| Identification | More | [Name]
1-Aminonaphthalene | [CAS]
134-32-7 | [Synonyms]
1-AMINONAPHTHALENE
1-NAPHTHYLAMINE
AKOS BBS-00003569
ALPHA-AMINONAPHTHALENE
ALPHA-NAPHTHYLAMINE
ALPHA NAPTHYLAMINE
α-Aminonaphthalene
A-NAPHTHYLAMINE
azoic diazo component 114
Fast garnet B base
naphthalidam
Naphthalidine
α-Naphthylamine
NITRATE REAGENT A
1-Aminonaftalen
1-aminonaftalen(czech)
1-Naftilamina
1-Naftylamin
1-Naftylamine
1-Naphthalamine | [EINECS(EC#)]
205-138-7 | [Molecular Formula]
C10H9N | [MDL Number]
MFCD00004016 | [Molecular Weight]
143.19 | [MOL File]
134-32-7.mol |
| Chemical Properties | Back Directory | [Appearance]
α-Naphthylamine exists as white needle-like
crystals which turn red on exposure to air. Has a weak
ammonia-like odor. | [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 | [Fp ]
>230 °F
| [storage temp. ]
2-8°C
| [solubility ]
1.7g/l | [form ]
flakes
| [pka]
3.92(at 25℃) | [color ]
light tan to purple
| [Odor]
Ammonia odor | [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 ]
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) | [IARC]
3 (Vol. 4, Sup 7) 1987 | [NIST Chemistry Reference]
1-Naphthalenamine(134-32-7) | [Storage Precautions]
Light sensitive;Air sensitive | [EPA Substance Registry System]
134-32-7(EPA Substance) |
| Safety Data | Back Directory | [Hazard Codes ]
C,N,Xn | [Risk Statements ]
R34:Causes burns.
R51/53:Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment .
R22:Harmful if swallowed. | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
S61:Avoid release to the environment. Refer to special instructions safety data sheet .
S24:Avoid contact with skin . | [RIDADR ]
UN 2790 8/PG 3
| [WGK Germany ]
2
| [RTECS ]
QM1400000
| [F ]
8-23 | [Autoignition Temperature]
460 °C | [HazardClass ]
6.1(b) | [PackingGroup ]
III | [HS Code ]
29214500 | [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. | [Hazardous Substances Data]
134-32-7(Hazardous Substances Data) | [Toxicity]
LD50 orally in Rabbit: 680 mg/kg |
| Hazard Information | Back Directory | [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. | [Reactivity Profile]
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. . | [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]. | [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. | [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. | [Fire Hazard]
Special Hazards of Combustion Products: Toxic nitrogen oxides are produced in a fire. | [First aid]
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. | [Shipping]
UN2077 alpha-Naphthylamine, Hazard Class:
6.1; Labels: 6.1-Poisonous materials. PGIII. | [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. | [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. | [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. | [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. | [Application]
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. | [Definition]
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. | [Preparation]
1-Nitronaphthalene reduction. | [Production Methods]
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. | [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 | [Carcinogenicity]
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. | [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). | [Properties and Applications]
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. | [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. |
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