Aminodiphenyl

Physical Form. Colorless, crystalline compound darkens on oxidation 

Previously used as a rubber antioxidant no longer produced on a commercial scale 

Toxicology. 4-Aminodiphenyl exposure is associated with a high incidence of bladder cancer in humans. 

Of 171 workers exposed to 4-amin-odiphenyl for 1.5-19 years, 11% had bladder tumors the tumors appeared 5-19 years after initial exposure.  

In a smdy of 503 exposed workers, there were 35 histologically confirmed bladder carcinomas and an additional 24 men with positive cytology.  

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Solution I Dissolve 1 g 2-aminodiphenyl (biphenyl-2-ylamine) in 100 ml ethanol. 

Spray solution For sugars [3] dissolve 3 g 2-aminodiphenyl in 100 ml glacial acetic acid and add 1.5 ml 85% orthophosphoric acid. 

Aminodiphenyl reacts with carbonyl compounds to form colored or fluorescent Schiff s bases with the elimination of water ... 

Amino-2, 5-dichlorobenzophenone (ADB) 226,227 4-Amino-2,3-dimethyl-l-phenyl-3-pyrazolin-5-one 158 2-Aminodiphenyl reagent 157,158 Aminoglycoside antibiotics 107, 270, 284, 354, 380, 423, 434... 

In addn to the above p-isomer, called by FishbeinfRef 4) Diazo-4-aminodiphenyl Perchlorate, there was prepd the o-isomer, called Diazo-2-aminodiphenyl Perchlorate. This isomer also proved to be expl... 

The nitro group can take part in the formation of heterocyclic nitrogen-containing rings. For example, one of the well known methods for the preparation of phenazine derivatives consists in heating derivatives of 2-nitro-2 -aminodiphenyl-arnine at high temperature (Kehrmann et al. [11]) ... 

Other functional groups may be present during reduction. Aromatic amino ethers are prepared by the same general procedures described above, e.g., 772-aminoanisole (80%) and 2-aminodiphenyl ether (94%). The reduction of o-nitrobenzaldehyde to the sensitive o-aminobenzaldehyde is successfully accomplished by the action of ferrous sulfate and ammonia (75%). m-Dimethylaminobenzaldehyde is formed by reduction of the nitro acetal in aqueous solution with sodium sulfide followed by methyla-tion (74% over-all) or by catalytic reduction of m-nitrobenzaldehyde in... 

To a warm solution (50 °C) of the 2-aminodiphenyl ketone oxime (70 g, 0.33 mol) in glacial HOAc (420 mL) was added chloroacetyl chloride (74.6 g, 0.66 mol). The mixture was left at rt for 48 h, saturated with anhyd HCl (g), and concentrated in vacuo. The residue was dissolved in CHjClj and washed with ice-cold NajCO soln. The organic solution was dried, concentrated to a small volume, and diluted with petroleum ether. The precipitated crystals were filtered. The mother liquid yielded an additional crop. After recrystallization, the product formed as yellow needles yield 67.8 g (76%) mp 160-161 °C. 

Oxidative preparations have a wide scope, are applied to readily accessible starting materials (which can be prepared in situ), and afford products in good yields. 2-Aminodiphenyl-amines are smoothly converted into phenazines by oxidation. Thus, the 2-aminodiphenylamine derivative 20 undergoes intramolecular cyclization to compound 21 (mp 129 C). See also Houben-Weyl, Vol. 4/1 b, pp 174, 978 and 979. 

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