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1-Naphthylamine

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1-Naphthylamine Basic information

Product Name:
1-Naphthylamine
Synonyms:
  • 1-Naphthylamine,1-Aminonaphthalene
  • 1-Aminonaftalen
  • 1-aminonaftalen(czech)
  • 1-Naftilamina
  • 1-Naftylamin
  • 1-Naftylamine
  • 1-Naphthalamine
  • 1-Naphthalenamine
CAS:
134-32-7
MF:
C10H9N
MW:
143.19
EINECS:
205-138-7
Product Categories:
  • -
  • Fluorescent
  • Intermediates of Dyes and Pigments
  • Anilines, Aromatic Amines and Nitro Compounds
  • Chemistry
  • Amines
  • Aromatics
  • Intermediates
  • Building Blocks
  • C10
  • Chemical Synthesis
  • Nitrogen Compounds
  • Organic Building Blocks
Mol File:
134-32-7.mol
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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
pka
3.92(at 25℃)
form 
flakes
color 
light tan to purple
PH
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
Merck 
14,6398
BRN 
386133
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
1-Naphthalenamine(134-32-7)
EPA Substance Registry System
1-Naphthalenamine(134-32-7)
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Safety Information

Hazard Codes 
C,N,Xn,T
Risk Statements 
34-51/53-22-45
Safety Statements 
26-36/37/39-45-61-24-53
RIDADR 
UN 2790 8/PG 3
WGK Germany 
2
RTECS 
QM1400000
8-23
Autoignition Temperature
460 °C
HS Code 
2921 45 00
HazardClass 
6.1(b)
PackingGroup 
III
Hazardous Substances Data
134-32-7(Hazardous Substances Data)
Toxicity
LD50 orally in Rabbit: 680 mg/kg

MSDS

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1-Naphthylamine Usage And Synthesis

Chemical Properties

Solid

Chemical Properties

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

Physical properties

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).

Uses

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

Uses

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

General Description

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].

Reactivity Profile

1-Aminonaphthalene is incompatible with oxidizing agents. 1-Aminonaphthalene is also incompatible with nitrous acid. 1-Aminonaphthalene reduces warm ammoniacal silver nitrate. .

Hazard

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

Health Hazard

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.

Health Hazard

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.

Fire Hazard

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

Safety Profile

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.

Potential Exposure

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.

Environmental Fate

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).

Shipping

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

Purification Methods

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.

Incompatibilities

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.

Waste Disposal

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.

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