PRODUCTS

2-NAPHTHYLAMINE

CAS NO:91-59-8
EC NO:202-080-4

Preparation
2-Naphthylamine is prepared by heating 2-naphthol with ammonium zinc chloride to 200-210 °C, the Bucherer reaction.
2-Naphthylamines acetyl derivative can be obtained by heating 2-naphthol with ammonium acetate to 270-280 °C.

Properties
Chemical formula:   C10H9N
Molar mass:   143.189 g·mol−1
Appearance:   White to red crystals
Odor:   odorless
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)
Solubility in water:   miscible in hot water
Vapor pressure:   1 mmHg (107° C)
Acidity (pKa):   3.92
Magnetic susceptibility (χ):   -98.00·10−6 cm3/mol

2-Naphthylamine is a synthetic, air-sensitive, colorless crystalline solid that is soluble in hot water, alcohol, ether and many organic solvents. Currently, it is only used in laboratory research. Because the commercial production and use of 2-naphthylamine are banned, the potential for human exposure is low. The general population may be exposed to this chemical through inhalation of emissions from sources where nitrogen-containing organic matter is burned, such as coal furnaces and cigarettes. At greatest risk of occupational exposure to 2-naphthylamine are laboratory technicians and scientists who use it in research. Acute inhalation exposure to high levels of 2-naphthylamine can result in methemoglobinemia, dyspnea, ataxia, hematuria, dysuria and hemorrhagic cystitis.
2-Naphthylamine is known to be a human carcinogen.

2-naphthylamine is a naphthylamine carrying the amino group at position 2.
2-Naphthylamine has a role as a carcinogenic agent.

2-Naphthylamine appears as a white to reddish colored solid in the form of flakes. Slightly soluble in hot water and denser than water. Toxic by ingestion, inhalation and skin absorption. Used to make dyes and agricultural chemicals.

Uses
Rarely used today;
used in the past in research and in the production of dyes and rubber.

Formula: C10H9N
Molecular mass: 143.2
Boiling point: 306°C
Melting point: 110.2-113°C
Density: 1.061 g/cm³
Solubility in water: poor
Relative vapour density (air = 1): 4.95
Flash point: 157°C
Octanol/water partition coefficient as log Pow: 2.28

2-Naphthylamine formerly was used commercially as an intermediate in the manufacture of dyes, as an antioxidant in the rubber industry, and to produce 2-chloronaphthalene.

Research chemical; component of cigarette smoke. Formerly used as a chemical intermediate for dyes, as a rubber antioxidant, and in the production of 2-chloronaphthylamine.

2-Naphthylamine belongs to the class of organic compounds known as naphthalenes.
Naphthalenes are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
2-Naphthylamine is formally rated as a carcinogen (by IARC 1) and is also a potentially toxic compound. Based on a literature review a significant number of articles have been published on 2-Naphthylamine.

2-Naphthylamine is an aromatic amine.
2-Naphthylamine is used to make azo dyes.
2-Naphthylamine 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.
2-Naphthylamine forms odorless, colorless plates which melt at 111-112 °C.
2-Naphthylamine 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 amines; it is strongly alkaline in reaction, has an ammoniacal odor and cannot be diazotized. On oxidation it yields ortho-carboxy-hydrocinnamic acid, HO2C•C6H4•CH2•CH2•CO2H. Numerous sulfonic acids 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.

2-Naphthylamine Hydrochloride is listed as a known human carcinogen used in the manufacturing of dyes and as antioxidant in rubber.

2-Naphthylamine is also known as β-Naphthylamine, it is white to pink shiny flaky crystal, it is volatile with water vapor.
2-Naphthylamine is harmful, carcinogenic, the International Institute for Cancer Research (IARC) put benzidine, 2-Naphthylamine and 4-aminobiphenyl as a human carcinogen (evidence), we should be particularly careful. The relative density is 1.0614 (98/4℃), m.p. is 111~113℃, boiling point is 306℃.

2-Naphthylamine is insoluble in water, but soluble in hot water, ethanol, ether and benzene etc. Aqueous solution is blue fluorescence.
2-Naphthylamine can be reducted by heat silver nitrate ammonia solution.
2-Naphthylamine is synthesized by 2-naphthol with ammonia and ammonium sulfite in a high pressure system.
2-Naphthylamine is an important dye intermediates, can be used in the manufacture of dyes, phthalocyanine dyes, reactive dyes (Reactive brilliant orange K-7R, active golden XG, active golden KM-G, Reactive Yellow KM-RN, big red group B) and J acid.
2-Naphthylamine can also be used as organic analytical reagents and fluorescent indicator, and also as a synthesis of organic materials.
2-Naphthylamine can enter from the respiratory tract, gastrointestinal tract and skin. Long-term exposure β-Naphthylamine can cause bladder cancer.
2-Naphthylamine can cause weak stimulation of the skin, contact dermatitis, and methemoglobinemia. After the diagnosis of bladder cancer should be early surgery. Prevention should be carried out from the reform process firstly, 1-naphthylamine acetic acid should be used in place of β-Naphthylamine. Production equipment should be tightly closed to prevent the escape of toxic vapors and dusts.

Amino and nitrite of Aminonaphthalene can form diazonium salt, and can turn into a variety of hydrocarbon derivatives of naphthalene, it can be used in the manufacture of dyes and organic synthesis, also used as indicators of organic analytical reagents and fluorescent agents.

Since the nitration of naphthalene can not obtain 2-nitro-naphthalene, so the producing methods is different from 1-Naphthylamine.
2-Naphthylamine is derived by 2-naphthol pressurized ammonia solution.

Chemical Properties
2-Naphthylamine is a white to red crystals with a faint, aromatic odor. Darkens in air to a reddish-purple color.

Physical properties
White crystals becomes purplish-red on exposure to air. Odor threshold concentrations ranged from 1.4 to 1.9 mg/m3 (quoted, Keith and Walters, 1992).

Uses
2-Naphthylamine is listed as a known human carcinogen. Used in manufacturing of dyes, as antioxidant in rubber

An amine compound used for research purposes

2-Naphthylamine was widely used in themanufacture of dyes and in rubber. Currently, its use is curtailed because of thehealth hazard.

ChEBI:
2-naphthylamine is a naphthylamine carrying the amino group at position 2.
2-naphthylamine has a role as a carcinogenic agent.

A white to reddish colored solid in the form of flakes. Slightly soluble in hot water and denser than water. Toxic by ingestion, inhalation and skin absorption. Used to make dyes and agricultural chemicals.

Major Application
Microelectronics, power transmission & fluid, insulators for electronic devices, photoresists, display device, imaging process, semiconductors, diesel fuel additives, battery, adhesive, paints, inks, chalk, leather, textiles, dye synthesis, soil products

2-naphthylamine is listed as a known human carcinogen. Used in manufacturing of dyes, as antioxidant in rubber.

2-Naphthylamine is an aromatic amine used to make azo dyes. A common reason that it is used less for this purpose is that the substance is a carcinogen.

Physical State :Solid
Solubility :Soluble in Ethyl Acetate and Methanol
Storage :Store at 4° C
Melting Point :111-113° C (lit.)
Boiling Point :306° C (lit.)
Density :1.06 g/cm3 at 25° C

2-Naphthylamine is one of two isomeric aminonaphthalenes, compounds with the formula C10H7NH2.
2-Naphthylamine is a colorless solid, but samples take on a reddish color in air because of oxidiation. The aromatic amine used to be used to make azo dyes.
2-Naphthylamine is a known carcinogen and has largely been replaced by less toxic compounds.
2-Naphthylamine is also known as β-Naphthylamine, it is white to pink shiny flaky crystal, it is volatile with water vapor.
2-Naphthylamine is harmful, carcinogenic, the International Institute for Cancer Research (IARC) put benzidine, 2-Naphthylamine and 4-aminobiphenyl as a human carcinogen (evidence), we should be particularly careful. The relative density is 1.0614 (98/4℃), m.p. is 111~113℃, boiling point is 306℃.
2-Naphthylamine is insoluble in water, but soluble in hot water, ethanol, ether and benzene etc. Aqueous solution is blue fluorescence. Amino and nitrite of Aminonaphthalene can form diazonium salt, and can turn into a variety of hydrocarbon derivatives of naphthalene, it can be used in the manufacture of dyes and organic synthesis, also used as indicators of organic analytical reagents and fluorescent agents.

IUPAC names:
2-aminonaphthalene
2-Naphthylamin
2-Naphthylamine
2-naphthylamine
naphthalen-2-amine

SYNONYMS:
Naphthalen-2-amine [Wiki]
202-080-4 [EINECS]
2-Aminonaftalen [Czech]
2-amino-naphthalene
2-Aminonaphthalene
2-naftilamina [Portuguese]
2-Naftylamin [Czech]
2-Naftylamine [Dutch]
2-Naphtalénamine [French] [ACD/IUPAC Name]
2-Naphthalenamine [ACD/Index Name] [ACD/IUPAC Name]
2-Naphthalinamin [German] [ACD/IUPAC Name]
2-Naphthylamin [German]
2-naphthylamine
91-59-8 [RN]
CKR7XL41N4
MFCD00004112 [MDL number]
Naphthalen-2-amin
QM2100000
β-Naftalamin [Czech]
β-naftilamina [Italian]
β-Naftylamin [Czech]
β-Naftyloamina [Polish]
β-Naphthylamin [German]
β-Naphthylamine
2-AMINONAPHTHALENE
2-Naphthalenamine
2-NAPHTHYLAMINE
2-NAPHTHYLAMINE (BETA-)
AKOS AUF0416
BETA-NAPHTHYLAMINE
B-NAPHTHYLAMINE
c.i. 37270
Fast Scarlet Base B
β-Naphthylamine β-Aminonaphthalene
2-Aminonaftalen
2-aminonaftalen(czech)[qr]
2-aminonaphthalene[qr]
2-Naftylamin
2-Naftylamine
2-naftylamine[qr]
2-Naphalenamine
2-Naphthalamine
2-naphthalenamine[qr]
2-Naphthylamin