2-Naphthylamine

Nitrogen Compounds -> Naphthylamines

Carcinogens

log Kow =2.28

2.28

2.28

2.4

1.061 at 208 °F (NTP, 1992) - Denser than water; will sink

1.061 @ 98 °C/4 °C

1.061 g/cm³

1.06 at 208 °F

1.65 @ 98°C

(208 °F): 1.06

COLORLESS CRYSTALS WHICH DARKEN IN AIR TO A REDDISH-PURPLE COLOR

White to red crystalls [Note: Darkens in air to reddish-purple color].

less than 1 mg/mL at 72 °F (NTP, 1992)

Soluble in alcohol, ether

SOL IN MANY ORG SOLVENTS

In water, 6.40 mg/L @ 18 °C

0.189 mg/mL at 25 °C

Solubility in water: poor

315 °F (NIOSH, 2024)

157 °C

157 °C

157 °C

315 °F

315 °F

583 °F at 760 mmHg (NTP, 1992)

306 °C, also stated as 294 °C

306 °C

583 °F

306.2 °C @760 [mm Hg]

583 °F

232 to 235 °F (NTP, 1992)

111-113 °C

MP: 109.5 °C /Technical/

113 °C

110.2-113 °C

232 °F

Danger

H302: Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)

Danger

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P318, P330, P391, P405, and P501 (click each P-code to see the statement)

Hazard Traits - Carcinogenicity

Hazard Traits - Carcinogenicity

Restricted substance: 2-naphthylamine

2-Naphthalenamine: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· Combustible material: may burn but does not ignite readily.

· Combustible material: may burn but does not ignite readily.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

· TOXIC and/or CORROSIVE; inhalation, ingestion or skin contact with material may cause severe injury or death.

1650 153

3411 153

1650 153

National Toxicology Program. Eleventh Report on Carcinogens (2005). The Report on Carcinogens is an informational scientific and public health document that identifies and discusses substances (including agents, mixtures, or exposure circumstances) that may pose a carcinogenic hazard to human health. 2-Naphthylamine (91-59-8) is listed as known to be a human carcinogen.[Available from, as of July 31, 2009: http://ntp.niehs.nih.gov/ntp/roc/eleventh/profiles/s117naph.pdf]

U168; As stipulated in 40 CFR 261.33, when beta-naphthylamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, dry powder, foam.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

General First Aid:

General First Aid:

(General first aid procedures)

· Wear positive pressure self-contained breathing apparatus (SCBA).

· Wear positive pressure self-contained breathing apparatus (SCBA).

If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical, or carbon dioxide. Keep run-off water out of sewers and water sources.

/Use:/ Dry powder, foam, water spray.

Separated from food and feedstuffs. Well closed.

Keep well closed and protected from light. /2-Naphthylamine acetate/

PRECAUTIONS FOR "CARCINOGENS": Storage site should be as close as practical to lab in which carcinogens are to be used, so that only small quantities required for ... expt need to be carried. Carcinogens should be kept in only one section of cupboard, an explosion-proof refrigerator or freezer (depending on chemicophysical properties ...) that bears appropriate label. An inventory ... should be kept, showing quantity of carcinogen & date it was acquired ... Facilities for dispensing ... should be contiguous to storage area. /Chemical Carcinogens/

Sweep spilled substance into covered containers. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment.

PRECAUTIONS FOR "CARCINOGENS": A high-efficiency particulate arrestor (HEPA) or charcoal filters can be used to minimize amt of carcinogen in exhausted air ventilated safety cabinets, lab hoods, glove boxes or animal rooms ... Filter housing that is designed so that used filters can be transferred into plastic bag without contaminating maintenance staff is avail commercially. Filters should be placed in plastic bags immediately after removal ... The plastic bag should be sealed immediately ... The sealed bag should be labelled properly ... Waste liquids ... should be placed or collected in proper containers for disposal. The lid should be secured & the bottles properly labelled. Once filled, bottles should be placed in plastic bag, so that outer surface ... is not contaminated ... The plastic bag should also be sealed & labelled. ... Broken glassware ... should be decontaminated by solvent extraction, by chemical destruction, or in specially designed incinerators. /Chemical Carcinogens/

[40 CFR 240-280, 300-306, 702-799 (7/1/2004)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U168, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.

A) Dissolve in such combustible solvent as alcohols, benzene, etc. Spray the soln into a furnace with afterburner and scrubber. B) Pour into a mixture of sand and soda ash (9:1). After mixing, put into a paper carton stuffed full with packing paper to serve as fuel. Burn in a furnace. Recommendable method: Incineration.

PRECAUTIONS FOR "CARCINOGENS": There is no universal method of disposal that has been proved satisfactory for all carcinogenic compounds & specific methods of chem destruction ... published have not been tested on all kinds of carcinogen-containing waste. ... summary of avail methods & recommendations ... /given/ must be treated as guide only. /Chemical Carcinogens/

PRECAUTIONS FOR "CARCINOGENS": ... Incineration may be only feasible method for disposal of contaminated laboratory waste from biological expt. However, not all incinerators are suitable for this purpose. The most efficient type ... is probably the gas-fired type, in which a first-stage combustion with a less than stoichiometric air:fuel ratio is followed by a second stage with excess air. Some ... are designed to accept ... aqueous & organic-solvent solutions, otherwise it is necessary ... to absorb soln onto suitable combustible material, such as sawdust. Alternatively, chem destruction may be used, esp when small quantities ... are to be destroyed in laboratory. /Chemical Carcinogens/

For more Disposal Methods (Complete) data for 2-NAPHTHYLAMINE (8 total), please visit the HSDB record page.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 1,000(2), indicates that 2-naphthylamine is expected to have low mobility in soil(SRC). Results of a batch equilibrium study with various soils indicated that 1-naphthylamine, which is structurally analogous to 2-naphthylamine, binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). Volatilization of 2-naphthylamine from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 8.10X10-8 atm-cu m/mole(5). 2-Naphthylamine is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 2.56X10-4 mm Hg(6). Based on primary soil biodegradation and mineralization studies, 2-naphthylamine is expected to biodegrade slowly in soil(7,8).

AQUATIC FATE: Based on a classification scheme(1), a Koc value of 1,000(2), indicates that 2-naphthylamine is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon a Henry's Law constant of 8.10X10-8 atm-cu m/mole(4). The pKa of 2-naphthylamine is 4.16(5), indicating that this compound will partially exist as a cation in the environment. According to a classification scheme(6), an estimated BCF of 11(SRC), from a log Kow of 2.28(7) and a regression-derived equation(8), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Based on primary soil biodegradation and mineralization studies, 2-naphthylamine is expected to biodegrade slowly in water(9,10).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-naphthylamine, which has a vapor pressure of 2.56X10-4 mm Hg at 25 deg(2) is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-naphthylamine is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 1.9 hours(SRC), calculated from its rate constant of 2.0X10-10 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 2-Naphthylamine was shown to photolyze in direct sunlight with half-lives ranging from 0.05 to 0.19 hours(4).

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

inhalation, skin absorption, ingestion, skin and/or eye contact

Blue lips, fingernails and skin. Confusion. Dizziness. Convulsions. Headache. Nausea. Unconsciousness.

MAY BE ABSORBED! Redness. Further see Inhalation.

See Inhalation.

dermatitis; hemorrhagic cystitis; dyspnea (breathing difficulty); ataxia; methemoglobinemia, hematuria (blood in the urine); dysuria; [potential occupational carcinogen]

2-Naphthylamine was detected in aqueous industrial effluent extracts collected between Nov 1979-81 at a concentration of 9150 ng/ul(1). 2-Naphthylamine was identified at a concentration of 43.6 mg/g in a basic fraction sample of HYGAS low-temperature reactor tar from a HYGAS coal gasification plant in Chicago(2). 2-Naphthylamine was found in the waste streams of the Sumida River, Japan where it has been produced and used and has been reported to be present in the effluent from certain dyestuffs factories(3).

Preplacement and periodic examinations should include an evaluation of exposure to other carcinogens, use of alcohol, smoking, medications, and family history. The general health of exposed persons should also be evaluated in periodic examinations.

Monthly urinalysis of exposed personnel, prostatic alkaline phosphatase (PAP) examinations every 6 months, and cystoscopy should be employed where indicated.

The urine cytology surveillance was found to be useful for two reasons: first, it detected tumors in 5 out of 6 cases surveyed, and second, 4 cases screened had tumors curable by transurethral operation, while other cases underwent cystectomy.

PRECAUTIONS FOR "CARCINOGENS": Whenever medical surveillance is indicated, in particular when exposure to a carcinogen has occurred, ad hoc decisions should be taken concerning ... /cytogenetic and/or other/ tests that might become useful or mandatory. /Chemical Carcinogens/

The measured Koc for 2-naphthylamine is 1,000(1). According to a classification scheme(2), this Koc value suggests that 2-naphthylamine is expected to have low mobility in soil. Results of a batch equilibrium study with various soils indicated that 1-naphthylamine, which is structurally analogous to 2-naphthylamine, binds to soil in two phases with an initial rapid and reversible equilibrium established between the amine and the inorganic and organic components of soil followed subsequently by a strong association with the humic fraction of soil via covalent binding(3,4). Aminonaphthalenes are known to form complexes with soil matter(5). The pKa of 2-naphthylamine is 4.16(6), indicating that this compound will partially exist in cation form in the environment.

U168; As stipulated in 40 CFR 261.33, when beta-naphthylamine, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).

Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 1 lb or 0.454 kg. The toll free number of the NRC is (800) 424-8802; In the Washington D.C. metropolitan area (202) 426-2675. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b).

beta-Naphthylamine (BNA)... is a stimulatory agent of respiratory burst in rat peritoneal macrophages besides being a potent carcinogen. Since polymixin-B and staurosporine are inhibitors of protein-kinase-C (PKC), the data suggest that PKC may be involved in the intracellular signal transduction pathway of BNA stimulated superoxide production.

N-oxidation by cytochrome p450 enzymes is an initial step in the metabolic activation of aromatic amine compounds. Once metabolized, these compounds are converted to DNA-reactive species which can exhibit potent mutagenic and/or carcinogenic activity. The precise mechanism of P450 enzyme oxidation is not completely understood, although various theories, involving either one-electron transfer, two-electron transfer or addition-rearrangement, have been debated. In previous studies, selection of the most probable mechanism has been based on consideration of Huckel theory charge distribution calculations and experimentally-derived enzyme metabolism data. This approach can now be improved by incorporating contemporary, ab initio quantum chemical methods to accurately determine the chemical properties of P450 aromatic amine substrates. ...This work ... compare/ed/ the experimental oxidation yields and rates of 1-naphthylamine (1-NA), 2-naphthylamine (2-NA) and 2-aminofluorene (2-AF). This data was then analyzed with respect to ab initio-calculated charge distributions and energies of reactants, oxidation products and proposed intermediates. ...Analysis of theoretical and experimental data indicates that the one-electron model is more consistent with oxidation rate data for 1-NA, 2-NA, and 2-AF. ...In contrast to earlier studies, the one-electron mechanism is more likely to be the pathway for P450-catalyzed aromatic amine oxidation.

... Beta-naphthylamine ... is transformed into bis(2-amino-1-naphthyl)hydrogen phosphate and excreted ... Its hydrolysis in body to 2-amino-1-naphthol is thought to be responsible for carcinogenic activity ...

... Although metabolite, 2-amino-1-naphthylsulfuric acid is resistant to hydrolysis by urinary arylsulfatase, glucuronide and phosphate conjugates are hydrolyzed in bladder to give free ortho-aminonaphthol.

Incubation of 2-naphthylamine with rat liver microsomes fortified with NADPH resulted in formation of two types of free radicals which were identified as n-hydroxy-2-naphthylamine and 2-amino-1-naphthol. The former radical was oxidized to 2-nitrosonaphthalene radical. Amount of metabolites produced could be increased by using microsomes from phenobarbital induced rats.

In vitro metabolic n-oxidation of 2-naphthylamine investigated with intact dog bladder, whole intact bladder mucosa and microsomes from this tissue. Very low levels of metabolic n-oxidation were detected. No n-oxidation by these tissue preparations was observed using GLC. Concentration of n-oxidized metabolism observed in urine of exposed dogs suggest that n-oxidation takes place predominately in liver and that the bladder plays, at most, a minor role in formation of the presumed proximate urinary carcinogens.

For more Metabolism/Metabolites (Complete) data for 2-NAPHTHYLAMINE (12 total), please visit the HSDB record page.

2-naphthylamine has known human metabolites that include N-Hydroxy-2-naphthalenamine.

It /(2-naphthylamine)/ is readily absorbed through the skin and by inhalation.

A three-compartment pharmacokinetic model was developed with a computer to separate absorption, metabolism and distribution of n-hydroxy-2-naphthylamine in intact animal from events in bladder lumen (deposition, hydrolysis, and resorption). Total bladder exposure to carcinogen, N-hydroxy-2-naphthylamine, was simulated; and urine pH and voiding interval, both of which differ among species, were tested as variables. For humans and dogs, urine ph was found to be more acidic than monkeys or rats; while voiding intervals in rats were shorter than in monkeys, dogs, or humans. Relative species susceptibilities, indicated by model as total bladder exposure to hydroxy metab under conditions of normal urine pH and frequency of micturition for each species were: human greater than or equal to dog greater than monkey greater than rat. This is consistent with reported carcinogenic potency of 2-naphthylamine in these species and suggests that urine pH and voiding interval are important factors in bladder cancer.

2-Naphthylamine metabolism occurs through oxidation to form 2-amino-1-naphthol. At least 10 metabolites of 2-naphthylamine have been identified in the urine of rats and rabbits. In these animals, 70-80% of metabolites are removed with the urine, 20-30% are excreted in the feces.

Rarely used today; used in the past in research and in the production of dyes and rubber; [ACGIH]

Not imported or used in the U.S. since 1975. [ACGIH]

Formerly in manufacture of dyes, as antioxidant in rubber.

Chemical intermediate for dyes /SRP60:Former use/

Chemical intermediate for rubber antioxidants /SRP60:Former use/

Used to produce 2-chloronaphthalene. /SRP60:Former use/

(1978) No Data

(1982) No Data

(1978) No Data

(1982) No Data

(1967): 38,000 pounds

Prepared by heating beta-naphthol with ammonium sulfite and NH4OH at 150 °C.

Reaction of 2-naphthol with ammonia and ammonium sulphite (former method)

... Can be made by the Bucherer reaction starting with 2-naphthalenol.

... No longer commercially produced or used in the United States.

The rodenticide ANTU (alpha-naphthylthiourea) was used in the United Kingdom mainly in the late 1940s and early 1950s. The product /at that time/ contained up to 0.2% of beta-naphthylamine as an impurity, and it was finally withdrawn in 1967 as a suspected carcinogen. Fourteen cases of urothelial tumors among rodent operatives /were/ reported.