Aminophenyl Ether

4-Aminophenyl Ether (4,4-Oxydianiline, 4,4-Diaminodiphenyl Oxide, N-Phenylbenzeneamine) 

Uses 4-Aminophenyl ether is a resin used in the manufacture of a variety of industrial products, (e.g., in insulating varnishes, flame-retardant fibers as wire enamels, coatings, films). It also is used in the manufacture of other industrial fire-resistant products. 

Toxicity 4-Aminophenyl ether is highly toxic to animals. It shows sufficient evidence as a carcinogen and has caused adenomas and carcinomas in the thyroid and liver of experimental rats.75,76 

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Hydrogenation of the dibenzoxadiazepine 1 in the presence of platinum results in ring opening with the formation of bis(2-aminophenyl) ether (4).325... 

The purification of chlornitrofen and the reduced metabolite, 2,4,6-trichlorophenyl 4-aminophenyl ether (CNP-NH2) in brown rice and vegetables was investigated. ... 

Biphenylamines, al30, al31 2,2 -Bipyridine, d790 Bis(2-aminoethyl)amine, d362 Bis(4-aminophenyl)ether, o67... 

The second synthesis [6], based on radical chemistry to achieve the crucial Caryi-Cgryi bond, required as the starting material the 2-bromobenzyl-2 -aminophenyl ether (11) (Scheme 2). It was secured by alkylation of o-nitrophenol with 2-bromo-4,5-methylenedioxybenzyl chloride, followed by catalytic reduction of the resulting nitropheny ether. 11 when subjected to the action of tri-n-butyltinhydride in the presence of 2,2 -azobisisobutyronitrile furnished a... 

The-Claisen rearrangement to the ortho position is a first-order reaction,67 68 and the process does not require catalysis by acids and bases. The rearrangement is intramolecular, since rearrangement of mixtures of ethers such as allyl /3-naphthyl ether and cinnamyl phenyl ether,60 or cinnamyl 4-methylphenyl ether and allyl 4-aminophenyl ether,68 yields none of the cross products which would result from an intermolecular reaction. The process is best represented by the cyclic mechanism, in which the following processes take place, with the electronic shifts during reaction indicated by the arrows.23 39 69... 

First, the nylon-salt-type monomers such as XPME [20], XTPE [21, 22], and ODPME [23] with exactly 1 1 composition were prepared from a series of aliphatic diamines (X standing for the number of methylene unit) or aromatic bis(4-aminophenyl) ether (ODA) and the corresponding aromatic tetracarbox-ylic acid half diesters (diacid-diesters) such as pyromellitic acid diethyl ester (PME) and 3,3",4,4"-p-terphenyltetracarboxylic acid diethyl ester (TPE). 

Another successful example is the solid-state thermal synthesis of the wholly aromatic polyimide P-ODPM (Tg=410 °C) by the polycondensation of the aromatic salt monomer ODPMA derived from bis(4-aminophenyl) ether and py-romellitic acid (see Eq. 3, R =H). Figure 3 shows the DSC and TG curves of salt monomer ODPMA [27]. 

SYNS p-AMINOPHENYL ETHER 4-AMINOPHENYL ETHER BIS(p-AMINOPHENYL)ETHER BIS(4-AMINOPHENYL)ETHER DADPE 4,4 -DIAMINO-BIPHENYLOXIDE DIAMINODIPHENYL ETHER p,p -DIAMINODIPHENYL ETHER 4,4-DIAMINODI-PHENYL ETHER 4,4 -DIAMINODIPHENYL OXIDE 4,4 -DIAMINOPHENYL ETHER NCI-C50146 OXYBIS(4-AMINOBENZENE) p,p -OXYBIS(ANILINE)... 

AMINO-2-PHENYLETHANE see PDE250 4-AMINOPHENYL ETHER see OPMOOO p-AMINOPHENYL ETHER see OPMOOO... 

BIS(2-AMINOPHENYL)DISULFIDE see DXJ800 BIS(o-AMINOPHENYL)DISULFIDE see DXJ800 l,l -BIS(2-AMINOPHENYL)DISULFIDE see DXJ800 BIS(4-AMINOPHENYL)ETHER see OPMOOO BIS(p-AMINOPHENYL)ETHER see OPMOOO BIS(4-AMINOPHENYL)METHANE see MJQOOO BIS(p-AMINOPHENYL)METHANE see MJQOOO 2, 4-BIS(AMINOPHENYL)METHANE see MJP750 BIS(4-AMINOPHENYL) SULFIDE see TFIOOO BIS(p-AMINOPHENYL)SULFIDE see TFIOOO BIS(4-AMINOPHENYL) SULFONE see SOA500... 

Polyimide. A typical polyimide results from the condensation of pyromellitic dianhydride and bis-4(aminophenyl)ether. The final insoluble polydiimide is obtained by dehydration of a soluble polyamic acid, namely,... 

Beilstein Handbook Reference) AI3-18375 Aniline, 4,4 -oxydi- Benzenamine, 4,4 -oxybis- Bis(4-aminophenyl) ether Bis(p-aminophenyl) ether BRN 0475735 CCRIS 491 Dadpe Di-(4-aminophenyl)ether Diaminodiphenyl ether EINECS 202-977-0 Ether, 4,4 -diaminodiphenyl HSDB 1316 NCI-C50146 NSC 37075 p,p -Oxydianiline. Crystals mp = 189°. 

The following amines, inter alia, have been prepared by use of nickel and hydrazine hydrate 58 /7-aminophenyl phenyl ether, 4-aminocinnamic acid, 3-aminobenzophenone, and bis-p-(aminophenyl) ether. Palladium and hydrazine hydrate were used successfully in reduction of 2-nitrofluorene.59... 

However, the opposite effects are also known, as for example, in blends of polyethersulfone (PES) with polyaramid (PARA) prepared by polycondensation of bis (4-aminophenyl)ether with isopthaloyl chloride [Nakata et al, 1990]. The PARA had been thought to be an amorphous polymer, whereas it did crystallize in the blend. The results suggest that the crystallization of PARA was induced by the presence of PES, i.e., this is an example of the blend-induced crystallization. The aramid seems to be a dormant crystalline polymer. In other words, the crystallizability is latent but crystallization in neat PARA was not possible even when annealing - it did take place in the presence of PES. This may be due to an increase of chain mobility by decreasing the glass transition temperature (T ) on blending PARA with PES that has lower T. ... 

Incorporating aromatic silane functions into aromatic polyamides can also improve solubility [45], and was shown recently by Vernekar et al. [38] with polymers 23. These polyamides from 3,3 or 4,4 [suIfonylbis-(4,l-phenyleneoxy)] bisbenzenamine have higher solubility than those from bis(4-aminophenyl)ether. They are soluble in amide solvents, pyridine and w-cresol, and some in THF and nitrobenzene. They also have a high Tj in the range of 477-513 °C, and a Tg in the range of 209-246 °C. 

Song et al. [46] have used a carboxyl-functionalized ionic liquid as soluble support to synthesize a small library of 4-aminophenyl ethers via Williamson reaction and extracting with ethyl acetate in good yields (75-80%) and purities (99%). The recovered ionic liquid support was reused several times with consistent loading capacity (Scheme 5.5-30). 

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