-BB SBB000244;N-(2-AMINOPHENYL)-N-PHENYLAMINE;N-PHENYL-1,2-PHENYLENEDIAMINE;N-PHENYL-O-PHENYLENEDIAMINE;O-AMINODIPHENYLAMINE;C.I. 50005
    3. CAS NO:534-85-0
    4. Molecular Formula: C12H12N2
    5. Molecular Weight: 184.24
    6. EINECS: 208-606-9
    7. Product Categories: Anilines, Aromatic Amines and Nitro Compounds;API intermediates;Nitrogen Compounds;Building Blocks;Chemical Synthesis;Organic Building Blocks;Polyamines
    8. Mol File: 534-85-0.mol
    9. Article Data: 57
  • Chemical Properties

    1. Melting Point: 77-80 °C(lit.)
    2. Boiling Point: 108 °C / 0.4mmHg
    3. Flash Point: 181.6 °C
    4. Appearance: Pink-violet or gray-brown/Crystalline Powder
    5. Density: 1.1160 (rough estimate)
    6. Vapor Pressure: 0.000143mmHg at 25°C
    7. Refractive Index: 1.6266 (estimate)
    8. Storage Temp.: 2-8°C
    9. Solubility: N/A
    10. PKA: 4.45±0.10(Predicted)
    11. Water Solubility: Soluble in acetone, chloroform and benzene. Insoluble in water.
    12. BRN: 908984
    13. CAS DataBase Reference: 2-Aminodiphenylamine(CAS DataBase Reference)
    14. NIST Chemistry Reference: 2-Aminodiphenylamine(534-85-0)
    15. EPA Substance Registry System: 2-Aminodiphenylamine(534-85-0)
  • Safety Data

    1. Hazard Codes: Xn,Xi
    2. Statements: 20/22-38-36/37/38
    3. Safety Statements: 22-24-28A-26
    4. RIDADR: 2811
    5. WGK Germany: 3
    6. RTECS:
    7. F: 8
    8. TSCA: Yes
    9. HazardClass: 6.1(b)
    10. PackingGroup: III
    11. Hazardous Substances Data: 534-85-0(Hazardous Substances Data)

534-85-0 Usage

Uses

Used in Organic Synthesis:
2-Aminodiphenylamine is used as an intermediate in the organic synthesis industry for the production of a range of compounds. Its unique chemical structure allows it to participate in various reactions, facilitating the creation of diverse organic molecules.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-Aminodiphenylamine is utilized as an intermediate for the synthesis of different drugs. Its presence in the manufacturing process contributes to the development of various medications, highlighting its importance in the healthcare sector.
Used in Chemical Industry:
2-Aminodiphenylamine is also employed in the chemical industry for the production of a variety of chemical products. Its versatility and reactivity make it a valuable asset in the synthesis of numerous compounds, further expanding its applications across various industries.

Synthesis

The synthesis of 2-Aminodiphenylamine is as folliows:Reaction flask was added 0.108 g of o-phenylenediamine (1 mmol), phenylhydrazine0.216 g (2 mmol), CuPc 0.058 Ke (0.1 mmol), Cu (OAc) 2 0.02 g (0.1 mmol) and 10 ml ofacetonitrile, 15 °C reaction; TLC until the reaction was followed completely finished;the crude product after the reaction was subjected to column chromatography (petroleumether: ethyl acetate = 100: 1) to give the desired product (71% yield).

storage

Keep container tightly closed. Store in cool, dry conditions in well sealed containers. It is sensitive to light. Store at room temperature. Incompatible with acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents.

Purification Methods

Crystallise the amine from H2O. [Beilstein 13 IV 43.]

Check Digit Verification of cas no

The CAS Registry Mumber 534-85-0 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 4 respectively; the second part has 2 digits, 8 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 534-85:
(5*5)+(4*3)+(3*4)+(2*8)+(1*5)=70
70 % 10 = 0
So 534-85-0 is a valid CAS Registry Number.
InChI:InChI=1/C12H12N2/c13-11-8-4-5-9-12(11)14-10-6-2-1-3-7-10/h1-9,14H,13H2

534-85-0 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
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  • Detail
  • Alfa Aesar

  • (L11616)  N-Phenyl-o-phenylenediamine, 98%   

  • 534-85-0

  • 5g

  • 244.0CNY

  • Detail
  • Alfa Aesar

  • (L11616)  N-Phenyl-o-phenylenediamine, 98%   

  • 534-85-0

  • 25g

  • 944.0CNY

  • Detail
  • Sigma-Aldrich

  • (07900)  N-Phenyl-o-phenylenediamine  purum, ≥98.0% (NT)

  • 534-85-0

  • 07900-25G

  • 1,230.84CNY

  • Detail
  • Aldrich

  • (P28352)  N-Phenyl-o-phenylenediamine  98%

  • 534-85-0

  • P28352-10G

  • 627.12CNY

  • Detail

534-85-0SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 2-Aminodiphenylamine

1.2 Other means of identification

Product number -
Other names mono-N-phenyl-o-phenylenediamine

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
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:534-85-0 SDS

534-85-0Relevant articles and documents

N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis

Perin,Hok,Be?,Persoons,Vanstreels,Daelemans,Vianello,Hranjec

, (2020/12/02)

We present the design, synthesis and biological activity of novel N-substituted benzimidazole based acrylonitriles as potential tubulin polymerization inhibitors. Their synthesis was achieved using classical linear organic and microwave assisted techniques, starting from aromatic aldehydes and N-substituted-2-cyanomethylbenzimidazoles. All newly prepared compounds were tested for their antiproliferative activity in vitro on eight human cancer cell lines and one reference non-cancerous assay. N,N-dimethylamino substituted acrylonitriles 30 and 41, bearing N-isobutyl and cyano substituents placed on the benzimidazole nuclei, showed strong and selective antiproliferative activity in the submicromolar range of inhibitory concentrations (IC50 0.2–0.6 μM), while being significantly less toxic than reference systems docetaxel and staurosporine, thus promoting them as lead compounds. Mechanism of action studies demonstrated that two most active compounds inhibited tubulin polymerization. Computational analysis confirmed the suitability of the employed benzimidazole-acrylonitrile skeleton for the binding within the colchicine binding site in tubulin, thus rationalizing the observed antitumor activities, and demonstrated that E-isomers are active substances. It also provided structural determinants affecting both the binding position and the matching affinities, identifying the attached NMe2 group as the most dominant in promoting the binding, which allows ligands to optimize favourable cation???π and hydrogen bonding interactions with Lys352.

Design, synthesis, and biological evaluation of benzo[d]imidazole-2-carboxamides as new anti-TB agents

Dhameliya, Tejas M.,Patel, Kshitij I.,Tiwari, Rishu,Vagolu, Siva Krishna,Panda, Dulal,Sriram, Dharmarajan,Chakraborti, Asit K.

, (2020/12/29)

Tuberculosis is the leading cause of death globally among infectious diseases. Due to the development of resistance of Mycobacterium tuberculosis to currently used anti-TB medicines and the TB-HIV synergism the urgent need to develop novel anti-mycobacterial agents has been realized. The drug-to-target path has been the successful strategy for new anti-TB drug development. All the six drug candidates that have shown promise during the clinical trials and some of these being approved for treatment against MDR TB are the results of phenotype screening of small molecule compound libraries. In search of compounds belonging to novel pharmacophoric class that could be subjected to whole cell assay to generate new anti-TB leads the benzo[d]imidazole-2-carboxamide moiety has been designed as a novel anti-TB scaffold. The design was based on the identification of the benzimidazole ring as a prominent substructure of the FDA approved drugs, the structural analysis of reported anti-TB benzimidazoles, and the presence of the C-2 carboxamido functionality in novel bioisoteric anti-TB benzothiazoles. Twenty seven final compounds have been prepared via NH4Cl-catalyzed amidation of ethyl benzo[d]imidazole-2-carboxylates, as the required intermediates, obtained through a green “all water” one-pot synthetic route following a tandem N-arylation-reduction-cyclocondensation procedure. All of the synthesised target compounds were assessed for anti-TB potential using H37Rv ATCC27294 strain. Thirteen compounds were found with better MIC (0.78–6.25 μg/mL) than the standard drugs and being non-cytotoxic nature ( 60) and a few others e.g., 8a, 8f, 8k and 8o are the next best anti-TB hits (MIC: 1.56 μg/mL). The determination and analysis of various physiochemical parameters revealed favorable druglike properties of the active compounds. The compounds 8a-l and 8o, with MIC values of ≤ 6.25 μg/mL, have high LipE values (10.66–11.77) that are higher than that of the suggested value of > 6 derived from empirical evidence for quality drug candidates and highlight their therapeutic potential. The highest LipE value of 11.77 of the best active compound 8e with the MIC of 0.78 μg/mL indicates its better absorption and clearance as a probable clinical candidate for anti-TB drug discovery. These findings highlight the discovery of benzimidazole-2-carboxamides for further development as new anti-TB agents.

Biomimetic alloxan-catalyzed intramolecular redox reaction with O2: One-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles

Zhang, Shiqi,Yi, Dong,Li, Guangxun,Li, Ling,Zhao, Gang,Tang, Zhuo

supporting information, (2020/12/25)

Given the necessity of sacrificial reductants in various biomimetic aerobic oxygenations, alloxan-catalyzed aerobic redox system for one-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles was developed by ingeniously binding both the substrate sulfide and sacrificial reductant. This mild and transition-metal-free protocol undergoes two oxidations without additional sacrificial reagents, except for the environmentally benign molecular oxygen.

Novel 4-phenoxy pyridine derivative and application thereof

-

Paragraph 0049; 0066-0068, (2021/06/02)

The invention relates to a novel 4-phenoxy pyridine derivative and application thereof. The 4-phenoxy pyridine derivative has a structure as shown in a general formula (I), and the pharmacological activity test result of the novel 4-phenoxy pyridine derivative shows that the 4-phenoxy pyridine derivative has a remarkable inhibition effect on human gastric cancer cells MKN45, human lung cancer cells A549, human lung cancer cells H460 and human colon cancer cells HT-29; and meanwhile, the invention relates to a strong c-Met kinase inhibition effect of the compounds, and also relates to application of the compounds and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of drugs for treating and/or preventing diseases caused by abnormal high expression of c-Met kinase, and application of the compounds and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of drugs for treating and/or preventing diseases caused by abnormal high expression of c-Met kinase. particularly relates to application in preparation of medicines for treating and/or preventing cancers.

Fe-MIL-101 modified by isatin-Schiff-base-Co: a heterogeneous catalyst for C-C, C-O, C-N, and C-P cross coupling reactions

Farrokhi, Alireza,Rouzifar, Majid,Sansano, José Miguel,Sobhani, Sara

, p. 19963 - 19976 (2021/11/12)

A metal-organic framework functionalized with a cobalt-complex is preparedviapost-synthetic modification of Fe-MIL-101-NH2. Initially, Fe-MIL-101-NH2reacted with isatin to produce Fe-MIL-101-isatin-Schiff-base, which can anchor the cobalt by the addition of cobalt acetate. The resulting MOF-Co catalyst is characterized by employing multiple techniques. This new modified MOF acts as a heterogeneous and recyclable catalyst for efficient Ullmann, Buchwald-Hartwig, Hirao, Hiyama and Mizoroki-Heck cross-coupling reactions of several aryl halides/phenylboronic acid/phenyltosylate with phenols, anilines/heterocyclic amines, triethyl phosphite, triethoxyphenylsilane and alkenes and generates the expected coupling products in good to high yields.

Chitosan nanoparticles functionalized poly-2-hydroxyaniline supported CuO nanoparticles: An efficient heterogeneous and recyclable nanocatalyst for N-arylation of amines with phenylboronic acid at ambient temperature

Seyedi, Neda,Zahedifar, Mahboobeh

, (2021/07/25)

The present study aims to prepare an effective and eco-friendly nanocatalyst for the Chan–Lam coupling reaction of phenylboronic acid and amine in aerobic conditions. For this purpose, chitosan was extracted from shrimp shells waste by demineralization, deproteinization, and deacetylation processes and then converted to chitosan nanoparticles (CSN) by the ionic gelation with tripolyphosphate anions. Afterward, poly-2-hydroxyaniline (P2-HA) was grafted to chitosan nanoparticles (NPs) to employ as the support for CuO NPs. Characterization of the nanocatalyst was done using Fourier transform infrared (FT-IR), X-ray powder diffraction (XRD), scanning electron microscopy (SEM), mapping, energy-dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM), and thermogravimetric analysis (TGA). The CuO NPs were identified in the spherical shape with an average size of 17 nm. The prepared nanocatalyst exhibited excellent catalytic performance with a high turnover number (TON) and turnover frequency (TOF) for the Chan–Lam coupling reaction of phenyl boronic acid and amines with different electronic properties. The prepared catalyst could be readily recovered and reused for at least five runs without any noticeable change in structure and catalytic performance. Chitosan (CS) was prepared via demineralization, deproteinization, and deacetylation of shrimp shell and chitosan nanoparticles (CSN) were prepared via ionic gelation process. Polymerization of 2-HA on the CSN surface was done to increase functional groups and create active sites for CuO NPs attachments. CuO NPs-P2-HA-CSN nanocomposite has been shown high efficiently for the Chan–Lam coupling reaction.

COMPOUND FOR ORGANIC OPTOELECTRONIC DEVICE, COMPOSITION FOR ORGANIC OPTOELECTRONIC DEVICE, ORGANIC OPTOELECTRONIC DEVICE AND DISPLAY DEVICE

-

Paragraph 0399-0403, (2021/11/09)

The compound according to claim 1, wherein the compound is represented by the following Formula. The present invention relates to a composition for an organic optoelectric device, an organic optoelectric device, and a display device. The details of Formula 1 are as defined in the specification.

A green and practical reduction of N-(4-chlorophenyl)-2-nitroaniline and its derivatives to corresponding N-substituted-benzene-1,2-diamines using thiourea dioxide

Cui, Jian-Lan,Wang, Ning,Wang, Xiao,Yu, Si-Yuan,Zhong, Cong-Shan

supporting information, (2020/01/22)

A new effective approach for synthesizing diverse N-substituted-benzene-1,2-diamines is reported. The treatment of N-substituted-2-nitroanilines with thiourea dioxide in the presence of sodium hydroxide efficiently formed the corresponding N-substituted-benzene-1,2-diamines, including N-(4-chlorophenyl)benzene-1,2-diamine with a good yield of 94%. The by-product is environmentally-friendly urea and is easy to separate from the product by filtration procedure that enhances the convenience of the approach.

Exploration of Fragment Binding Poses Leading to Efficient Discovery of Highly Potent and Orally Effective Inhibitors of FABP4 for Anti-inflammation

Su, Haixia,Zou, Yi,Chen, Guofeng,Dou, Huixia,Xie, Hang,Yuan, Xiaojing,Zhang, Xianglei,Zhang, Naixia,Li, Minjun,Xu, Yechun

, p. 4090 - 4106 (2020/05/20)

Fatty-acid binding protein 4 (FABP4) is a promising therapeutic target for immunometabolic diseases, while its potential for systemic inflammatory response syndrome treatment has not been explored. Here, a series of 2-(phenylamino)benzoic acids as novel and potent FABP4 inhibitors are rationally designed based on an interesting fragment that adopts multiple binding poses within FABP4. A fusion of these binding poses leads to the design of compound 3 with an ?460-fold improvement in binding affinity compared to the initial fragment. A subsequent structure-aided optimization upon 3 results in a promising lead (17) with the highest binding affinity among all the inhibitors, exerting a significant anti-inflammatory effect in cells and effectively attenuating a systemic inflammatory damage in mice. Our work therefore presents a good example of lead compound discovery derived from the multiple binding poses of a fragment and provides a candidate for development of drugs against inflammation-related diseases.

4 -phenoxypyridine compound containing quinoxalinone and application thereof (by machine translation)

-

Paragraph 0055; 0069-0071, (2020/07/13)

The invention belongs to the field of medicines, and particularly relates to 4 -phenoxypyridine compounds containing quinoxalinone and application thereof. The 4 -phenoxypyridine compound containing quinoxalinone has the structure of the general formula (I). The invention also relates to the application of the compound of the general formula (I) to inhibit c-Met kinase and provide 4 -phenoxypyridine compounds containing quinoxalinone and pharmaceutically acceptable salts thereof in preparation of medicines for treating and/or preventing diseases caused by abnormal high expression c-Met kinase. (by machine translation)

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