134-32-7

A crystalline solid or a solid dissolved in a liquid. Insoluble in water and denser than water. Contact may slightly irritate skin, eyes and mucous membranes. May be slightly toxic by ingestion. Used to make other chemicals.

ALPHA-NAPHTHYLAMINE(134-32-7) is incompatible with oxidizing agents. ALPHA-NAPHTHYLAMINE(134-32-7) is also incompatible with nitrous acid. ALPHA-NAPHTHYLAMINE(134-32-7) reduces warm ammoniacal silver nitrate. .

Sensitive to exposure to air and light. Insoluble in water. Napthyl amines can be slowly hydrolyzed, releasing NH3 as a byproduct [N.L. Drake, Org. React. 1, (1942), 105].

Toxic, especially if containing the β isomer; a questionable carcinogen.

Inhalation may cause cyanosis (blue color in lips and under finger nails). Contact with liquid causes local irritation of eyes. Neither ingestion nor contact with skin produces any recognized immediate effects.

α-Naphthylamine is used as an intermediate in dye production; for manufacturing herbicides and antioxidants; in the manufacture of condensation colors, rubber, and in the synthesis of many chemicals, such as α-naphthol, sodium naphthionate; o-naphthionic acid; Neville and Winther’s acid; sulfonated naphthylamines, α-naphthylthiourea (a rodenticide); and N-phenyl- α-naphthylamine.

Special Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire.

If this chemical gets into the eyes, remove any contact lenses at once and irrigate immediately for at least 15 minutes, occasionally lifting upper and lower lids. Seek medical attention immediately. If this chemical contacts the skin, remove contaminated clothing and wash immediately with soap and water. Seek medical attention immediately. If this chemical has been inhaled, remove from exposure, begin rescue breathing (using universal precautions, including resuscitation mask) if breathing has stopped and CPR if heart action has stopped. Transfer promptly to a medical facility. When this chemical has been swallowed, get medical attention. Give large quantities of water and induce vomiting. Do not make an unconscious person vomit.

UN2077 alpha-Naphthylamine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. PGIII.

Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides, nitrous acid, organic anhydrides, isocyanates, aldehydes. Oxidizes on contact with air.

Solid

α-Naphthylamine exists as white needle-like crystals which turn red on exposure to air. Has a weak ammonia-like odor.

Controlled incineration whereby oxides of nitrogen are removed from the effluent gas by scrubber, catalyst, or thermal device. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

White to yellow crystals or rhombic needles with an unpleasant odor. Becomes purplish-red on exposure to air. Odor threshold concentrations were 140–290 μg/m³ (quoted, Keith and Walters, 1992).

1-Naphthylamine is used in the manufactureof dyes and tonic prints.

A reagent used to synthesize various dyes used in the textile industry.

1-Naphthylamine is mainly used for the production of 1-naphthol. Other major uses are in the production of aminonaphthalenesulfonic acid dye intermediates and as a component of azo dyes.
1-Naphthylamine can also be used as a starting material to synthesize:
[(S)-HY-Phos], a novel chiral phosphine-phosphoramidite ligand for use in rhodium-catalyzed asymmetric hydrogenation of various functionalized olefins.
N-(naphthalen-1-yl)picolinamide.
Pitnot-2, an inactive analog of clathrin inhibitor Pitstop 2.

ChEBI: 1-naphthylamine is a naphthylamine that is naphthalene substituted by an amino group at position 1. It has a role as a human xenobiotic metabolite.

1-Nitronaphthalene reduction.

There is no information on recent production volumes.1-Naphthylamine is used as a chemical intermediate in the synthesis of a wide variety of chemicals, the most important of which include dyes, antioxidants, and herbicides.
Workers involved in the production of chemicals involving 1-naphthylamine were known to have been exposed. Smokers may also be exposed since cigarette smoke contains about 0.03 mg 1-naphthylamine per cigarette.

Tetrahedron Letters, 25, p. 429, 1984 DOI: 10.1016/S0040-4039(00)99903-9
Chemical and Pharmaceutical Bulletin, 34, p. 1524, 1986 DOI: 10.1248/cpb.34.1524

1-Naphthylamine has been tested for carcinogenic activity in mice, hamsters, and dogs by oral administration, in newborn mice by SC injection, and in mice by bladder implantation. Most of these studies reported negative findings, while a few found marginal or equivocal results. In contrast, with the exception of bladder implantation study, 2-naphthylamine gave positive results in virtually all these studies. Mixed results were reported in various genotoxicity tests. 1-Naphthylamine was positive in the Ames test and in vitro chromosome aberration, negative in micronucleus, cell transformation, and recessive lethal mutation in Drosophila, and inconclusive in sister chromatid exchange assays.

Biological. 1-Naphthylamine added to three different soils was incubated in the dark at 23 °C under a carbon dioxide-free atmosphere. After 308 d, 16.6 to 30.7% of the 1-naphthylamine added to soil biodegraded to carbon dioxide (Graveel et al., 1986). Li and Lee (1999) investigated the reaction of 10 mL of 7 mM 1-naphthylamine with 4 g of a Chalmers soil (pH: 6.5, 11.1% sand, 72.8% silt, 16.0% clay). After 120 h, the soil was washed with acetonitrile and the extractant analyzed using GC/MS. The primary transformation product was a dimer tentatively identified as N-(4-aminonaphthyl)-1-naphthylamine. The investigators hypothesized that the formation of this compound and two other unidentified dimers was catalyzed by minerals present in the soil.
Heukelekian and Rand (1955) reported a 5-d BOD value of 0.89 g/g which is 34.6% of the ThOD value of 2.57 g/g. In activated sludge inoculum, following a 20-d adaptation period, no degradation was observed (Pitter, 1976).
Photolytic. Low et al. (1991) reported that the photooxidation of aqueous primary amine solutions by UV light in the presence of titanium dioxide resulted in the formation of ammonium and nitrate ions.
Chemical/Physical. Kanno et al. (1982) studied the aqueous reaction of 1-naphthylamine and other substituted aromatic hydrocarbons (aniline, toluidine, 2-naphthylamine, phenol, cresol, pyrocatechol, resorcinol, hydroquinone, and 1-naphthol) with hypochlorous acid in the presence of ammonium ion. They reported that the aromatic ring was not chlorinated as expected but was cleaved by chloramine forming cyanogen chloride. The amount of cyanogen chloride that formed increased as the pH was lowered (Kanno et al., 1982).
At influent concentrations (pH 3.0) of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 250, 140, 79, and 44 mg/g, respectively. At pHs 7.0 and 9.0, the GAC adsorption capacities were 360, 160, 75, and 34 mg/g at influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, respectively (Dobbs and Cohen, 1980).

white or rose needle crystal, in the air in the color can gradually became brown or purple, smelly. Melting point 50 ℃, freezing point 45.4 ℃ (industrial), boiling point 301 ℃, relative density 1.123 (25 ℃), the flash point of 157 ℃. Slightly soluble in water, soluble in ethanol and aether. Can the sublimation, with the steam evaporation.

Sublime the amine at 120o in a stream of nitrogen, then crystallise it from pet ether (b 60-80o), or absolute EtOH then diethyl ether. Dry it in vacuo in an Abderhalden pistol. It has also been purified by crystallisation of its hydrochloride (see below) from water, followed by liberation of the free base and distillation; it is finally purified by zone melting. The styphnate has m 181-182o (from EtOH). [Beilstein 12 III 2846, 12 IV 3009.] CARCINOGEN.