Product
Supplier
Encyclopedia
Inquiry
Home > Encyclopedia > 2-Naphthol

2-Naphthol

pharmaceutical raw materials
2-Naphthol structure

2-Naphthol 

structure
  • CAS No:

    135-19-3

  • Formula:

    C10H8O

  • Chemical Name:

    2-Naphthol

  • Synonyms:

    2-Naphthalenol;2-Naphthol;C.I. 37500;Azogen Developer A;C.I. Azoic Coupling Component 1;C.I. Developer 5;Developer A;Developer AMS;Developer BN;Developer NA;β-Hydroxynaphthalene;Isonaphthol;2-Hydroxynaphthalene;Naphthol B;β-Naphthol;Betanaphthol;β-Naphthyl alcohol;NSC 2044;NSC 5737;Bordeaux Base GP;860440-31-9

  • Categories:

    Cosmetic Ingredient  >  Perfuming

Description

2-Naphthol is a metabolite of naphthalene, catalyzed by cytochrome P450 (CYP) isozymes (CYP 1A1, CYP 1A2, CYP 2A1, CYP 2E1 and CYP 2F2).

2-Naphthol Basic Attributes

144.17000

144.17

205-182-7

P2Z71CIK5H

0719

758883|2044

3077

DTXSID5027061

White, lustrious, bulky leaflets or white powder. Darkens with age

2907151000

Characteristics

20.23000

2.7

DryPowder; Liquid

1.28 g/cm3 @ Temp: 20 °C

121.6 °C

285 °C

160ºC

1.548

H2O: 1 g/L (20 ºC)

Keep away from heat, sparks, and flame. Keep away from sources of ignition. Do not store in direct sunlight. Keep container clos

10 mm Hg ( 145.5 °C)

4.97 (vs air)

Faint phenol-like odor

1.70e-10 cm3/molecule*sec

2.74e-08 atm-m3/mole|Henry's Law constant = 2.74X10-8 atm-cu m/mol at 25 °C

pKa = 9.51 at 25 °C

Hydroxyl radical reaction rate constant= 1.70X10-10 cu cm/molec-sec at 25 °C

550 °C

Dust explosion possible if in powder or granular form, mixed with air.

Safety Information

III

9

UN 3077 9

2

R20/22; R50

S24/25-S61

QL2975000

Xn

Store in an area without drain or sewer access.

Stable. Combustible. Dust may form explosive mixture with air. Incompatible with strong oxidizing agents, phenol.

P273

H302 + H332-H400

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.|Mix with flammable solvent and atomize into an incinerator.|Waste treatment methods. Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contact a licensed professional waste disposal service to dispose of this material. Contaminated packaging: Dispose of as unused product.

Incompatible with antipyrine, camphor, phenol, ferric salts, menthol, potassium permanganate and other oxidizing materials, urethane.|Incompatibilities: Oxidizers, iron salts, 2,3-dimethyl-1-phenyl-3-pyrazolin-5-one (antipyrine), camphor, phenol, menthol, urethane.|Incompatible materials: Strong oxidizing agents, strong bases.

Combustible. Finely dispersed particles form explosive mixtures in air.

|Warning|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P273, P301+P312, P304+P312, P304+P340, P312, P330, P391, and P501|H302+H332 (45.31%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]|P261, P264, P270, P271, P272, P273, P280, P301+P312, P302+P352, P304+P312, P304+P340, P312, P321, P330, P333+P313, P363, P391, and P501|Aggregated GHS information provided by 1013 companies from 11 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|P261, P264, P270, P271, P273, P280, P301+P312, P304+P312, P304+P340, P305+P351+P338, P312, P330, P337+P313, P391, and P501|Danger|P260, P261, P264, P270, P271, P272, P280, P301+P312, P302+P352, P304+P312, P304+P340, P305+P351+P338, P309+P311, P312, P314, P321, P330, P333+P313, P337+P313, P363, P405, and P501

Eye/face protection: Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).|Skin protection: Handle with gloves.|Body Protection: Complete suit protecting against chemicals, The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.|Respiratory protection: For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).

Flammability potential is slight.

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.|Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.

Combustible when exposed to heat or flame.

Accidental Release Measures. Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Discharge into the environment must be avoided. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal.

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.|Precautions for safe handling: Avoid contact with skin and eyes. Avoid formation of dust and aerosols. Provide appropriate exhaust ventilation at places where dust is formed.|Appropriate engineering controls: Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and at the end of workday.|Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.

A skin and eye irritant.|Irritates skin and eyes.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into covered containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment.

Store in an area without drain or sewer access.

A harmful concentration of airborne particles can be reached quickly when dispersed.

The substance is severely irritating to the eyes.

Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the kidneys, blood and eyes. This may result in kidney impairment, anaemia and lens opacities.

NO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.

PREVENT DISPERSION OF DUST!

Use local exhaust or breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles or eye protection in combination with breathing protection if powder.

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. 2-naphthol is produced, as an intermediate or a final product, by process units covered under this subpart.

| 0 - Materials that, under emergency conditions, would offer no hazard beyond that of ordinary combustible materials.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

2-Naphthol was detected in the effluents of timber products industry at 559 ng/uL extract and in the effluent of printing and publishing industries at 56 ng/uL extract(1). 2-Naphthol was also detected, not quantified in wastewater from the textile industry(2).|2-Naphthol was detected in the emissions from the combustion of scrap tires in a horizontal laboratory scale reactor at 650, 750 and 850 degrees Celsius at yields of 200, 79 and 6 mg/kg scrap tire, respectively(1). 2-Naphthol was detected in the emissions of a woodheater at 5.77 mg/kg dry wood burned with fully open airflow, 18 mg/kg dry wood burned with half-closed airflow, and 9.58 mg/kg dry wood burned with closed airflow in a S1 heater; 2-naphthol was also detected at 2.51, 5.68 and 10.7 mg/kg wood burned with an open, halfway closed and closed airflow, respectively, in a S2 heater(2).

SOIL: 2-Naphthol was detected in Mainz and Berlin soils at 1.2 and 24 ng/g(1). 2-Naphthol was also detected in creosote contaminated soil at concentrations ranging from 1.1-5.5 mg/L(2).

Toxicity

IDENTIFICATION AND USE: 2- Naphthol is a white, bulky leaflets or white powder with faint phenol-like odor. The principal uses for 2-naphthol are in the dyes and pigments industries, eg, as a coupling component for azo dyes, and to make important intermediates, such as 3-hydroxy-2-naphthalenecarboxylic acid (BON) and its anilide (naphthol AS), 2-naphtholsulfonic acids, aminonaphtholsulfonic acids, and 1-nitroso-2-naphthol. The major pharmaceutical products based on 2-naphthol are the antifungal tolnaftate, produced by reaction with thiophosgene and N-methyl-m-toluidine; the semisynthetic penicillin nafcillin, produced via 2-ethoxynaphthalene; and the anti-inflammatory naproxen, produced via 2-methoxynaphthalene. It is also was used as a counterirritant in alopecia, also as an anthelmintic, and as an antiseptic in treatment of scabies. HUMAN EXPOSURE AND TOXICITY: The extensive application of 2-naphthol ointments has been responsible for systemic side effects, including vomiting and death. Ingestion can produce renal damage, vomiting, diarrhea, abdominal pain, syncope, convulsions, and hemolytic anemia. Twenty patients who were treated for scabies by rubbing 50 g of a salve containing 7.5% 2-naphthol over the whole body morning and evening for 2 days were reported to have developed hyperemia of the fundus and many had very small white and pigmented spots in the retina. Vitreous opacities were noticed in two cases. Only in one case was abnormality of the lens observed, and this was only a dot in the posterior cortex. Visual acuity was reported to be impaired in two cases, but neither of these had normal eyes before the treatment. ANIMAL STUDIES: Experimentally in rabbits the most consistent ocular change induced by admin 2-naphthol either by stomach or by application to the skin was a development in the retina of small white shiny flecks which soon became pigmented. These became more numerous and increased in size as daily admin of the chemical continued. The retinal vessels and the iris commonly became hyperemic. The aqueous was sometimes slightly turbid, and the vitreous commonly became turbid early, but then cleared despite continuing admin of naphthol. The cornea and conjunctiva were never involved. The other study reported that in the retinas of poisoned adult rabbits spotty degeneration of the rods and cones and irregular variation in the amt of pigment in the pigment epithelium were observed. Vacuoles were present in the nuclear and nerve fiber layer and the ciliary epithelium. When 2-naphthol was administered to pregnant rabbits, the offspring had congenital cataracts, degeneration of the neuroepithelium, and hypertrophy of the retinal pigment cells. An in vivo study was conducted of the biochemical pathways modulating the cataractogenicity of naphthalene. Male mice were treated with naphthalene or its metabolites and with various chemical probes that modulate critical biochemical pathways relevant to naphthalene bioactivation and detoxification. No cataractogenic or lethal effects from 2-naphthol were noted at dose levels of 56 or 100 mg/kg; however doses of 177 and 562 mg/kg killed all the animals within 1.5 hr. ECOTOXICITY STUDIES: As test systems, fish embryos and larvae were the most sensitive, juvenile fathead minnows and arthropods had intermediate sensitivity and algae and snails were the most resistant to the test compounds.

LD50 Mouse ip 97,500 mg/kg|LD50 Rat oral 1960 mg/kg

/AQUATIC SPECIES/ Structure-toxicity relationships were investigated for six organic contaminants, representative of three chemical classes, likely to be found in coal conversion process waters and effluents. Using embryo-larval stages of the rainbow trout (Salmo gairdneri) and largemouth bass (Micropterus salmoides), continuous-flow toxicity tests were performed on hydroxylated aromatic hydrocarbons (phenol, beta-naphthol), azaarenes (quinoline, acridine), and polycyclic aromatic hydrocarbons (naphthalene, phenanthrene). Exposure was initiated at fertilization and maintained through 4 days post-hatching. Median lethal concentrations (LC50), based on combined frequencies of embryo-larval mortality and teratogenesis, were used to rank the toxicity of the compounds to each fish species. With the trout, the order of decreasing toxicity was phenanthrene (0.04 mg/L), beta-naphthol (0.07 mg/L), naphthalene (0.11 mg/L), phenol (0.15 mg/L), acridine (0.32 mg/L) and quinoline (11.0 mg/L). The toxicological ranking with the bass was phenanthrene (0.18 mg/L), naphthalene (0.51 mg/L), acridine (1.02 mg/L), beta-naphthol (1.77 mg/L), phenol (2.80 mg/L) and quinoline (7.50 mg/L). For each class of compounds, the chemical with the greater number of aromatic rings always exerted the greater toxicity. In tests with both fish species, beta-naphthol (two rings) was about twice as toxic as phenol (one ring), and phenanthrene (three rings) was nearly three times more toxic than naphthalene (two rings). Acridine (three rings) was seven times more toxic to bass and 34 times more toxic to trout than was quinoline (two rings). This relationship between ring number and toxicity was in excellent agreement with results from acute tests on the same compounds. Furthermore, a close correlation existed between toxicity and n-octanol:water partition coefficients within each class of compounds.|/AQUATIC SPECIES/ In acute toxicity tests green algae Selenastrum capricornutum, diatoms Nitzschia palea, adult snails Physa gyrina, juvenile cladocerans Daphnia magna, larval midges Chironomus tentans, adult amphipods Gammarus minus, juvenile fathead minnows Pimephales promelas and embryo larva stages of rainbow trout Salmo gairdneri and largemouth bass Micropterus salmoides were exposed for 4 hr (algae), 48 hr (arthropods and snails), 96 hr (fathead minnows), 7 days (largemouth ) bass and 27 days (rainbow trout) to 2 phenols (phenol and beta-naphthol), 2 azaarenes (quinoline and acridine) and 2 polycyclic aromatic hydrocarbons (naphthalene and phenanthrene) present in coal derived oils. LC50 or EC50 (median effective concentrations) ranged from 0.03 mg/L for phenanthrene and rainbow trout to 286.54 mg/L for phenol and the green alga. The rainbow trout embryo larva assay was the most sensitive of the test systems to all the chemicals except quinoline. For this last compound, systems with juvenile fathead minnows and largemouth bass embryos were the more sensitive. As test systems, fish embryos and larvae were the most sensitive, juvenile fathead minnows and arthropods had intermediate sensitivity and algae and snails were the most resistant to the test compounds under the test conditions. Within each chemical class, (phenols, azaarenes and polycyclic aromatic hydrocarbons) toxicity increased with increased ring number except for the reversed relationship with the azaarenes and fathead minnows. beta-Naphthol (2 rings) was 2-45 times more toxic than phenol (1 ring); acridine (3 rings) was 7-27 times more toxic than quinoline (2 rings); and phenanthrene (3 rings) was 3-9 times more toxic than naphthalene (2 rings). There was a relationship between increases in toxicity and increases in the calculated octanol-water partition coefficients of the compounds.

2-Naphthol was detected in the emissions from the hardwoods: red maple (Acer rubrum), red oak (Quercus rubra), paper birch (Betula papyrifera) and the softwoods: white pine (Pinus strobus), hemlock (Tsuga canadensis), balsam fir (Abies balsamae) at concentrations of not detected, 0.135, 0.554, 0.348, 0.217, 0.300 mg/g OC, respectively(1). 2-Naphthol was also detected in the emissions from the hardwood species: Yellow Poplar (Liriodendron tulipifera), White Ash (Fraxinus americana), Sweet-gum (Liquidambar styracilua), Mockernut Hickory (Carya tomentosa), and the softwoods species: Loblolly pine (Pinus taeda) and Slash pine (Pinus elliottii) at concentrations of 0.206, 0.148, 0.173, 0.693, 0.471 and 0.351 mg/g OC, respectively(2).

2-Naphthol's production and use in the dye and pigments industries(1); as an antioxidant for fats, oils, insecticides, a chemical in the synthesis of fungicides, and an antiseptic(2); and in the manufacturing of medicinal organics, dyes and perfumes(3) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a log Kow of 2.7(2) and a regression-derived equation(3), indicates that 2-naphthol is expected to have moderate mobility in soil(SRC). The pKa of 2-naphthol is 9.51(4), indicating that this compound will exist partially in the anion form in the environment and anions do not generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of 2-naphthol from moist soil surfaces is not expected to be an important fate process for the neutral species(SRC) given a Henry's Law constant of 2.74X10-8 atm-cu m/mole(6). Using a Chernozem soil inoculum, 2-naphthol was persistent for more than 30 days(7), indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 390(SRC), determined from a log Kow of 2.7(2) and a regression-derived equation(3), indicates that 2-naphthol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization of the neutral species from water surfaces is not expected(4) based upon a Henry's Law constant of 2.74X10-8 atm-cu m/mole(5). According to a classification scheme(6), an estimated BCF of 28(SRC), from its log Kow and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Utilizing the Japanese MITI test, 68.4% of the Theoretical BOD was reached in 2 weeks(7) indicating that biodegradation is an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-naphthol, which has an extrapolated vapor pressure of 3.2X10-4 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2-naphthol 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 0.17 days(SRC), calculated from its rate constant of 1.70X10-10 cu cm/molecule-sec at 25 °C(3). 2-Naphthol absorbs light at wavelengths >290 nm(4) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2-naphthol with photochemically-produced hydroxyl radicals is 1.70X10-10 cu cm/molecule-sec at 25 °C(1). This corresponds to an atmospheric half-life of about 0.17 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Naphthol is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2-Naphthol absorbs light at wavelengths >290 nm(3) and, therefore, may be susceptible to direct photolysis by sunlight(SRC).

An estimated BCF of 28 was calculated in fish for 2-naphthol(SRC), using a log Kow of 2.7(1) and a regression-derived equation(2). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

The Koc of 2-naphtol is estimated as 390(SRC), using a log Kow of 2.7(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-naphthol is expected to have moderate mobility in soil. The pKa of 2-naphthol is 9.51(4), indicating that this compound will exist partially in the anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5).

The Henry's Law constant for 2-naphthol is as 2.74X10-8 atm-cu m/mole(1). This Henry's Law constant indicates that 2-naphthol is expected to be essentially nonvolatile from water surfaces(2). 2-Naphthol's Henry's Law constant indicates that volatilization from moist soil surfaces for the neutral species may not occur(SRC). 2-Naphthol is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 3.2X10-4 mm Hg(3).

GROUNDWATER: 2-Naphthol was detected in the groundwater in Pensacola, FL at concentrations of 1.66, 0.62, 1.07, and 0.33 mg/L at depths of 6.1, 3.3, 5.8, and 11 meters, respectively(1). 2-Naphthol was detected at a concentration of 50 ug/L in groundwater collected from Holte Gasworks in Denmark(2).

According to the 2012 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 2-naphthol is <10; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 10,985 workers (590 of these were female) were potentially exposed to 2-naphthol in the US(1). Occupational exposure to 2-naphthol may occur through inhalation or other consumer products containing 2-naphthol and dermal contact with this compound at workplaces where 2-naphthol is produced or used. Monitoring data indicate that the general population may be exposed to 2-naphthol via inhalation of wood smoke. Limited data indicate exposure may occur through dermal contact with soil(SRC).

2-Naphthol was detected in the urine of fish consumers at concentrations of 4.4, 1.6 and 5.1 ppb from fish from Lake Michigan, Lake Huron, and Lake Erie, respectively(1). 2-Naphthol was detected with 1-naphthol at a concentration of 0.72 ug/L in amniotic fluid(2). 2-Naphthol was detected at a mean concentration of 7.85 ppb in urine collected from adults in the United States(3).

Drug Information

2-Naphthol ... has had medical uses as a counterirritant in alopecia, also as an anthelmintic, and as an antiseptic in treatment of scabies.

2-Naphthol-containing pastes should be applied only for short periods of time and to a limited area not exceeding 150 square cm.

Between 5 and 10% of a cutaneous dose /of 2-naphthol/ has been recovered from the urine ... .

Several pathways of drug metabolizing enzyme activity were measured in hepatic fractions of cattle, sheep, goats, chickens, turkeys, ducks, rabbits and rats. The pathways examined included the O-demethylation of p-nitrophenol, microsomal ester hydrolysis of procaine and glucuronidation of p-nitrophenol, and the cytosolic acetylation of sulfamethazine and sulfation of 2-naphthol. For most enzymatic pathways measured, goats were more similar to sheep (wether) than to cattle (steers). The exception was UDP-glucuronyltransferase activity, which was significantly higher for the goat than for any other species studied. Within the avian subset, the chicken and turkey were usually the most similar species. The activities of arylsulfotransferase isozymes III and IV were particularly low for the duck compared to the chicken and turkey. N-acetyltransferase activity was very high for rabbits and very low for sheep and goats.|Several pathways of drug metabolizing enzymic activity were measured in hepatic fractions of the channel catfish and rat using model substrates. The pathways examined included the O-demethylation of p-nitroanisole, microsomal ester hydrolysis of procaine and glucuronidation of p-nitrophenol and the cytosolic acetylation of sulfamethazine and sulfation of 2-naphthol. Catfish liver preparations were incubated at both 25 °C and 37 °C. The oxidative metabolism of p-nitrophenol was only 1/8 of that of the rat at 37 °C and 1/12 that of the rat at 25 °C. Procaine ester hydrolysis was negligible in catfish microsomal preparations. At 37 °C, p-nitrophenol glucuronidation was equivalent in catfish and rat microsomes. Catfish cytosolic preparations exhibited N-acetyltransferase and arylsulfotransferase nearly comparable to those of the rat. Rates of glucuronidation and sulfation were higher at 37 °C than at 25 °C in hepatic fractions of the catfish.|To characterize the substrate specificities of various isozymes of carboxylesterases, a series of carbonates, thiocarbonates, carbamates, and carboxylic acid esters containing alpha- or beta-naphthol or p-nitrophenol as leaving groups were tested as substrates of human, rat and mouse liver microsomal esterases; hydrolases A and B from rat liver microsomes were also tested. The carbonates, thiocarbonates, and carboxylic esters of alpha-naphthol were cleaved more rapidly than the corresponding beta-naphthol isomers by the mammalian liver esterases. The majority of the substrates was consistently hydrolyzed at higher rates by hydrolase B compared with hydrolase A. Compared with the corresponding carboxylates, the carbonate moiety of alpha- and beta-naphthol and p-nitrophenol lowered the specific activities of the enzymes by about 5 fold but improved stability under basic conditions. Human and mouse liver microsomal esterase activities were 5 orders of magnitude lower than the esterase activities of hydrolase B. The functional group and lipophilicity of the substrate structure influenced the activity of mammalian esterases.|The inhibition of hydroxysteroid-sulfotransferase (ST) activity in the rat liver by alkylamines was investigated. Liver homogenates were prepared from Wistar rats, and cytosolic fractions were obtained. ST activities towards dehydroepiandrosterone (DHEA), androsterone (AS), and 2-naphthol (2NA) were assayed. Cytosolic fractions were fractionated by column chromatography. Triethylamine, which was used as an elution solvent for column chromatography to purify chemically synthesized 3-phosphoadenosine-5-phosphosulfate (PAPS) inhibited androgen sulfation with AS and DHEA, but did not affect ST activities with cortisol and 2-NA. The sulfate donor ability of various PAPS preparations were compared. Fourteen primary, secondary, and tertiary amines were examined for inhibitory actions on ST activities towards DHEA, cortisol, and 2-NA. A secondary amine, di-n-butylamine, and three tertiary amines, triethylamine, tri-n-propylamine and tri-n-butylamine, inhibited DHEA ST activity by 40 to 60%, irrespective of sex. However, 2-NA and cortisol ST activities were not affected to any significant extent. Lineweaver Burk plots with partially purified hydroxysteroid ST indicated that the inhibition by triethylamine fitted a noncompetitive inhibition. The /results/ conclude that glucocorticoid ST appears to be distinct from the hydroxysteroid ST, and that this has implications for the inhibition of human liver ST activities by synthetic steroids and tertiary amines given as drugs.|For more Metabolism/Metabolites (Complete) data for 2-NAPHTHOL (8 total), please visit the HSDB record page.|2-Naphthol is a known human metabolite of naphthalene.

Fresh air, rest.


Rinse and then wash skin with water and soap.


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

Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand-valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Phenols and related compounds/|Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Administer activated charcoal ... . Dilution may be contraindicated because if may increase absorption. Do not use emetics. Cover skin burns with dry, sterile dressings after decontamination ... . Maintain body temperature. /Phenols and related compounds/|Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Consider vasopressors if patient is hypotensive with a normal fluid volume. Watch for signs of fluid overload ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... Treat seizures with diazepam or lorazepam. ... Use proparacaine hydrochloride to assist eye irrigation ... . /Phenols and related compounds/

/HUMAN EXPOSURE STUDIES/ ... The study aim was to assess naphthalene exposure in pregnant women from Canada, using air measurements and biomarkers of exposure. Pregnant women residing in Ottawa, Ontario completed personal and indoor air sampling, and questionnaires. During pregnancy, pooled urine voids were collected over two 24-hour periods on a weekday and a weekend day. At 2-3 months post-birth, they provided a spot urine sample and a breast milk sample following the 24-hour air monitoring. Urines were analyzed for 1-naphthol and 2-naphthol and breast milk for naphthalene. Simple linear regression models examined associations between known naphthalene sources, air and biomarker samples. Study recruitment rate was 11.2% resulting in 80 eligible women being included. Weekday and weekend samples were highly correlated for both personal (r=0.83, p<0.0001) and indoor air naphthalene (r=0.91, p<0.0001). Urine specific gravity (SG)-adjusted 2-naphthol concentrations collected on weekdays and weekends (r=0.78, p<0.001), and between pregnancy and postpartum samples (r=0.54, p<0.001) were correlated. Indoor and personal air naphthalene concentrations were significantly higher post-birth than during pregnancy (p<0.0001 for signed rank tests); concurrent urine samples were not significantly different. Naphthalene in breast milk was associated with urinary 1-naphthol: a 10% increase in 1-naphthol was associated with a 1.6% increase in breast milk naphthalene (95% CI: 0.2%-3.1%). No significant associations were observed between naphthalene sources reported in self-administered questionnaires and the air or biomarker concentrations. Median urinary concentrations of naphthalene metabolites tended to be similar to (1-naphthol) or lower (2-naphthol) than those reported in a Canadian survey of women of reproductive age. Only urinary 1-naphthol and naphthalene in breast milk were associated. Potential reasons for the lack of other associations include a lack of sources, varying biotransformation rates and behavioral differences over time.|/SIGNS AND SYMPTOMS/ The extensive application of 2-naphthol ointments has been responsible for systemic side effects, including vomiting and death. ...|/SIGNS AND SYMPTOMS/ Ingestion can produce renal damage, vomiting, diarrhea, abdominal pain, syncope, convulsions, and hemolytic anemia.|/CASE REPORTS/ A forty-year-old man treated with 3% 2-naphthol salve for eczema of the neck and face developed irritation of the eyes, and about a half year later was found to have opacities of the posterior cortex of both lenses.|For more Human Toxicity Excerpts (Complete) data for 2-NAPHTHOL (7 total), please visit the HSDB record page.

2-hydroxynaphthalene

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

Cough. Sore throat.


Redness. Pain. Blurred vision.

2-Naphthol Use and Manufacturing

Methods of Manufacturing

2-Naphthol is produced by caustic fusion of naphthalene-2-sulfonic acid. Typically, the sodium salt of the sulfonic acid is added gradually to 50% sodium hydroxide liquor at 300 °C; the melt is then heated further at 320 °C in a gas-fired iron vessel with vigorous agitation. After completion of the reaction, the melt is run into excess water, possibly including filtrate from the previous batch at a proven tolerable level, and the naphtholate solution is neutralized to pH 8 with dilute sulfuric acid. If the temperature is maintained at >100 °C during neutralization, the crude product comes out of solution as an oil, which is separated, washed with hot water, and distilled under vacuum to give pure 2-naphthol. The molten material is processed through a flaker to give the final product for packaging. The fusion yield is about 80% of the theoretical value, resulting in an overall yield of 70% based on naphthalene.|... Alkylation and isomerization are carried out up to 240 °C with a phosphoric acid catalyst. Final catalytic oxidation at 90 - 110 °C gives the hydroperoxide, which is cleaved with dilute sulfuric acid to give 2-naphthol in high overall yield in spite of modest oxidation conversion.|By fusing sodium beta-naphthalene sulfonate with caustic soda. Product is distilled in vacuo and then sublimed.

Uses

2-Naphthol, a compound of great importance in the field of chemistry, is the product of a series of metabolic processes in living organisms, mainly catalyzed by isozymes of the cytochrome P450 family, such as CYP 1A1, CYP 1A2, CYP 2A1, CYP 2E1, and CYP 2F2. This compound exists in the form of dry powder or liquid/solid, with a crystalline appearance ranging from white to pale yellow, emitting a unique odor, which is a distinctive chemical characteristic. The structural feature of 2-naphthol lies in its naphthol structure with a hydroxyl group at the 2nd position, which endows it with a series of biological activities. It is recognized as an antinematode agent, exerting inhibitory effects on nematodes, while its chemical properties also make it considered a genetically toxic substance, potentially affecting genetic material. Furthermore, 2-naphthol is an exogenous metabolite of humans and mice, commonly found in human urine, showing its metabolic pathway in the body. It also possesses the characteristic of a free radical scavenger, possibly participating in the body's antioxidant mechanism. In terms of physical and chemical properties, the density of 2-naphthol is 1.28 g/cm³ at 20°C, its melting point is 121.6°C, and its boiling point is 285°C, with a certain degree of volatility. Its flash point is 160°C, indicating the risk of fire or explosion in high-temperature environments. Its refractive index is 1.548, and its water solubility is extremely low, only able to dissolve in water at extremely low concentrations (1 g/L, 20°C). These characteristics are crucial for safe handling in laboratories and industrial production. When storing and handling 2-naphthol, strict adherence to safety regulations must be followed. It should be stored away from heat sources, sparks, and flames, and should be avoided in contact with open flames. At the same time, it should be stored away from direct sunlight to prevent it from degrading due to photochemical reactions. Keeping the container closed can prevent evaporation and reaction with oxygen in the air. The vapor pressure of 2-naphthol is 10 mm Hg (145.5°C) and its vapor density is 4.97 (relative to air), indicating that it may form flammable vapors under certain conditions. It has a weak phenolic odor and may irritate the respiratory system. Additionally, its hydroxyl radical reaction rate constant and autoignition temperature, among other parameters, reveal the chemical reactions it may participate in under certain conditions, suggesting that extra care is needed when handling and using it. In experimental operations, appropriate personal protective equipment such as chemical protective goggles, respiratory protection devices, and chemical protective gloves should be used to prevent skin contact and inhalation of its vapors. If accidental inhalation occurs, personnel should be immediately moved to fresh air and seek medical assistance. After skin contact, immediate rinsing with plenty of water should be done and medical attention sought promptly. Additionally, 2-naphthol may also contaminate the environment, so any spills or waste should be disposed of according to local regulations and not discarded carelessly. In analysis and synthesis work, special sealed equipment is typically used for operation to reduce exposure and prevent leaks. In cases where heating is required, a water bath or oil bath should be used, avoiding direct flame heating to reduce the risk of fire or explosion. At the same time, its solutions should be stored in a dark place to slow down its possible photochemical reactions. The solubility of 2-naphthol is higher in organic solvents such as alcohol, ketone, and ether, which makes it have certain application value in organic synthesis. However, these characteristics also increase the risk of forming a mixture of solvent vapors during handling, so it should be carried out in a well-ventilated environment and with good ventilation facilities. Understanding these properties of 2-naphthol is crucial in research and industrial production, not only for the safety of experimental personnel but also for the quality of products and environmental protection. Therefore, it is necessary to have a thorough understanding of the properties of 2-naphthol and strictly follow safety operating procedures before conducting related work.

Production

1,000,000 - 10,000,000 lb|2-Naphthalenol is listed as a High Production Volume (HPV) chemical (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).|Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: 2-Naphthalenol. Aggregated National Production Volume: 1 to < 10 million pounds.|Non-confidential 2012 Chemical Data Reporting (CDR) information on the production and use of chemicals manufactured or imported into the United States. Chemical: 2-Naphthalenol. National Production Volume: 1,000,000 - 10,000,000 lb/yr.

Grade: Technical, sublimed, resublimed

Synthetic dye and pigment manufacturing|2-Naphthalenol: ACTIVE

Enzyme linked immunosorbent assay for the specific detection of the mercapturic acid metabolites of naphthalene.

Computed Properties

Molecular Weight:144.17
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:144.057514874
Monoisotopic Mass:144.057514874
Topological Polar Surface Area:20.2
Heavy Atom Count:11
Complexity:133
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Price Analysis

Make your 2-Naphthol purchase based on the price and market insights! ECHEMI provides professional market insights with prices for you to make a better choice. Learn more on 2-Naphthol prices .

Drug Function and Efficacy

Antiseptic and antipruritic effects

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Recommended Suppliers of 2-Naphthol

Scan the QR Code to Share

Feedback & Suggestions
Send Message

Thank you for your feedback. If you require further assistance, please contact us by email at info@echemi.com or call us at +86-532-55729510.