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1,4-Bis(diphenylamino)benzene, also known as N,N,N',N'-tetraphenyl-p-phenylenediamine (TPPD), is a triarylamine derivative with notable electrochemical and photochemical properties. It serves as a precursor for synthesizing polytriphenylamine derivatives like PDDP, which exhibit high free radical density and are explored as organic cathode materials for lithium-ion batteries. Additionally, TPPD forms a stable cation radical (TPPD.+) that participates in photoinduced electron-transfer reactions, acting as a photocatalyst in the oxidation of alcohols to aldehydes or ethers. These characteristics highlight its utility in organic electronics and redox-active systems.

14118-16-2

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14118-16-2 Usage

Check Digit Verification of cas no

The CAS Registry Mumber 14118-16-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,1,1 and 8 respectively; the second part has 2 digits, 1 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 14118-16:
(7*1)+(6*4)+(5*1)+(4*1)+(3*8)+(2*1)+(1*6)=72
72 % 10 = 2
So 14118-16-2 is a valid CAS Registry Number.
InChI:InChI=1/C30H24N2/c1-5-13-25(14-6-1)31(26-15-7-2-8-16-26)29-21-23-30(24-22-29)32(27-17-9-3-10-18-27)28-19-11-4-12-20-28/h1-24H

14118-16-2SDS

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 1-N,1-N,4-N,4-N-tetraphenylbenzene-1,4-diamine

1.2 Other means of identification

Product number -
Other names n,n,n',n'-tetraphenylbenzene-1,4-diamine

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:14118-16-2 SDS

14118-16-2Relevant academic research and scientific papers

Arylation of diarylamines catalyzed by Ni(II)-PPh3 system

Chen, Chen,Yang, Lian-Ming

, p. 2209 - 2211 (2005)

(Chemical Equation Presented) The cross-coupling of bromomagnesium diarylamides, generated in situ from diarylamines, with aryl bromides or iodides can be effected with a simple NiCl2(PPh3) 2-PPh3 catalyst system under relatively mild conditions. This coupling reaction is an inexpensive, convenient, and practical method, functioning as an alternative to the corresponding Pd-catalyzed or Cu-mediated process for the synthesis of triarylamines.

Polytriphenylamine derivative with high free radical density as the novel organic cathode for lithium ion batteries

Su, Chang,Yang, Fang,Ji, Lvlv,Xu, Lihuan,Zhang, Cheng

, p. 20083 - 20088 (2014)

Polytriphenylamine derivative, poly[N,N,N,N-tetraphenylphenylenediamine] (PDDP), with a high free radical density, has been synthesized and studied as a cathode material for organic free radical batteries for the first time. The chemical structure, morpho

Photochemistry of Cation Radicals in Solution: Photoinduced Electron-transfer Reactions between Alcohols and the N,N,N',N'-Tetraphenyl-p-phenylenediamine Cation Radical

Moutet, Jean-Claude,Reverdy, Gilbert

, p. 654 - 655 (1982)

Irradiation of the N,N,N',N'-tetraphenyl-p-phenylenediamine cation radical (TPPD.+) with benzyl alcohol causes its reduction to TPPD and oxidation of the alcohol into benzaldehyde; with benzhydrol and 1-phenylethanol the corresponding symmetrical ethers are formed in a photocatalytic process in which TPPD.+ is recycled via two successive electron transfers.

SOLVENT-FREE CROSS-COUPLING REACTION, AND PRODUCTION METHOD USING SAID REACTION

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Paragraph 0311-0314; 0322, (2021/12/30)

Disclosed is a cross-coupling reaction method which forms a chemical bond selected from C—N, C—B, C—C, C—O and C—S bonds, the method comprising: preparing an aromatic compound (1) having a leaving group;preparing a compound (2) capable of undergoing a cross-coupling reaction selected from an aromatic amino compound (2-1), a diboronic acid ester or the like (2-2), an aromatic boronic acid or the like (2-3), an aromatic compound (2-4) having a hydroxyl group and an aromatic compound (2-5) having a thiol group; andperforming a cross-coupling reaction of the compound (1) with the compound (2) in the presence of a palladium catalyst, a base and a compound (4) having a carbon-carbon double bond or a carbon-carbon triple bond, in the absence of a solvent.

Electron-Catalyzed Coupling of Magnesium Amides with Aryl Iodides

Kiriyama, Kazuya,Okura, Keisho,Tamakuni, Fumiko,Shirakawa, Eiji

supporting information, p. 4519 - 4522 (2018/03/13)

An electron was found to catalyze the coupling of magnesium diarylamides with aryl iodides giving triarylamines through a radical-anion intermediate. The transformation requires no transition metal catalysts or additives, and a wide array of products are formed in good-to-excellent yields.

Triphenylamine structure-containing compound, and preparation method and application thereof

-

Paragraph 0050; 0051-0052, (2017/12/27)

The invention provides a triphenylamine structure-containing compound, and a preparation method and an application thereof, and belongs to the technical field of organic photoelectric materials. The compound has a structure represented by formula (I). Org

Synthesizing method of tetracarboxylic acid N,N,N',N'-tetra-(4'-carboxyl biphenyl)-1,4-phenylenediamine

-

Paragraph 0015; 0018; 0019, (2018/01/03)

The invention relates to a synthesizing method of tetracarboxylic acid N,N,N',N'-tetra-(4'-carboxyl biphenyl)-1,4-phenylenediamine. The synthesizing method comprises the following steps of enabling 1,4-benzene dibromide and diphenylamine to generate N,N,N',N'-tetraphenyl-1,4-phenylenediamine (A) through arylamination reaction; enabling the N,N,N',N'-tetraphenyl-1,4-phenylenediamine (A) and NBS (N-bromosuccinimide) to generate N,N,N',N'-tetra-(4-bromophenylacetone)-1,4-phenylenediamine (B); enabling the N,N,N',N'-tetra-(4-bromophenylacetone)-1,4-phenylenediamine (B) and 4-methyl boronobenzoate to generate N,N,N',N'-tetra-(4'-methoxycarbonyl biphenyl)-1,4-phenylenediamine (C); hydrolyzing the N,N,N',N'-tetra-(4'-methoxycarbonyl biphenyl)-1,4-phenylenediamine (C), so as to generate a target compound D, namely N,N,N',N'-tetra-(4'-carboxyl biphenyl)-1,4-phenylenediamine. The synthesizing method has the advantages that the poly-benzene ring aromatic tetracarboxylic acid compound not reported in literature is synthesized; the synthesizing method is simple, the cost is low, the yield rate is high, and the purity is high. The target compound is shown as a formula shown in the attached figure.

Quaternary carboxylic acid N, N, N', four N' - (4 - carboxyl vinyl phenyl) - 1, 4 - phenylenediamine synthetic method (by machine translation)

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Paragraph 0019; 0020, (2018/03/01)

The invention of a four-membered carboxylic acidN,N,N',N' - Four (4 - carboxyl vinyl phenyl) - 1, 4 - phenylenediamine synthetic method, 1, 4 - bromobenzene with two passes the amination reaction of the diphenylamineN,N,N',N' - Tetraphenyl - 1, 4 - phenyl

Chemoselective amination of bromoiodobenzenes with diarylamines by palladium/Xantphos or ligand-free copper catalysts

Kanazawa, Yoshinori,Yokota, Tomo,Ogasa, Hiroshi,Watanabe, Hirotaka,Hanakawa, Taisyun,Soga, Shinichi,Kawatsura, Motoi

, p. 1395 - 1402 (2015/02/19)

We report the chemoselective amination of bromoiodobenzenes with diarylamines by palladium/Xantphos or a ligand-free copper catalyst. The reactions by these two types of catalysts proceeded with a high chemoselectivity and afforded monobrominated triarylamines in good yields. These products are useful intermediates for the synthesis of unsymmetrical bistriarylamines.

Catalytic carbon-nitrogen bond-forming cross-coupling using N-trimethylsilylamines

Minami, Yasunori,Komiyama, Takeshi,Shimizu, Kenta,Hiyama, Tamejiro,Goto, Osamu,Ikehira, Hideyuki

, p. 1437 - 1446 (2015/11/16)

Carbon-nitrogen bond-forming cross-coupling reaction of haloarenes with N-trimethylsilyl (TMS)-substituted secondary and primary arylamines proceeded with the aid of a palladium catalyst and a fluoride activator. Various TMS-N(aryl)2, TMS-NH(aryl), and TMS-N(alkyl)2 reacted to give the corresponding coupled products in high yields. Multi-TMS-amine nucleophiles such as N,N-(TMS)2-aniline and N,N′-Ph2-N,N′-(TMS)2-p-phenylenediamine also participated in this C-N coupling to give multiply C-N coupled products in high yields. The novel C-N cross-coupling reaction was successfully applied to C-N bond-forming polymerization. Relative rates of the cross-coupling of p-bromotoluene with N-TMS-substituted primary and secondary amines showed that N-TMS-diphenylamine reacted faster than N-TMS-N-methylaniline or N-TMS-aniline, and N-TMS-morpholine was the least reactive, indicating that the low basicity of the nitrogen nucleophile is the key for the smooth coupling.

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