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HCID 8663作成日:2026年10月23日

ナフトール

ナフトール · Naphthalenol · Maceni

https://huagongshe.com/ja/chemical/8663

ナフトール の分子構造式

識別子と物理属性

CAS No.1321-67-1
分子式C10H8O
平均分子量144.17 g/mol
単同位体質量144.05751488 g/mol
SMILESOc1ccc2ccccc2c1
InChIKeyJWAZRIHNYRIHIV-UHFFFAOYSA-N
PubChem CID8663
ChEMBLCHEMBL14126
ChEBICHEBI:10432
EC No.205-182-7
DTXSIDDTXSID5027061
現地名ナフトール

化学・物理的性質

XLogP2.7
極性表面積20.2
水素結合供与体数1
水素結合受容体数1
回転可能結合数0
重原子数11
形式電荷0
複雑度133
物質分類Other Classes -> Naphthols
SpringerMaterials Properties13C nuclear magnetic resonance spectrum
LogP(分配係数)log Kow = 2.702.75
臭いFaint phenol-like odor
密度1.28 g/cu cm at 20 °C1.28 g/cm³0.581 @ 0°C1.2170
Color/FormWhite, lustrious, bulky leaflets or white powder. Darkens with age
溶解度In water, 7.55X10+2 mg/L at 25 °CSoluble in alcohol, ether, chloroform, glycerol, oils, alkaline solutionsVery soluble in ethanol, ethyl ethersoluble in benzene, chloroformslightly soluble in ligroin1 gram dissolves in 1000 mL water, 80 mL boiling water, 0.8 mL alcohol, 17 mL chloroform, 1.3 mL ether755 mg/L @ 25 °C (exp)Solubility in water, g/100ml at 25 °C: 0.074
引火点152.7 °C153 °C153 °C (307 °F) (Closed cup)307 °F (153 °C) (Closed cup)
Endocrine DisruptorsPotential endocrine disrupting compound
沸点285 °C285.00 to 286.00 °C. @ 760.00 mm Hg286 °C @760 [mm Hg]390.57°C (rough estimate)
融点121.6 °C123 °C122 °C122.5°C
蒸気密度Relative vapor density (air = 1): 5
屈折率1.7580 (estimate)
EPAの化学物質情報Naphthol (1321-67-1)

安全性と法規制

GHS 分類WarningH302: Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P330, P391, and P501 (click each P-code to see the statement)DangerH302+H332 (55%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oralacute toxicity, inhalation]P261, P264, P264+P265, P270, P271, P272, P273, P280, P301+P317, P302+P352, P304+P340, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P391, and P501 (click each P-code to see the statement)
規制情報Chemical: 2-Naphthalenol2-Naphthalenol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Naphthalenol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 05-07-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/264702-Naphthol: Does not have an individual approval but may be used under an appropriate group standard
その他の安全情報IMAP assessments - 2-Naphthalenol: Human health tier I assessment
火災危険Combustible. Finely dispersed particles form explosive mixtures in air.
火災の可能性Flammability potential is slight.
有害性の概要A severe eye irritantMay cause skin sensitizationThe substance may have effects on the kidneys, blood and eyes, resulting in kidney impairment, anaemia and lens opacities. [ICSC] Emergency medical treatment: see Phenol. [HSDB] An irritantMay cause injury to eyesMay be absorbed through skin resulting in kidney injury[MSDSonline]
EC 分類Symbol: Xn, NR: 20/22-50S: (2)-24/25-61
UN 分類UN Hazard Class: 9UN Pack Group: III
大気基準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.
Physical DangersDust explosion possible if in powder or granular form, mixed with air.
NFPA Hazard Classification0 - 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.
Toxic Combustion ProductsSpecial hazards arising from the substance or mixture: Carbon oxides.
Hazard Classes and CategoriesAcute Tox. 4 (99.9%)Acute toxicity - category 4Acute toxicity (Oral) - Category 4Serious eye damage/eye irritation - Category 1Acute Tox. 4 *
消火Use water spray, powder, foam, carbon dioxide.
応急処置措置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.Rinse mouth. Give one or two glasses of water to drink. Refer for medical attention .
安全保管Store in an area without drain or sewer access.
Firefighting HazardsCombustible when exposed to heat or flame.
消火手順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.
保管条件Conditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Light sensitive.
清掃方法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.
処分方法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 qualitypotential migration in soil or watereffects on animal and plant lifeand 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.
漏出処分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.
Preventive MeasuresSRP: 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.
Eye PreventionWear safety goggles or eye protection in combination with breathing protection if powder.
Fire PreventionNO open flames. Closed system, dust explosion-proof electrical equipment and lighting. Prevent deposition of dust.
体内負荷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).
生態毒性値LC50Species: Daphnia magna (Water Flea) age 24 hr, juvenile, first instarConditions: freshwater, static, 19.5-20.5 °CConcentration: 3540 ug/L for 48 hr (95% confidence interval: 3170-3950 ug/L)Species: Micropterus salmoides (Largemouth Bass) eggs and larvaeConditions: freshwater, flow through, 20.2-23.2 °C, pH 7.41-8.10, hardness 86.8-116.3 mg/L CaCO3, dissolved oxygen 7.1-8.4 mg/LConcentration: 1000 ug/L for 7 days (95% confidence interval: 290-2270 ug/L)Species: Micropterus salmoides (Largemouth Bass) embryoConditions: freshwater, flow through, 20.2-23.2 °C, pH 7.4-8.1, hardness 86.8-116.3 mg/L CaCO3, dissolved oxygen 7.1-8.4 mg/LConcentration: 6360 ug/L for 72 hr (95% confidence interval: 5850-6910 ug/L)Species: Oncorhynchus mykiss (Rainbow Trout) embryoConditions: freshwater, flow through, 13.3-14.2 °C, pH 7.4-8.1, hardness 86.8-116.3 mg/L CaCO3, dissolved oxygen 8.6-10.2 mg/LConcentration: 80 ug/L for 23 days (95% confidence interval: 60-100 ug/L)For more Ecotoxicity Values (Complete) data for 2-NAPHTHOL (6 total), please visit the HSDB record page.
環境中動態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).
有害作用Skin Sensitizer - An agent that can induce an allergic reaction in the skin.
暴露経路The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
毒性の概要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-toluidinethe semisynthetic penicillin nafcillin, produced via 2-ethoxynaphthaleneand 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/kghowever 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.
生態毒性抜粋/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.
Signs and SymptomsCough. Sore throat.Redness. Pain. Blurred vision.Abdominal pain. Nausea. Vomiting. Diarrhoea.
Ongoing Test StatusEPA has released the first beta version (version 0.5) of the Interactive Chemical Safety for Sustainability (iCSS) Dashboard. The beta version of the iCSS Dashboard provides an interactive tool to explore rapid, automated (or in vitro high-throughput) chemical screening data generated by the Toxicity Forecaster (ToxCast) project and the federal Toxicity Testing in the 21st century (Tox21) collaboration. /The title compound was tested by ToxCast and/or Tox21 assaysSee the data in Chemical Explorer/[USEPAICSS Dashboard ApplicationAvailable from, as of June 27, 2014: http://actor.epa.gov/dashboard/]
Effluent Concentrations2-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 heater2-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).
ICSC Environmental DataThe substance is very toxic to aquatic organisms.
Soil Adsorption/MobilityThe 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).