2-Naphthylamine
Encyclopedia
2-Naphthylamine is an aromatic amine
. It is used to make azo dyes. It is a known human carcinogen
and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol
with ammonium
zinc chloride
to 200-210 °C; or in the form of its acetyl
derivative by heating 2-naphthol with ammonium
acetate
to 270-280 °C. It forms odorless, colorless plates which melt at 111-112 °C. It gives no color with ferric chloride. When reduced by sodium
in boiling amyl alcohol
solution it forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the aliphatic
amine
s; it is strongly alkaline in reaction, has an ammonia
cal odor and cannot be diazo
tized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2C•C6H4•CH2•CH2•CO2H. Numerous sulfonic acid
s
derived from 2-naphthylamine are known. Of these, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.
smoke and suspected to contribute to the development of bladder cancer
.
It is activated in the liver but quickly deactivated by conjugation to glucuronic acid
. In the bladder, glucuronidase
re-activates it by deconjugation, which leads to the development of bladder cancer.
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
. It is used to make azo dyes. It is a known human carcinogen
Carcinogen
A carcinogen is any substance, radionuclide, or radiation that is an agent directly involved in causing cancer. This may be due to the ability to damage the genome or to the disruption of cellular metabolic processes...
and has largely been replaced by less toxic compounds. 2-Naphthylamine is prepared by heating 2-naphthol
Naphthol
Naphthol may refer to:* 1-Naphthol* 2-Naphthol...
with ammonium
Ammonium
The ammonium cation is a positively charged polyatomic cation with the chemical formula NH. It is formed by the protonation of ammonia...
zinc chloride
Zinc chloride
Zinc chloride is the name of chemical compound with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. ZnCl2 itself is hygroscopic and even deliquescent. Samples should therefore be protected from...
to 200-210 °C; or in the form of its acetyl
Acetyl
In organic chemistry, acetyl is a functional group, the acyl with chemical formula COCH3. It is sometimes represented by the symbol Ac . The acetyl group contains a methyl group single-bonded to a carbonyl...
derivative by heating 2-naphthol with ammonium
Ammonium
The ammonium cation is a positively charged polyatomic cation with the chemical formula NH. It is formed by the protonation of ammonia...
acetate
Acetate
An acetate is a derivative of acetic acid. This term includes salts and esters, as well as the anion found in solution. Most of the approximately 5 billion kilograms of acetic acid produced annually in industry are used in the production of acetates, which usually take the form of polymers. In...
to 270-280 °C. It forms odorless, colorless plates which melt at 111-112 °C. It gives no color with ferric chloride. When reduced by sodium
Sodium
Sodium is a chemical element with the symbol Na and atomic number 11. It is a soft, silvery-white, highly reactive metal and is a member of the alkali metals; its only stable isotope is 23Na. It is an abundant element that exists in numerous minerals, most commonly as sodium chloride...
in boiling amyl alcohol
Amyl alcohol
An amyl alcohol is any of 8 alcohols with the formula C5H11OH. A mixture of amyl alcohols can be obtained from fusel alcohol. Amyl alcohol is used as a solvent and in esterfication for example in the production of amyl acetate...
solution it forms alicyclic tetrahydro-3-naphthylamine, which has most of the properties of the aliphatic
Aliphatic compound
In organic chemistry, aliphatic compounds are acyclic or cyclic, non-aromatic carbon compounds.Thus, aliphatic compounds are opposite to aromatic compounds.- Structure :...
amine
Amine
Amines are organic compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines,...
s; it is strongly alkaline in reaction, has an ammonia
Ammonia
Ammonia is a compound of nitrogen and hydrogen with the formula . It is a colourless gas with a characteristic pungent odour. Ammonia contributes significantly to the nutritional needs of terrestrial organisms by serving as a precursor to food and fertilizers. Ammonia, either directly or...
cal odor and cannot be diazo
Diazo
Diazo refers to a type of organic compound called diazo compound that has two linked nitrogen atoms as a terminal functional group. The general formula is R2C=N2. The simplest example of a diazo compound is diazomethane...
tized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2C•C6H4•CH2•CH2•CO2H. Numerous sulfonic acid
Sulfonic acid
Sulfonic acid usually refers to a member of the class of organosulfur compounds with the general formula RS2–OH, where R is an alkyl or aryl. The formal part of acid, HS2–OH, are formally derivatives of the "parent" inorganic compound with the formula HSO2.-Preparation:Sulfonic acid is...
s
derived from 2-naphthylamine are known. Of these, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.
Role in disease
2-Naphthylamine is found in cigaretteCigarette
A cigarette is a small roll of finely cut tobacco leaves wrapped in a cylinder of thin paper for smoking. The cigarette is ignited at one end and allowed to smoulder; its smoke is inhaled from the other end, which is held in or to the mouth and in some cases a cigarette holder may be used as well...
smoke and suspected to contribute to the development of bladder cancer
Bladder cancer
Bladder cancer is any of several types of malignant growths of the urinary bladder. It is a disease in which abnormal cells multiply without control in the bladder. The bladder is a hollow, muscular organ that stores urine; it is located in the pelvis...
.
It is activated in the liver but quickly deactivated by conjugation to glucuronic acid
Glucuronic acid
Glucuronic acid is a carboxylic acid. Its structure is similar to that of glucose. However, glucuronic acid's sixth carbon is oxidized to a carboxylic acid...
. In the bladder, glucuronidase
Glucuronidase
Beta-glucuronidases are members of the glycosidase family of enzymes that catalyze breakdown of complex carbohydrates. Human β-glucuronidase is a type of glucuronidase that catalyzes hydrolysis of β-D-glucuronic acid residues from the non-reducing end of mucopolysaccharides such as heparan sulfate...
re-activates it by deconjugation, which leads to the development of bladder cancer.
See also
- NaphthaleneNaphthaleneNaphthalene is an organic compound with formula . It is a white crystalline solid with a characteristic odor that is detectable at concentrations as low as 0.08 ppm by mass. As an aromatic hydrocarbon, naphthalene's structure consists of a fused pair of benzene rings...
- NaphtholNaphtholNaphthol may refer to:* 1-Naphthol* 2-Naphthol...
- 1-Naphthylamine1-Naphthylamine1-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...
- 1,8-Bis(dimethylamino)naphthalene1,8-Bis(dimethylamino)naphthalene1,8-Bisnaphthalene is a chemical compound that was first prepared in 1968 by Roger Alder FRS at the University of Bristol. It is often referred by the trade name Proton Sponge, a trademark of Sigma-Aldrich. This compound is a diamine in which the two dimethylamino groups are attached on the same...