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1-Naphthylamine

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1-Naphthylamine Basic information
1-Naphthylamine Chemical Properties
  • Melting point:47-50 °C(lit.)
  • Boiling point:301 °C(lit.)
  • Density 1.114 g/mL at 25 °C(lit.)
  • vapor pressure 0.003 hPa (20 °C)
  • refractive index 1.6703
  • Flash point:>230 °F
  • storage temp. 2-8°C
  • solubility 1.7g/l
  • form flakes
  • pka3.92(at 25℃)
  • color light tan to purple
  • OdorAmmonia odor
  • PH7.1 (1g/l, H2O, 20℃)
  • PH RangeNon& uorescence (3.4) to blue & uorescence (4.8)
  • Water Solubility Insoluble. 0.1698 g/100 mL
  • Merck 14,6398
  • BRN 386133
  • Henry's Law Constant6.13 x 10-10 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
  • Exposure limitsTLV-TWA not assigned; carcinogenicity: Human Carcinogen (skin) (MSHA and OSHA).
  • Major Applicationcolor filter, photoresists, recording media, light-emitting device, disk, display device, oil products, construction materials, leather, textile, chalk, explosives
  • CAS DataBase Reference134-32-7(CAS DataBase Reference)
  • IARC3 (Vol. 4, Sup 7) 1987
  • NIST Chemistry Reference1-Naphthalenamine(134-32-7)
  • EPA Substance Registry System1-Naphthalenamine (134-32-7)
Safety Information
MSDS
1-Naphthylamine Usage And Synthesis
  • Chemical PropertiesSolid
  • Chemical Propertiesα-Naphthylamine exists as white needle-like crystals which turn red on exposure to air. Has a weak ammonia-like odor.
  • Physical propertiesWhite 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).
  • Uses1-Naphthylamine is used in the manufactureof dyes and tonic prints.
  • UsesA reagent used to synthesize various dyes used in the textile industry.
  • Production MethodsThere 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.
  • Synthesis Reference(s)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
  • General DescriptionA 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.
  • Air & Water ReactionsSensitive 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].
  • Reactivity Profile1-Aminonaphthalene is incompatible with oxidizing agents. 1-Aminonaphthalene is also incompatible with nitrous acid. 1-Aminonaphthalene reduces warm ammoniacal silver nitrate. .
  • HazardToxic, especially if containing the β isomer; a questionable carcinogen.
  • Health HazardInhalation 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.
  • Health Hazard1-Naphthylamine is a moderately toxicand cancer-causing substance. The toxicsymptoms arising from oral intake orskin absorption of this compound includeacute hemorrhagic cystitis, dyspnea, ataxia,dysuria, and hematuria. An intraperitonealLD50 value in mice is 96 mg/kg. Inhalationof dusts or vapors is hazardous, showingsimilar symptoms. 1-Naphthylamine causedleukemia in rats. There is substantialevidence of its cancer-causing effects inanimals and humans.
  • Fire HazardSpecial Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire.
  • Safety ProfileConfirmed carcinogen with experimental tumorigenic data. Along with p-naphthylamine and benzidine, it has been incriminated as a cause of urinary bladder cancer. Poison by subcutaneous and intraperitoneal routes. Moderately toxic by ingestion. Mutation data reported. Combustible when exposed to heat or flame. Incompatible with nitrous acid. To fight fire, use dry chemical, CO2, mist, spray. When heated to decomposition it emits toxic fumes of NOx.
  • Potential Exposureα-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.
  • Carcinogenicity1-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.
  • Environmental FateBiological. 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).
  • ShippingUN2077 alpha-Naphthylamine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. PGIII.
  • Purification MethodsSublime 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.
  • IncompatibilitiesIncompatible 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.
  • Waste DisposalControlled 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.
1-Naphthylamine Preparation Products And Raw materials
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