Names | |
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Preferred IUPAC name Naphthalen-2-ylamine | |
Other names 2-Naphthaleneamine 2-Aminonaphthalene β-Naphthylamine β-Aminonaphthalene | |
Identifiers | |
3D model (JSmol) | |
606264 | |
ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard | 100.001.892 |
EC Number |
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165176 | |
KEGG | |
PubChem CID | |
RTECS number |
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UNII | |
UN number | 1650 |
CompTox Dashboard (EPA) | |
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Properties | |
C10H9N | |
Molar mass | 143.189 g·mol−1 |
Appearance | White to red crystals [1] |
Odor | odorless [1] |
Density | 1.061 g/cm3 |
Melting point | 111 to 113 °C (232 to 235 °F; 384 to 386 K) |
Boiling point | 306 °C (583 °F; 579 K) |
miscible in hot water [1] | |
Vapor pressure | 1 mmHg (107°C) [1] |
Acidity (pKa) | 3.92 |
-98.00·10−6 cm3/mol | |
Hazards | |
GHS labelling: | |
Danger | |
H302, H350, H411 | |
P201, P202, P264, P270, P273, P281, P301+P312, P308+P313, P330, P391, P405, P501 | |
Flash point | 157 °C; 315 °F; 430 K |
Related compounds | |
Related compounds | 2-Naphthol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). |
2-Naphthylamine or 2-aminonaphthalene is one of two isomeric aminonaphthalenes, compounds with the formula C10H7NH2. It is a colorless solid, but samples take on a reddish color in air because of oxidation. It was formerly used to make azo dyes, but it is a known carcinogen and has largely been replaced by less toxic compounds. [2]
2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C, the Bucherer reaction. Its acetyl derivative can be obtained by heating 2-naphthol with ammonium acetate to 270-280 °C.
It gives no color with iron(III) chloride. When reduced by sodium in boiling amyl alcohol solution, it forms tetrahydro-3-naphthylamine, which exhibits the properties of the aliphatic amines in that it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized.
On oxidation, it yields ortho-carboxy-hydrocinnamic acid, HO2CC6H4CH2CH2CO2H.
Numerous sulfonic acid derivatives of 2-naphthylamine are used in commerce, such as precursors to dyes. [2] Owing to the carcinogenicity of the amine, these derivatives are mainly prepared by amination of the corresponding naphthols. Of them, the δ-acid and Bronner's acid are of more value technically, since they combine with ortho-tetrazoditolyl to produce fine red dye-stuffs.
2-Naphthylamine was previously used as a dye precursor and rubber antioxidant in the 1930s, 40s and 50s. Dupont stopped using it in the 1970s. [3]
2-Naphthylamine is found in cigarette smoke and suspected to contribute to the development of bladder cancer. [4]
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.
Acridine is an organic compound and a nitrogen heterocycle with the formula C13H9N. Acridines are substituted derivatives of the parent ring. It is a planar molecule that is structurally related to anthracene with one of the central CH groups replaced by nitrogen. Like the related molecules pyridine and quinoline, acridine is mildly basic. It is an almost colorless solid, which crystallizes in needles. There are few commercial applications of acridines; at one time acridine dyes were popular, but they are now relegated to niche applications, such as with acridine orange. The name is a reference to the acrid odour and acrid skin-irritating effect of the compound.
Naphthalene is an organic compound with formula C
10H
8. It is the simplest polycyclic aromatic hydrocarbon, and 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. It is the main ingredient of traditional mothballs.
N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.
Aniline is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the simplest aromatic amine. It is an industrially significant commodity chemical, as well as a versatile starting material for fine chemical synthesis. Its main use is in the manufacture of precursors to polyurethane, dyes, and other industrial chemicals. Like most volatile amines, it has the odor of rotten fish. It ignites readily, burning with a smoky flame characteristic of aromatic compounds. It is toxic to humans.
Phthalic anhydride is the organic compound with the formula C6H4(CO)2O. It is the anhydride of phthalic acid. Phthalic anhydride is a principal commercial form of phthalic acid. It was the first anhydride of a dicarboxylic acid to be used commercially. This white solid is an important industrial chemical, especially for the large-scale production of plasticizers for plastics. In 2000, the worldwide production volume was estimated to be about 3 million tonnes per year.
Cyclohexanol is the organic compound with the formula HOCH(CH2)5. The molecule is related to cyclohexane by replacement of one hydrogen atom by a hydroxyl group. This compound exists as a deliquescent colorless solid with a camphor-like odor, which, when very pure, melts near room temperature. Millions of tonnes are produced annually, mainly as a precursor to nylon.
Sudan I is an organic compound typically classified as an azo dye. It is an orange-red solid, used to color waxes, oils, petrol, solvents, and polishes. Historically, Sudan I used to serve as a food coloring agent, notably for curry powder and chili powder. However, along with its derivatives Sudan III and Sudan IV, the compound has been banned in many countries due to its classification as a category 3 carcinogenic hazard by the International Agency for Research on Cancer. Nevertheless, Sudan I remains valuable as a coloring reagent for non-food-related uses, such as in the formulation of orange-colored smoke.
Vanadium(V) oxide (vanadia) is the inorganic compound with the formula V2O5. Commonly known as vanadium pentoxide, it is a dark yellow solid, although when freshly precipitated from aqueous solution, its colour is deep orange. Because of its high oxidation state, it is both an amphoteric oxide and an oxidizing agent. From the industrial perspective, it is the most important compound of vanadium, being the principal precursor to alloys of vanadium and is a widely used industrial catalyst.
Dimethylamine is an organic compound with the formula (CH3)2NH. This secondary amine is a colorless, flammable gas with an ammonia-like odor. Dimethylamine is commonly encountered commercially as a solution in water at concentrations up to around 40%. An estimated 270,000 tons were produced in 2005.
Benzidine (trivial name), also called 1,1'-biphenyl-4,4'-diamine (systematic name), is an organic compound with the formula (C6H4NH2)2. It is an aromatic amine. It is a component of a test for cyanide. Related derivatives are used in the production of dyes. Benzidine has been linked to bladder and pancreatic cancer.
Benzyl chloride, or α-chlorotoluene, is an organic compound with the formula C6H5CH2Cl. This colorless liquid is a reactive organochlorine compound that is a widely used chemical building block.
Ethylamine, also known as ethanamine, is an organic compound with the formula CH3CH2NH2. This colourless gas has a strong ammonia-like odor. It condenses just below room temperature to a liquid miscible with virtually all solvents. It is a nucleophilic base, as is typical for amines. Ethylamine is widely used in chemical industry and organic synthesis. It is a DEA list I chemical by 21 CFR § 1310.02.
Chromyl chloride is an inorganic compound with the formula CrO2Cl2. It is a reddish brown compound that is a volatile liquid at room temperature, which is unusual for transition metal compounds. It is the dichloride of chromic acid.
4-Aminobiphenyl (4-ABP) is an organic compound with the formula C6H5C6H4NH2. It is an amine derivative of biphenyl. It is a colorless solid, although aged samples can appear colored. 4-Aminobiphenyl was commonly used in the past as a rubber antioxidant and an intermediate for dyes. Exposure to this aryl-amine can happen through contact with chemical dyes and from inhalation of cigarette smoke. Researches showed that 4-aminobiphenyl is responsible for bladder cancer in humans and dogs by damaging DNA. Due to its carcinogenic effects, commercial production of 4-aminobiphenyl ceased in the United States in the 1950s.
The Bucherer reaction in organic chemistry is the reversible conversion of a naphthol to a naphthylamine in the presence of ammonia and sodium bisulfite. The reaction is widely used in the synthesis of dye precursors aminonaphthalenesulfonic acids.
1-Naphthylamine is an aromatic amine derived from naphthalene. It can cause bladder cancer. It crystallizes in colorless needles which melt at 50 °C. It possesses a disagreeable odor, sublimes readily, and turns brown on exposure to air. It is the precursor to a variety of dyes.
Ethyl acrylate is an organic compound with the formula CH2CHCO2CH2CH3. It is the ethyl ester of acrylic acid. It is a colourless liquid with a characteristic acrid odor. It is mainly produced for paints, textiles, and non-woven fibers. It is also a reagent in the synthesis of various pharmaceutical intermediates.
o-Anisidine (2-anisidine) is an organic compound with the formula CH3OC6H4NH2. A colorless liquid, commercial samples can appear yellow owing to air oxidation. It is one of three isomers of the methoxy-containing aniline derivative.
1-Naphthol, or α-naphthol, is a organic compound with the formula C10H7OH. It is a fluorescent white solid. 1-Naphthol differs from its isomer 2-naphthol by the location of the hydroxyl group on the naphthalene ring. The naphthols are naphthalene homologues of phenol. Both isomers are soluble in simple organic solvents. They are precursors to a variety of useful compounds.
2-Acetylaminofluorene is a carcinogenic and mutagenic derivative of fluorene. It is used as a biochemical tool in the study of carcinogenesis. It induces tumors in a number of species in the liver, bladder and kidney. The metabolism of this compound in the body by means of biotransformation reactions is the key to its carcinogenicity. 2-AAF is a substrate for cytochrome P-450 (CYP) enzyme, which is a part of a super family found in almost all organisms. This reaction results in the formation of hydroxyacetylaminofluorene which is a proximal carcinogen and is more potent than the parent molecule. The N-hydroxy metabolite undergoes several enzymatic and non-enzymatic rearrangements. It can be O-acetylated by cytosolic N-acetyltransferase enzyme to yield N-acetyl-N-acetoxyaminofluorene. This intermediate can spontaneously rearrange to form the arylamidonium ion and a carbonium ion which can interact directly with DNA to produce DNA adducts. In addition to esterification by acetylation, the N-hydroxy derivative can be O-sulfated by cytosolic sulfur transferase enzyme giving rise to the N-acetyl-N-sulfoxy product.