1-Naphthylamine

1-Naphthylamine

Chembox new
Name = 1-Naphthylamine
ImageFile = 1-Naphthylamine.png ImageSize = 120px
ImageName = 1-Naphthylamine
IUPACName = 1-Aminonaphthalene
OtherNames = 1-Naphthylamine
α-Naphthylamine
Section1 = Chembox Identifiers
CASNo = 134-32-7
PubChem = 8640
SMILES = NC2=CC=CC1=CC=CC=C12
Section2 = Chembox Properties
Formula = C10H9N
MolarMass = 143.19 g/mol
Density = 1.114 g/cm³
MeltingPt = 47-50 °C
BoilingPt = 301 °C

1-Naphthylamine is an aromatic amine. It can be prepared by reducing 1-nitronaphthalene with iron and hydrochloric acid at about 70 °C, the reaction mixture being neutralized with milk of lime, and the naphthylamine steam-distilled. It may also be prepared, in the form of its acetyl derivative, by heating 1-naphthol with sodium acetate, ammonium chloride and acetic acid; by heating 1-naphthol with calcium chloride-ammonia to 270 °C; and by heating pyromucic acid, aniline, zinc chloride and lime to 300 °C. It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. Oxidizing agents, such as ferric chloride, give a blue precipitate with solutions of its salts. Chromic acid converts it into 1-naphthoquinone. Sodium in boiling amyl alcohol reduces it to aromatic tetrahydro-1-naphthylamine, a substance having the properties of an aromatic amine, for it can be diazotized and does not possess an ammoniacal smell. Since it does not form an addition product with bromine, reduction must have taken place in one of the nuclei only, and on account of the aromatic character of the compound it must be in that nucleus which does not contain the amino group. This tetrahydro compound yields adipic acid, (C6O4H10), when oxidized by potassium permanganate. The 1-naphthylamine sulfonic acids are used for the preparation of azo dyes, these dyes possessing the important property of dyeing unmordanted cotton. The most important is naphthionic acid, 1-amino-4-sulfonic acid, produced by heating 1-naphthylamine and sulfuric acid to 170-180 °C with about 3% of crystallized oxalic acid. It forms small needles, very sparingly soluble in water. With diazotized benzidine it gives Congo red.

ee also

*Naphthalene
*Naphthol
*2-Naphthylamine
*1,8-Bis(dimethylamino)naphthalene

References


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  • Naphthylamine — Naph thyl*am ine, n. (Chem.) One of two basic amido derivatives of naphthalene, {C10H7.NH2}, forming crystalline solids. [1913 Webster] …   The Collaborative International Dictionary of English

  • Naphthylamine — (Amidonaphthaline) C10H7.NH2, die dem Anilin entsprechenden Amidoderivate des Naphthalins. αNaphthylamin entsteht aus Nitronaphthalin bei Einwirkung von Eisen und Salzsäure und beim Erhitzen von αNaphthol mit Chlorzinkammoniak auf 250°, auch beim …   Meyers Großes Konversations-Lexikon

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  • naphthylamine — naph·thyl·amine naf thil ə .mēn, nap n either of two isomeric crystalline bases C10H9N that are used esp. in synthesizing dyes esp one ( ß naphthylamine) with the amino group in the beta position that has been demonstrated to cause bladder cancer …   Medical dictionary

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  • naphthylamine — naftilaminas statusas T sritis chemija formulė C₁₀H₇NH₂ atitikmenys: angl. naphthylamine rus. нафтиламин …   Chemijos terminų aiškinamasis žodynas

  • naphthylamine — noun Etymology: International Scientific Vocabulary Date: 1857 either of two isomeric crystalline bases C10H9N used especially as dye intermediates …   New Collegiate Dictionary

  • naphthylamine — noun Either of two isomeric primary amines derived from naphthalene; they occur in crude oil, and are used in the preparation of dyes and other compounds …   Wiktionary

  • naphthylamine — naph·thyl·amine …   English syllables

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