Naphthyl amine naphthylamine

Physical properties. Majority are liquids except p toluidine and 1- and 2-naphthylamine. All are colourless when pure, but rapidly darken on exposure to air and light. All are very sparingly soluble in water, but dissolve readily in dilute mineral acids (except the naphthyl-amines, which are only moderately soluble in adds). They form colourless crystalline salts e.g., CjHjNH2,HCl) which are soluble in water these aqueous solutions usually have an add reaction owing to hydrolysis, and give the reactions of both the amine and the acid from which they are derived. Addition of alkali to the acid solution liberates the amine. 

Naphtyl, n. naphthyl, -amin, n. naphthylamine. -aminsulfosaure, /. naphthylaminesulfonic acid, -blsu, n. naphthyl blue. 

Dinitronaphthalene (Delta-dinitronaphtha-lenet 1,6-DNN). Crysts from acet ac, mp 166-67°, bp at 10mm 235°, 360° with decompn (Refs 2 31) CA Registry No 60746-5. It is prepd by the nitration of 2-nitronaphtha- ene with nitric ac/sulfuric ac in hot acet ac (Ref 21) by diazotization of 5-nitro-2-naphthyl-amine followed by treatment of the diazonium salt with Na cobaltinitrite, yield 40% (Ref 36) or by removal of the amino group from 1,6-dinitro-2-naphthylamine by diazotization followed by redn (Ref 17). The temp of expin is 492°(Refl7)... 

From photoreduction (> 280 nm) in diethylamine, low yields of 1-naphthyl-amine and the corresponding azo- and azoxy compounds have been obtained Photolysis (366 nm) in acidified 50% aqueous 2-propanol at varied HCl-concentrations results in remarkable enhancement of photoreduction compared to neutral 2-propanol. The highest disappearance quantum yield measured was 1.28 X 10 2 for 6 M HCl 4-chloro-l-naphthylamine is formed as main product 74.75). 

S5Tionyms AI3-02912 AIDS-18992 2-Aminonaphthalene BNA CCRIS 424 C.I. 37270 EINECS 202-080-4 Fast scarlet base B 2-Naphthalamine 2-Naphthalenainine P-Naphthyl-amine 6-Naphthylamine 2-Naphthylamine mustard NSC 4153 RCRA waste number U168 UN 1650 USAF CB-22. 

Dinitro-1,1 -azonaphthaiene orn-red rods (from benz). mp 219° prepd bv oxidn of. 2-nitro-l-naphthylamine with phenyl iodo-soacetate yielding also naphthofurazan, identical with the product obtd by oxidg 1-nitr o-2-naphthyl amine (Ref 8)... 

Interaction of the same 1-benzy 1-3-methyl-substituted salt 184 with morpholine leads to a-naphthylamine 187 in ethanol and to the mixture of a-(187) and 8- (188) naphthyl-amines in a ratio depending on the temperature if morpholine itself was used as a solvent (88MI1 88UP1). 

Miuoinapninyiamme conuensanvn iOuvci (no formula is given). A solid which can be prepd from a soln of a mixt of 1.5 mol of aldol-a-naphthylamine and 0.5 mol of aldol-f - naphthyl amine in 1.5 mols of dil HCi with 1.5 mols of acetaldehyde. This was followed by neutralization, filtering, purification and drying... 

SYNS l-DIMETHYLAMINONAPHTHALENE DIMETHYL-a-NAPHTHYLAMINE tt-DIMETHYL-NAPHTHYLAMINE N,N-DLMETHYL-a-NAPHTHYL-AMINE... 

The following derivatives are stable towards ammonium sulphide p - acetoxymercuri-o-nitroaniline, o - acetoxy mereuri-p-broniodimethyl-aniline, 2 4-diacetoxyniereuri-a-naphthylaniine, and p-dimethylamino-phenylmercuric acetate. If the latter compound be boiled with potassium iodide solution, then treated with hydrogen sulphide, only traces of mercuric sulphide are produced. Mercury compounds from jS-naphthylamine, j8-naphthylamine-C-sulphonic acid, 1 5-naphthyl amine sulphonic acid are decomposed b ammonium suli hide, wiiilst naphthi-onic acid derivatives are only slowty attacked. 

The attempted intramolecular cyclization of the substituted naphthylamines XVI failed and led only to an intermolecular coupling [92]. 4-Substituted diphenylamines form in a remarkable cyclodimerization 5,10-dihydro-5,10-diphenylphenazines [Eq. (10)] [84], One requirement is that all para positions must be substituted by groups that are not eliminated and not strongly electron withdrawing. Yields are increased by electrolyzing at low current densities. Di-(2-naphthyl)amine undergoes the same reaction anodically, but... 

This method is essentially that described by Goldhahn. 4-Nitro-l-naphthylamine has also been prepared by the nitration of a-naphthylamine, acetyl-a-naphthylamine, and ethyl-1-naphthyloxamate, by the oxidation of 4-nitroso-l-naphthyl-amine, and by reaction of 4-chloro-l-nitronaphthalene with ammonia. ... 

By the action of concentrated sulphuric acid on y3-naphthyl-amine two monosulphonic acids are first formed, 9-naphthylaminc-a-sulphonic acid (corresponding to the crocein acid from -naph-thol), and the yS-naphthylamine-7-sulphonic acid. 

Investigation of the fluorescence quenching of 2-aminobenzoic acid (78), 1-naphthyl-amine (79), 2-naphthylamine (80), IV-phenyl-1-naphthyl amine (81) and anilines allows the... 

Derivation By sulfonation of either 2-naphthyl-amine-5-sulfonic acid or 2-naphthylamine-7-sul-fonic acid. 

Derivation (3-naphthylamine sulfate is sulfonated with 66% oleum, the filtrate yields 2-naphthyl-amine-l,5,7-trisulfonic acid. On reaction with dilute sulfuric acid at 125C, this yields 2-naphthylamine-5,7-disulfonic acid from this J acid is obtained on reaction with 58% sodium hydroxide solution at 200C and 210 psi. 

Cassella s Acid F. 7-Amino-2-naphthalenesul-foitic add 2-naphthylamine-7-sulfonic add 0-naphthyl-amine-6 -sulfonic acid. CwHjNOjS mol wt 223.26. C... 

Amination of aromatic nitro compounds often occurs smoothly and directly also on condensation with hydroxylamine in alkaline solution, the amino group normally entering ortho or para to the nitro group. One nitro group activates naphthalene derivatives sufficiently, but in the benzene series two are necessary to induce this reaction. 2-Nitro-l-naphthylamine was thus obtained (80%) from 2-nitronaphthalene,400 and 4-nitro-l-naphthyl-amine (60%) from 1-nitronaphthylamine.401 The amino group also enters the nitrated ring of quinoline derivatives. 

Good yields of iV-aryl-l-naphthylamines are also obtained by using catalytic amounts of iodine with, e.g., 1-naphthylamine and aniline, the toluidines, m- and /7-chloroaniline, o- and /j-anisidine,1045 2,3- or 3,4-dimethylaniline.1122 Di-(2-naphthylamine) is obtained almost quantitatively when 2-naphthyl-amine is heated for 4 hours at 230° in the presence of 0.5-1.0% of iodine, and 4,4 -dihydroxydiphenylamine in 70% yield from />-aminophenol under similar conditions.1045... 

With 2-naphthylamine and its derivatives there is a further possible method of transamination they can be converted into N-alkyl- and JV-aryl-2-naphthyl-amines reversibly by a type of Bucherer reaction (cf. page 531). 

Rodriguez and coworkers compared the behavior of other nitroaromatic amines, like 4-nitro-1-naphthylamine, N-acetyl-4-nitro-l-naphthyl-amine, and N,N-dimethyl-4-nitroaniline with 4-nitroaniline. The rate and quantum yield of the polymerizations as well as the residual unsaturation in the products were found to be strongly dependent on the nature of the photo-... 

Acetaldehyde added with cooling to a mixture of 2-hydroxybenzal-2-naphthyl-amine, some 2-naphthylamine hydrochloride, and alcohol, then heated in a sealed tube for 1-3 hrs. in a boiling water bath 2-(2-hydroxyphenyl)-5,6-benzoquinoline. Y 50.0%. F. e. s. N. S. Kozlov and I. A. Shur, 7K. 29, 3779 (1959) G. A. 54, 19677c. 

BETA-NAPHTHYL- AMINE C H.N 2-Naphthylamine 2-Amino-naphthalene Not available Com-busl Ible solid ... 

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