1-Naphthylamine Chemical Properties
- Melting point:
- 47-50 °C(lit.)
- Boiling point:
- 301 °C(lit.)
- 1.114 g/mL at 25 °C(lit.)
- vapor pressure
- 0.003 hPa (20 °C)
- refractive index
- Flash point:
- >230 °F
- storage temp.
- 3.92(at 25℃)
- light tan to purple
- 7.1 (1g/l, H2O, 20℃)
- PH Range
- Non& uorescence (3.4) to blue & uorescence (4.8)
- Water Solubility
- Insoluble. 0.1698 g/100 mL
- Henry's Law Constant
- 6.13 x 10-10 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
- Exposure limits
- TLV-TWA not assigned; carcinogenicity: Human Carcinogen (skin) (MSHA and OSHA).
- Major Application
- color filter, photoresists, recording media, light-emitting device, disk, display device, oil products, construction materials, leather, textile, chalk, explosives
- CAS DataBase Reference
- 134-32-7(CAS DataBase Reference)
- NIST Chemistry Reference
- EPA Substance Registry System
- 1-Naphthalenamine (134-32-7)
- Hazard Codes
- Risk Statements
- Safety Statements
- UN 2790 8/PG 3
- WGK Germany
- Autoignition Temperature
- 460 °C
- 2921 45 00
- Hazardous Substances Data
- 134-32-7(Hazardous Substances Data)
- LD50 orally in Rabbit: 680 mg/kg
1-Naphthylamine Usage And Synthesis
α-Naphthylamine exists as white needle-like crystals which turn red on exposure to air. Has a weak ammonia-like odor.
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.
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,
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.
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.
Air & Water Reactions
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].
1-Aminonaphthalene is incompatible with oxidizing agents. 1-Aminonaphthalene is also incompatible with nitrous acid. 1-Aminonaphthalene reduces warm ammoniacal silver nitrate. .
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.
1-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.
Special Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire.
Confirmed 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.
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.
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).
UN2077 alpha-Naphthylamine, Hazard Class: 6.1; Labels: 6.1-Poisonous materials. PGIII.
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.
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.
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.
1-Naphthylamine Preparation Products And Raw materials
- ACID RED 66
- Solvent Red 24
- 1-Naphthyl isothiocyanate
- 4-DIMETHYLAMINO-1-NAPHTHYL ISOTHIOCYANATE
- Acid Green 1
- ACID RED 114
- ACID ALIZARIN VIOLET N
- 1-NITROSO-2-NAPHTHOL-3,6-DISULFONIC ACID DISODIUM SALT
- Sodium 4-amino-1-naphthalenesulfonate
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