Aromatic Amines and Related Compounds

Arcos, J.C. and Argus, M.F. (1974) Chemical Induction of Cancer. Structural Bases and Biologic Mechanism, Vol. II B, Aromatic Amines and Related Compounds, Academic Press, New York. 

Clayson, D.B., Garner, R.C., "Carcinogenic Aromatic Amines and Related Compounds," "Chemical Carcinogens," C.E. Searle, Ed., pp. 366-A61, American Chemical Society, Washington, D.C., 1976. 

Swan. G. A., Studies of the reaction of benzoyl peroxide with N,N-disubstituted aromatic amines and related compounds. V, J. Chem. Soc. C, 2880, 1971. 

Gamer, R.C., C.N. Martin, and D.B. Clayson Carcinogenic aromatic amines and related compounds Chapter 4 in Chemical carcinogens. Second edition, edited by C.E. Searle, American Chemical Society Monograph 182, American Chemical Society, Washington, DC (1984) 175-276. 

Parris, G. E. 1980. Environmental and metabolic transformations of primary aromatic amines and related compounds. Residue Rev. 76 1-24. 

Air Monitoring. The atmosphere in work areas is monitored for worker safety. Volatile amines and related compounds can be detected at low concentrations in the air by a number of methods. Suitable methods include chemical, chromatographic, and spectroscopic techniques. For example, the NIOSH Manual of Analytical Methods has methods based on gas chromatography which are suitable for common aromatic and aHphatic amines as well as ethanolamines (67). Aromatic amines which diazotize readily can also be detected photometrically using a treated paper which changes color (68). Other methods based on infrared spectroscopy (69) and mass spectroscopy (70) have also been reported. 

Some Aromatic Amines and Related NItro Compounds—Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals 1978 400 pages... 

Bhat KL, Hayik S, Sztandera L, Bock CW. Mutagenicity of aromatic and heteroaromatic amines and related compounds A QSAR investigation. QSAR Combin Sci. 2005 24(7) 831 13. 

Some Aromatic Amines and Related Nitro Compounds - Hair dyes. Colouring Agents and Miscellaneous Industrial Chemicals, lARC Monographs on the Evaluation of Carcinogenic Risks to Humans, Volnme 16, lARC, Lyon, France, 1978, p.325. 

Exposure to amines and related compounds has large impact on human health workers exposed to benzidine and naphthylaanine have developed cancer of the bladder [12,13] the Food and Drug Administration (F.O.A.) has found that aromatic amines [14] and nitroaromatics [15] can enter the food chain. In addition, many degradation products from nitroaromatics are easily polymerized, in presence of oxygen, to persistent macromolecules [16]. The wide distribution of these compounds in the environment, coupled with their toxicity, has given rise to concern about their environmental fate. 

Amines and Related Compounds.—Recent advances in the amination of aromatic compounds have been reviewed, but certain specific syntheses of aromatic amines are worthy of mention. The literature describes attempts to prepare amines by catalytic hydrogenation of phenylhydrazones. This has suffered from difficulties arising from self-condensation of the two amines formed, but a recent report describes how this can be overcome by performing the reactions in the presence of aqueous hydrochloric acid and a suitable solvent, resulting in distribution of the hydrogenolysis products between two phases. In this way m-aminobenzylamine has been obtained from the phenylhydrazone of m-nitro-benzaldehyde in high yield. 

Aromatic Amines and Phenols. The discovery that sulfaguanidine [57-67-0] was goitrogenic to rats was serendipitous. Many related compounds were then examined, and the aniline moiety was usually present (2,6). Such compounds, as well as resorcinol-like phenols, may act as goitrogens by inhibiting thyroid peroxidases. These are not used clinically. 

One of the most general pyrrole syntheses is the cyclizative condensation of 1,4-dicarbonyl compounds with ammonia, a primary amine or related compound. The mechanistic pattern involves formation of carbinolamine and imine intermediates followed by aromatization. This method is sometimes referred to as the Paal-Knorr pyrrole synthesis (equation 65) (B-77MI30601). Once the dicarbonyl compound is available, the cyclization normally proceeds in good yield, so ease of access to the diketone is of major importance in determining the applicability of this method to specific pyrroles. Pyrrole formation usually takes place on heating the diketone in a solvent such as benzene or toluene with a catalytic amount of acid. An alternative method involves heating the dicarbonyl compound and an amine salt... 

Likewise, the luminescence properties of many analytes can be altered in the presenoe of surfactant aggregates (4,7.,8.). Consequently, addition of micelle-forming surfactants (present either in the LC mobile phase or added post-column) can improve the sensitivity of fluorimetric LC detectors (49,482). Micellar spray reagents have been utilized to enhance the fluorescence densitometric detection of dansylamino acids or polycyclic aromatic hydrocarbons (483). The effect was observed for TLC performed on cellulose or polyamide stationary phases with the micellar spray reagent being either CTAC, SB-12, or NaC (483). More recently, use of nonionic Triton X-100 has been found to improve the HPLC detection of morphine by fluorescence determination after post-column derivatization (486) as well as improve the N-chlorination procedure for the detection of amines, amides, and related compounds on thin-layer chromatograms (488). 

Aminoalkyl and Related Acids. - Further development of the classical three component approach to aminoalkylphosphonates (the Kabachnik-Fields reaction) has been reported. The reaction of aldehydes, hydroxylamines and dimethyltrimethylsilyl phosphite using lithium perchlorate/diethyl ether as a catalyst gives N-trimethylsilyloxy-a-aminophosphonate derivatives. The catalytic activities of various lanthanide triflates as well as indium trichloride have been examined for the Kabachnik-Fields type reactions of aldehydes, amines and the phosphorus nucleophiles HP(0)(0Et)2 and P(OEt)3 in ionic liquids. TaCb-Si02 has been utilized as an efficient Lewis acid catalyst for the coupling of carbonyl compounds, aromatic amines and diethyl phosphite to produce a-... 

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