| Chemical Abstract Number (CAS #) |
134327
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| Synonyms | alpha-Naphthylamine |
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1-Naphthylamine |
| Analytical Methods |
EPA Method 625 |
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EPA Method 8250A |
| Molecular Formula | C10H9N |
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| Use | TONING PRINTS MADE WITH CERIUM SALTS.
CHEM INT FOR DYES, EG, AZOIC DIAZO COMPONENT; CHEM INT FOR AZO DYE
COUPLING AGENTS, FOR N-1-NAPHTHYLPHTHALMIC ACID HERBICIDE, FOR
N-PHENYL-1-NAPHTHYLAMINE RUBBER ANTIOXIDANT, FOR AN IMIDAZOLINE
ADRENERGIC AGENT; CHEM INT FOR 1-NAPHTHYLTHIOUREA RODENTICIDE &
FOR A FLUOROACETAMIDE MITICIDE (FORMER USES).
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| Apparent Color | NEEDLES FROM DIL ETHANOL AND ETHER ; YELLOW RHOMBIC NEEDLES ;
WHITE CRYSTALS ; NEEDLES, BECOME RED ON EXPOSURE TO AIR OR A REDDISH,
CRYSTALLINE MASS
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| Odor | WEAK AMMONIA-LIKE ODOR
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| Boiling Point | 300.8 DEG C @ 760 MM HG
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| Melting Point | 50 DEG C
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| Molecular Weight | 143.18
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| Density | SP GR: 1.1229 @ 25 DEG C/25 DEG C
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| Sensitivity Data | Eye: immediately irritating.
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| Environmental Impact | 1-Naphthylamine may be released to the environment in waste streams and effluents from
coal tar, coal gasification and shale oil facilities, in effluents from its use in the synthesis of dyes
and herbicides, by the degradation of the herbicide naptalam, and by the combustion of fuels
containing a high nitrogen content. If released to soil, microbial metabolism is expected to be the
primary mechanism for the degradation of 1-naphthylamine. Adsorption of 1-naphthylamine in soil
involves a rapid and reversible equilibrium followed by a slow reaction of covalent binding to the
humic fraction of soil which is not readily reversible. Experimental Koc values of 2688-3777 have
been determined which indicate only slight mobility in soil, however, the detection of
1-naphthylamine in a groundwater indicates that leaching is possible. The soil half-life of
1-naphthylamine was found to be in excess of one year in laboratory studies; the covalent binding
may explain why it resists decomposition in soil. If released to water, 1-naphthylamine will react
with photochemically produced RO2 radicals with an estimated half-life of 115 hours in sunlit
natural water. Reaction with hydroxyl radicals and direct photolysis may also contribute to its
removal in sunlit natural water. 1-Naphthylamine may covalently bind to humic material in water;
its detection in river sediment indicates that some adsorption does occur. Adsorption to aquatic
humic material may lessen the removal rate due to photochemical mechanisms and significantly
lengthen the persistence time. Hydrolysis, volatilization and bioconcentration are not expected to
be important in water. If released to the atmosphere, 1-naphthylamine will react in the
vapor-phase with photochemically produced hydroxyl radicals at an estimated half-life of 12.7
hours. Since 1-naphthylamine strongly absorbs UV light above 290 nm, direct photolysis is
possible. Occupational exposure may occur through dermal and inhalation routes while general
population exposure may occur through inhalation of mainstream cigarette smoke.
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| Environmental Fate | TERRESTRIAL FATE: Laboratory studies have indicated that microbial metabolism is
the primary mechanism for the degradation of 1-naphthylamine in soil, although the soil half-life
for 1-naphthylamine in these studies was in excess of one year . Adsorption in soil initially
involves a rapid and reversible equilibrium followed by a slow reaction of covalent binding to the
humic fraction of soil. Covalent binding of aromatic amines to soil humic matter, which represents
a conversion of the amine to a latent form, is not readily reversible ; the covalent binding may
explain why 1-naphthylamine resists decomposition in soil . Experimental Koc values of
2688-3777 have been determined which indicate only slight mobility in soil while estimation
equations predict high soil mobility; the difference may be explained by the covalent binding. The
detection of 1-naphthylamine in a groundwater indicates that leaching is possible. Since
1-naphtylamine strongly absorbs UV light above 290 nm, direct photolysis on soil surfaces is
possible.
AQUATIC FATE: When released to water, 1-naphthylamine will react with photochemically
produced RO2 radicals with an estimated half-life of 115 hours in sunlit natural water. Reaction
with hydroxyl radicals in sunlit natural water may also contribute to its removal. Since
1-naphthylamine strongly absorbs UV light above 290 nm, direct photolysis is also possible.
Covalent binding of 1-naphthylamine to the humic fraction of soil suggests that adsorption by
humic matter in water may be important; the detection of 1-naphthylamine in river sediment
indicates that some adsorption does occur. Adsorption to aquatic humic material may lessen the
removal rate due to photochemical mechanisms and significantly lengthen the persistence time.
Hydrolysis, volatilization, and bioconcentration are not expected to be important.
ATMOSPHERIC FATE: 1-Naphthylamine will react in the vapor-phase with photochemically
produced hydroxyl radicals at an estimated half-life of 12.7 hours. Since 1-naphthylamine strongly
absorbs UV light above 290 nm, direct photolysis is possible.
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| Drinking Water Impact | GROUNDWATER: 1-Naphthylamine was qualitatively detected in groundwater beneath
a coal tar distillation and creosote wood preserving facility in St. Louis Park, MN .
SURFACE WATER: 1-Napthylamine has been qualitatively detected in the Buffalo River .
1-Naphthylamine was detected in the Sumida River, Japan, along with benzidine,
dichlorobenzidine and 2-naphthylamine, at combined concentrations of 0.275-0.562 ppm .
EFFL: 1-Naphthylamine was qualitatively found in waste streams at a coal gasification facility in
Chicago . Concentrations of 3 ppm was detected in the process water from an oil shale facility
in Australia .
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