P-naphthylamines

The amlnation reaction is reversible thus P-naphthylamine can be reconverted into p-naphthol by heating with aqueous sodium bisulphite solution, then adding alkali and boiling until all the ammonia is expelled. 

Thus good yields (> 60 per cent) are obtained with aniline and methyl, ethyl, n-propyl and n-butyl phosphates with a- and P-naphthylamine and methyl or ethyl phosphate nuclear substituted anilines and methyl or ethyl phosphate. 

Methylaniline Ethylaniline n-Propylaniline n-Butylaniline Benzylaniline 2 -MethyIbenzylamine N-Ethylbenzylamine 2 -Methyl o-toluidine N-Methyl m-toluidine 2 -MethyI p-toluidine N-Ethyl o-toIuidine N-Ethyl m-toIuidine 2S -Ethyl p-toluidine 2 -MethyI a-naphthylamine N-Methyl p-naphthylamine N-Phenyl- a-naphthylamine 2 -Phenyl-P-naphthylamine... 

Acetyl-o-aniaidine Acetyl-m-anisidine Acetyl-p-anisldine Acetyl-o-phenetidine Acetyl-m-phenetidine Acetyl-p-phenetidine (or phenacetin) Acetyl-a-naph thy lam ine Acetyl- p-naphthylamine... 

Solubility in 5 per cent, hydrochloric acid. Add the acid to 0 10 g. of the solid or 0 20 ml. of the liquid in quantities of 1 0 ml. until 3 0 ml. have been introduced. Some organic bases (e.g., p-naphthylamine) form hydrochlorides that are soluble in water but are precipitated by an excess of acid if solution occurs at any time, the unknown is assigned to Group IV. If the compound appears insoluble, remove some of the supernatant liquid by means of a dropper to a semimicro test-tube (75 X 10 mm.), and add 5 per cent, sodium hydroxide solution until basic and observe whether any precipitate is produced the formation of a precipitate will place the compound in Group IV. 

Phenylnaphthylamines W-Phenyl-p-naphthylamine (11) Yes Once widely used in rubber industry because of good all-round effect in diene rubbers. Now almost obsolete. 

Carcinogens Cancer-producing agents Skin Respiratory Bladder/urinary tract Liver Nasal Bone marrow Coal tar pitch dust crude anthracene dust mineral oil mist arsenic. Asbestos polycyclic aromatic hydrocarbons nickel ore arsenic bis-(chloromethyl) ether mustard gas. p-naphthylamine benzidine 4-am i nodi pheny lam ine. Vinyl chloride monomer. Mustard gas nickel ore. Benzene. 

Heating arylamines with carbon dioxide at 200 C (8500 atm) gives good yields of 3-aryl derivatives of 2,4-dihydroxyquinazoline ° (see 5e). The method is unsatisfactory when riitro, halo, and phenolic anilines and a- or p-naphthylamines are used. 

A convenient synthesis of benzo[g]quinoline via the condensation of P-naphthylamine with malondialdehyde followed by cyclization in pol5q>hosphoric acid was reported <95H(41)2221>. 

P-Nitronaphthalene is not formed by direct nitration. For the preparation of p-naphthylamine, the Bucherer reaction may be applied to p-naphthol, i.e., by heating with ammoniacal ammonium sulphite solution at 150° (under pressure). The reaction involves the addition of the bisulphite to the keto form of p-naphthol ... 

P-Bromonaphthalene. The preparation from p-naphthylamine, which has carcinogenic properties, is avoided by the use of 2-naphthylamine-1-sulphonic acid ( 2-amino-1-naphthalenesulphonic acid ) the latter is obtained commercially by cautious treatment of p-naphthol with sulphuric acid—the SOjH group first enters the 1-position—followed by the Bucherer reaction. Diazotisation and reaction with cuprous bromide yields 2-bromonaphthalene-l-sulphonic acid heating with sulphuric acid eliminates the sulphonic acid group to give 2-bromonaphthalene. 

Ethy Ibenzy lamine A -Methyl o-toluidine A -Methyl m-toluidine. 2V-Methyl p-toluidine A -Ethyl o-toluidine -Ethyl m-toluidine -Ethyl p-toluidine 2V-Methyl a-naphthylamine 2V-Methyl p-naphthylamine 2V-Phenyl- a-naphthylamine N-Phenyl- p-naphthylamine... 

The substance may be obtained from p-naphthylamine (Section IV,38) by the procedure described imder p Tolunitrile (Section IV,66). 

One of the earliest organic antioxidants, now obsolescent due to its severe staining properties, health problems, and to the production of more effective antioxidants. Phenyl-p-Naphthylamine... 

Historically, bladder tumors have been associated with exposures in the aniline dye industry. However, conclusive evidence for any one particular exposure could not be obtained in these studies since the workers were exposed to many chemicals within the same work area. For example, Case et al. (1954) investigated the incidence of bladder tumors among British workers in the chemical dye industry. In addition to aniline, the workers were exposed to other aromatic amines, including a- and P-naphthylamine, benzidine, and auramine. Although exposures could not be quantified, there was insufficient evidence to suggest that aniline was a cause of bladder cancers. More recent studies indicate that P-naphthylamine, 4-aminodiphenyl, 4-nitrodiphenyl, 4,4-diaminodiphenyl, or o-toluidine may be involved in increased cancers in the dye industry (Ward et al. 1991 Benya and Cornish 1994). 

Use Rat poison. Banned in Britain due to carcinogenic impurities such as p-naphthylamine (Cremlyn, 1991). 

Naphthol-TV-methylcarbamate, see Carbaryl 6-Naphthylamine, see 2-Naphthylamine a-Naphthylamine, see l-Naphthylamine alpha-Naphthylamine, see l-Naphthylamine p-Naphthylamine, see 2-Naphthylamine... 

Transformation of P-naphthols to P-naphthylamines using ammonium sulfite. 

ANTU was not carcinogenic in rodent feeding studies. Cases of bladder tumors among rat catchers exposed to ANTU have been attributed to P-naphthylamine, a manufacturing impurity of ANTU. In bacterial assays ANTU induced mutations. 

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