J?-aminophenol

Hydroquinone and A -methyl-/j-aminophenol (Metol) form a superadditive mixture which was shown by Tausch and Levenson [47] to involve the consumption primarily of hydroquinone with the preservation of Metol. This led to the regeneration theory proposed by Levenson, that Metol was acting as the developing agent at the silver halide surface and that oxidized Metol was reduced back to Metol by hydroquinone as outlined in Eqs. (30)-(33). 

It is necessary to dilute the sulphuric acid slightly or to keep the temperature low, otherwise sulphonation occurs and a j -aminophenol sulphonic acid results. Elbs was the first to prove that a considerable quantity of aniline is formed at the same time, and that a lead cathode increases the amount of this substance. 

Elemental bromine that has been produced during oxidative decomposition of organic compounds by chromic-sulfuric acid, can be detected directly and in minimal amounts through reaction with -aminophenol. A blue water-soluble product results. The basis of the color reaction is that the initial oxidation product is -quinone imine which reacts with unaltered aminophenol to form an indamine. (See detection of j -aminophenol, Vol II page 517). 

Ungar, Damgaard and Weinstein - have shown that certain well recognized anti-inflammatory drugs, salicylic acid, phenazone, amidopyrine, cinchophen and also j -aminophenol inhibit fibrinolysin (plasmin) in concentrations close to those which show anti-inflammatory activity in vivo. Salicylate may inhibit kinin formation by this indirect mechanism involving plasmin. The failure of some workers to observe any inhibition of kallikrein by salicylate in vitro does not conflict with this. 

Aminophenol [95-55-6] M 109.1, m 175-176 , pKj 4.65, pKj 9.75. Purified by soln in hot water, decolorised with activated charcoal, filtered and cooled to induce crystn. Maintain an atmosphere of N2 over the hot phenol soln to prevent its oxidation [Charles and Preiser J Am Chem Soc 74 1385 7952]. Can also be crystd from EtOH. 

Aminophenol hydrochloride [51-78-5] M 145.6, m 306 (dec). Purified by treating an aqueous soln with saturated Na2S203 filtering under an inert atmosphere, then recrystd from 50% EtOH twice and once from absolute EtOH [Livingston and Ke J Am Chem Soc 72 909 7950]. 

Lendenmann U, JC Spain (1996) 2-aminophenol 1,6-dioxygenase a novel aromatic ring cleavage enzyme purified from Pseudomonas pseudoalcaligenes JS 45. J Bacteriol 178 6227-6232. 

Wu J-F, C-W Sun, C-Y Jiang, Z-P Liu, S-J Liu (2005) A novel 2-aminophenol 1,6-dioxygenase involved in the degradation of p-chloronitrobenzene by Comamonas strain CNB-1 purification, properties, genetic cloning and expression in Escherichia coli. Arch Microbiol 183 1-8. 

Snznki H, Y Fnrnsho, T Higashi, Y Ohnishi, S Horinonchi (2006a) A novel o-aminophenol oxidase responsible for formation of the phenoxazinone chromophore of grixazone. J Biol Chem 281 824-833. 

Takenaka S, S Mnrakami, R Shinke, K Hatakeyama, H Ynknwa, K Aoki (1997) Novel genes encoding 2-aminophenol 1,6-dioxygenase from Pseudomonas species AP-3 growing on 2-aminophenol and catalytic properties of the pnrified enzyme. J Biol Chem 212 14727-14732. 

Goebel, W.F., Babers, F.H., and Avery, O.T. (1932) Chemo-immunological studies on conjugated carbohydrate-proteins VI. The synthesis of p-aminophenol alpha-glucoside and its coupling with protein. J. Exp. Med. 55(5), 761-767. 

Z. Zhang, H. Liu, and J. Deng, A glucose biosensor based on immobilization of glucose oxidase in electropolymerized o-aminophenol film on platinized glassy carbon electrode. Anal. Chem. 68, 1632-1638 (1996). 

C.-E. Lin, Y.-T. Chen and T.-Z. Wang, Separation of benzenediamines, benzenediols and aminophenols in oxidative hair dyes by micellar electrokinetic chromatography using cationic surfactants. J. Chromatogr.A, 837 (1999) 241-252. 

Elder RL Final report on the safety assessment of p-aminophenol, w -aminophenol and o-aminophenol. J Am Coll Toxicol 7(3) 279-333, 1988... 

Spengler, J., Osterburg, I. Korte, R. (1986) Teratogenic evaluation of -toluenediamine sulfate resorcinol and/ -aminophenol in rats and rabbits (abstract). Teratology, 33, 31A... 

For example, the molecular formula for 4-aminophenol (1,1) is C(iH7NO. The formula of the fully saturated, acyclic parent structure [C H 2,j+2+vNvO ., where H is the total number of hydrogens and halogens] would therefore be C6H(i2+2+i)NO, i.e. C6H15NO. The difference in the number of hydrogens is therefore 15-7 = 8, so there are 4 DBEs. 

In an early publication, Zelentsov reported the preparation of a complex with subnormal magnetic properties 44 = 0.87 BM) with the SB (101).777 The compound was prepared from dibenzoylmethane and o-aminophenol. The V02+ complex with (102) has also been shown to be involved in antiferromagnetic exchange with J = —139 cm-1. Revenko and Gerbeleu prepared several V02+ complexes of (103) derived from Hsal and thiosemicarbazide which were reported to involve ONS coordination.778 The measured were 1.27, 1.21 and 1.33 BM for R = H, Cl and Br, respectively. The complexes are not anhydrous and a dimeric structure (104) was proposed. 

Was prepd by Meldola Hay(Ref 2) by diazotiza-tion of 2,3,6-trinitro-4-aminophenol with NaNOj in acid soln. Because of its high sensitivity, the props of this compd were not detd Refs l)Beil 16,531 2)R.Meldola J.G.Hay,... 

Figure 7.15 Chromatogram of the separation of (1) /j-aminophcnol, (2) o-aminophenol, and (3) m-aminophenol, (A) without treatment and (B) after PDADMAC gold coating chips [34].

Carrillo, J. R. Diez-Barra, E. A simple preparation of O-substituted o-aminophenols. Synth. Commun. 1994, 24, 945—950. 

Oclarit, J. M., Shinji, O., Kazuo, K., Yukiho, Y., and Susumu, I., Production of an antibacterial agent, o-aminophenol, by a bacterium isolated from the marine sponge, Adocia sp., Fish Sci., 60, 559, 1994. 

Robinson D, Smith JN, Wiliams RT. 1951b. Studies in detoxication. 40. o-, m-and p-Nitrophenols, o-, m- and p-aminophenols and 4-nitrocatechol as metabolites of nitrobenzene. Biochem J 50 228-235. 

Maurino V, Minero C, Pelizzetti E, Piccinini P, Serpone N, Hidaka H. The fate of organic nitrogen under photocatalytic conditions degradation of nitrophenols and aminophenols on irradiated Ti02. J Photochem Photobiol A Chem 1997 109 171-6. 

Pulgarin, C. and J. Kiwi (1995). Iron oxide-mediated degradation, photodegradation, and biodegradation of aminophenols. Langmuir, 11(2), 519-526. 

Sainthorant C, Morin P, Dreux M, Baudry A, Goetz N. Separation of phenylenedia-mine, phenol and aminophenol derivatives by micellar electrokinetic chromatography. comparison of the role of anionic and cationic surfactants. J Chromatogr A 1995 717 167. 

Hodgkin, J. H., Linear aminophenol polymers using the Mannich reaction, J. Polym. Sd. Polym. Chem. Fd.. 24, 3117, 1986. 

Xing X, Wua J, Dai W-M (2006) Acid-mediated three-component aza-Diels-Alder reactions of 2-aminophenols under controlled microwave heating for synthesis of highly functionalized tetrahydroquinolines. Part 9 Chemistry of aminophenols. Tetrahedron 62 11200-11206... 

Kiese, M., Weger, N. (1969). Formation of ferrihaemoglobin with aminophenols in the human for the treatment of cyanide poisoning. Eur. J. Pharmacol. 7 97-105. 

Ermer, O. and Eling, A., Molecular recognition among alcohols and amines Super-tetrahedral crystal architectures of linear diphenol-diamine complexes and aminophenols, J. Chem. Soc. Perkin Trans. II925-944 (1994). 

---