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1,4-ナフトキノン
1,4-ナフトキノン · α-ナフトキノン · 1,4-ナフタレンジオン · ナフタレン-1,4-ジオン · 1,4-ジヒドロナフタレン-1,4-ジオン · ナフトキノン · 1,4-ナフトキノン標準品 · １，４ナフタレンジオン
識別子と物理属性
| CAS No. | 130-15-4 |
|---|---|
| 分子式 | C10H6O2 |
| 平均分子量 | 158.15 g/mol |
| 単同位体質量 | 158.03677943 g/mol |
| SMILES | O=C1C=CC(=O)c2ccccc21 |
| InChIKey | FRASJONUBLZVQX-UHFFFAOYSA-N |
| PubChem CID | 8530 |
| ChEMBL | CHEMBL55934 |
| ChEBI | CHEBI:27418 |
| EC No. | 204-977-6 |
| DTXSID | DTXSID5040704 |
| 現地名 | 1,4-ナフトキノン |
化学・物理的性質
| XLogP | 1.7 |
|---|---|
| 極性表面積 | 34.1 |
| 水素結合供与体数 | 0 |
| 水素結合受容体数 | 2 |
| 回転可能結合数 | 0 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 227 |
| LogP（分配係数） | log Kow = 1.711.8 |
| 臭い | Odor like that of benzoquinone |
| 密度 | 1.422 (NTP, 1992) - Denser than waterwill sink1.4 g/cm³1.422 no temp1,42 g/cm3 |
| Color/Form | Yellow triclinic needles from alcohol or petroleum etherYELLOW POWDERYellow crystals |
| 溶解度 | less than 1 mg/mL at 70 °F (NTP, 1992)Sol in alkali hydroxide solnsparingly sol in cold waterslightly sol in petroleum etherfreely sol in carbon disulfide, acetic acid, hot alcohol, ether, benzene, and chloroformVery soluble in alkali hydroxide solutions.Volatile with steam.In water, 0.35 g/100 ml at 25 °CSolubility in water, g/100ml at 25 °C: 0.350.09g/リットル不溶性 |
| 沸点 | Sublimes below 212 °F (NTP, 1992)243.22°C (rough estimate) |
| Decomposition | When heated to decomposition it emits acrid smoke and irritating fumes. |
| 融点 | 277 °F (NTP, 1992)128.5 °C126 °C119-122 °C(lit.) |
| 蒸気密度 | 5.46 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density (air = 1): 5.5 |
| 蒸気圧 | 0.00018 [mmHg]2.6 Pa at 50 °C (= 0.0195 mm Hg at 50 °C)Vapor pressure, Pa at 50 °C: 2.60.0195 [mm Hg] @50 °C<1 hPa (50 °C) |
| Heat of Combustion | 1100.8 kcal (solid) |
| Physical Description | 1,4-naphthoquinone appears as yellow needles or brownish green powder with an odor of benzoquinone. (NTP, 1992)Dry PowderYellow solid with a pungent odor[ICSC] "Begins to sublimes below 100 deg C." [Merck Index]YELLOW CRYSTALS OR FLAKES WITH PUNGENT ODOUR. |
| 屈折率 | 1.5300 (estimate) |
| 引火点 | 141 °C |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 粉 |
| 色 | カーキ |
| pH | 6.1 (10g/l, H2O, 20℃) |
| Merck | 14,6395 |
| BRN | 878524 |
| ヘンリー定数 | 5.0×103 mol/(m3Pa) at 25℃, HSDB (2015) |
| 安定性 | 安定。強力な還元剤、強力な酸化剤とは相容れない。 |
| InChI | 1S/C10H6O2/c11-9-5-6-10(12)8-4-2-1-3-7(8)9/h1-6H |
| InChIKey | FRASJONUBLZVQX-UHFFFAOYSA-N |
| SMILES | O=C1C=CC(=O)c2ccccc12 |
| LogP（分配係数） | 1.71-1.77 at 25℃ |
| CAS データベース | 130-15-4(CAS DataBase Reference) |
| NISTの化学物質情報 | 1,4-Naphthalenedione(130-15-4) |
| EPAの化学物質情報 | 1,4-Naphthoquinone (130-15-4) |
化学的特性
1,4-Naphthoquinone is a yellow to greenish yellow crystalline solid that has pungent odor like benzoquinone. It is slightly soluble in water, soluble in ether, chloroform, benzene, glacial acetic acid. In alkaline solutions it produces a reddish-brown color.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.8% (5 of 620) of reports.DangerH301 (99.2%): Toxic if swallowed [Danger Acute toxicity, oral]H314 (32.3%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]H315 (66.9%): Causes skin irritation [Warning Skin corrosion/irritation]H317 (88.4%): May cause an allergic skin reaction [Warning Sensitization, Skin]H318 (30.3%): Causes serious eye damage [Danger Serious eye damage/eye irritation]H319 (66.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H330 (95%): Fatal if inhaled [Danger Acute toxicity, inhalation]H334 (17.1%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory]H335 (81.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]H400 (95%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]H410 (37.3%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]P233, P260, P261, P264, P264+P265, P270, P271, P272, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P320, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P363, P391, P403, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 620 reports by companies from 34 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Reported as not meeting GHS hazard criteria per 5 of 620 reports by companies.There are 33 notifications provided by 615 of 620 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| 規制情報 | Chemical: 1,4-NaphthalenedioneRegulation (EC) No 1107/2009 (amended)1,4-Naphthalenedione is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,4-Naphthalenedione 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: 11-11-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/22758Status: Cease Manufacture Update: 24-11-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/212651,4-Naphthoquinone: Does not have an individual approval but may be used under an appropriate group standardThe 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.) |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | Flash point data for this compound are not availablehowever, it is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 健康有害性 | ACUTE/CHRONIC HAZARDS: When heated to decomposition this chemical emits toxic fumes and smoke. (NTP, 1992) |
| 有害性の概要 | A skin, eye, and respiratory tract irritant[ICSC] Very toxic after ingestion, inhalation, or skin contactEffects on experimental animals include somnolence, weight loss, liver injury, methemoglobinemia, tumors, and reproductive changes[MSDSonline] |
| 反応性グループ | Ketones |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: III |
| RCRA 要件 | U166As stipulated in 40 CFR 261.33, when 1,4-naphthoquinone, 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). |
| Reactivity Profile | 1,4-NAPHTHOQUINONE may react with many acids and bases liberating heat and flammable gases (e.g., H2). The heat may be sufficient to start a fire in the unreacted portion of the ketone. May react with reducing agents such as hydrides, alkali metals, and nitrides to produce flammable gas (H2) and heat. Incompatible with isocyanates, aldehydes, cyanides, peroxides, and anhydrides. May react violently with aldehydes, HNO3, HNO3 + H2O2, and HClO4. |
| Chemical Dangers | Decomposes on burning. This produces toxic fumes. |
| Air and Water Reactions | Insoluble in water. |
| EPA Hazardous Waste Number | U1661,4-Naphthoquinone |
| 消火 | Fires involving this material can be controlled with a dry chemical, carbon dioxide, foam, or Halon extinguisher. (NTP, 1992)Use water spray, powder, foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer 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. Give one or two glasses of water to drink. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give a slurry of activated charcoal in water to drink. Refer for medical attention . |
| 応急処置 | 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.SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment.INHALATION: IMMEDIATELY leave the contaminated areatake deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be usedif not available, use a level of protection greater than or equal to that advised under Protective Clothing.INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992) |
| 安全保管 | Well closed. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.STORAGE PRECAUTIONS: You should protect this chemical from exposure to light. Keep the container tightly closed under an inert atmosphere, and store under refrigerated temperatures. (NTP, 1992) |
| 処分方法 | [40 CFR 240-280, 300-306, 702-799 (7/1/2005)] Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U166, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.Good candidate for rotary kiln incineration, with a temperature range of 820 to 1,600 °C and a residence time of seconds. Also a good candidate for fluidized bed incineration, with a temp range of 450 to 980 °C and a residence time of seconds. |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered containers. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:IMMEDIATE PRECAUTIONARY MEASURE: Isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids.SPILL: Increase the immediate precautionary measure distance, in the downwind direction, as necessary.FIRE: If tank, rail tank car or highway tank is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directionsalso, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2024) |
| Eye Prevention | Wear face shield or eye protection in combination with breathing protection. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | A harmful concentration of airborne particles can be reached quickly when dispersed. |
| Skin Prevention | Protective gloves. |
| 相互作用 | The addition of sublytic concentrations of both naphthoquinones and heme leads to a synergistic lysis of the organisms /Trypanosoma brucei/ in vitro. /Naphthoquinones/The mechanisms of toxicity of 1-naphthol and two of its metabolites 1,2-, and 1,4-naphthoquinone, to freshly isolated rat hepatocytes was studied. 1-Naphthol and both naphthoquinones exhibited a dose-dependent toxicity to hepatocytes. (14)C-1-Naphthol was metabolized by hepatocytes predominantly to its glucuronate and sulfate conjugates, but small amounts of covalently bound products were also formed. Blebbing on the surface of the hepatocytes was observed following exposure to 1-naphthol and the naphthoquinones, together with a dose-dependent decr in intracellular GSH, which preceded the onset of cytotoxicity. The toxicity of 1-naphthol and the naphthoquinones was potentiated by dicoumarol, an inhibitor of DT-diaphorase (NADPH:quinone oxidoreductase). This enhanced toxicity was accompanied by a greater amount of surface blebbing, an increased depletion of intracellular GSH, particularly in the case of 1-naphthol and 1,4-naphthoquinone, and a decreased metabolism of 1-naphthol to its conjugates with variable effects on the amount of covalently bound products formed. Apparently, the toxicity of 1-naphthol may be mediated by the formation of 1,2-naphthoquinone and/or 1,4-naphthoquinone, which may then be metabolized by 1-electron reduction to naphthoquinone radicals. These, in turn, may covalently bind to important cellular macromolecules or enter a redox cycle with molecular oxygen thereby generating active oxygen species. Both of these processes appear to play a role in producing the cytotoxic effects of 1-naphthol.1,4-Naphthoquinone completely inhibited the gametotoxic effect of human chorionic gonadotropin in toads.A study determined whether taurine would protect isolated rat hepatocytes against the cytotoxic effects of three different toxic compounds, carbon-tetrachloride (CCl4), hydrazine, and 1,4-naphthoquinone. Hepatocytes were isolated from male Sprague-Dawley-rats and exposed to vapor from 7.5, 10, and 15 uL of CCl4. Only those exposed to the highest level demonstrated a marked loss of viability (70%) and lactate-dehydrogenase (LDH) leakage (35%). The addition of taurine showed a dose related protection against cytotoxicity measured as leakage of LDH after 45 minutes. Cells exposed to 1,4-naphthoquinone demonstrated a dose related decrease in hepatocyte viability, a corresponding increase in LDH leakage, and a decrease in ATP after 180 minutes of incubation. Taurine caused an attenuation of the cytotoxicity with the dose response relationship being shifted to the right with a statistically significant difference in viability, LDH leakage, and ATP depletion compared to 1,4-naphthoquinone alone at an exposure level of 100 umol. Hepatocytes incubated with various concentrations of hydrazine demonstrated a dose dependent loss of cell viability and an increase in leakage of LDH. Taurine (15 mM) significantly reduced this trypan-blue uptake and LDH leakage after exposure to 20 mM and 24 mM hydrazine. Taurine had no effect on depletion of ATP at any hydrazine concentration. The authors conclude that taurine is able to protect hepatocytes against cytotoxicity caused by different compounds.Possible antimutagenic activity of 26 vitamins and related compounds - ascorbic acid, beta-carotene, cyanocobalamin, folic acid, nicotinic acid, nicotinamide, pantothenic acid, pyridoxale, pyridoxamine, pyridoxine, retinal, retinol, retinoic acid, retinyl acetate, retinyl palmitate, riboflavin, riboflavin 5'-phosphate, flavin adenine dinucleotide (FAD), alpha-tocopherol, alpha-tocopherol acetate, vitamins K(1), K(3), K(4), 1,4-naphthoquinone, and coenzyme Q(10) - was tested against six heterocyclic amine (HCA) mutagens, i.e., 2-amino-3-methyl-imidazo[4, 5-f]quinoline (IQ), 2-amino-3,4-dimethyl-imidazo[4,5-f]quinoline (MeIQ), 2-amino-3,8-dimethyl-imidazo[4,5-f]quinoxaline (MeIQx), 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), 2-amino-6-methyl-dipyrido[1,2-a:3',2'-d]imidazole (Glu-P-1) and 3-amino-1-methyl-5H-pyrido[4,3-b]indole (Trp-P-2) in the Salmonella/reversion assay using tester strains Salmonella typhimurium TA 98 and TA 100. Retinol, retinal, riboflavin, riboflavin 5'-phosphate, FAD, vitamins K(1), K(3), K(4), 1,4-naphthoquinone, and coenzyme Q(10) caused a concentration-dependent decrease in the mutagenicity of all six mutagens in both tester strains. Quantification of antimutagenic potencies by calculating ID(50)1000vitamin K(1): 401-740vitamin K(3) (menadione): 85-590vitamin K(4): 45-3131,4-naphthoquinone: 170-290coenzyme Q(10): 490-860. In general, there were no major differences between HCAs tested except in part with Trp-P-2 nor between the two tester strains. In enzyme kinetic experiments with Salmonella, retinol, vitamins K(3), and K(4) behaved as competitive inhibitors of IQ induced mutagenesis. However, at the highest concentration of menadione (200 nmol/plate) and of riboflavin 5'-phosphate (2000 nmol/plate), non-competitive inhibition was observed. At other concentrations of riboflavin 5'-phosphate and at all concentrations of FAD, meaningful interpretation of enzyme kinetics were not possible. Reduction of the activity of 7-eth |
| 生態毒性値 | LD50 Peromyscus maniculatus (Deer mouse) oral 470 mg/kgLC50 Abra aequalis (Common atlantic abra) 60 mg/L/14 daysstatic /formulated product/LC50 Anabaena variabilis (Blue-green algae) >100 mg/L/14 daysLC50 Chlorella pyrenoidosa (Green algae) >100 mg/L/14 daysFor more Ecotoxicity Values (Complete) data for 1,4-NAPHTHOQUINONE (9 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 16(SRC), determined from a structure estimation method(2), indicates that 1,4-naphthoquninone is expected to have very high mobility in soil(SRC). Volatilization of 1,4-naphthoquinone from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.97X10-9 atm-cu m/mole(SRC), using a fragment constant estimation method(3). 1,4-Naphthoquinone is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.69X10-4 mm Hg(SRC), determined from a fragment constant method(4). 1,4-Naphthoquinone absorbs at wavelengths between 290 and 520 nm(5) and therefore is expected to be susceptible to direct photolysis by sunlight(SRC). 1,4-Naphthoquinone (at 500 mg/kg soil) required 9 days for complete biodegradation in chernozem soil(6). 1,4-Naphthoquinone (at 1000 mg/kg soil) was 80% degraded within 22 days in a chernozem soil(7) and had a half-life of 1.2 days in soil in another study(8).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 16(SRC), determined from a structure estimation method(2), indicates that 1,4-naphthoquinone is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.97X10-9 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 0.6(SRC), from its log Kow of 1.71(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). 1,4-Naphthoquinone is oxidized in a standard biodegradability test utilizing a sewage inoculum, having a 5 day BOD of 38% of the theoretical value(8).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-naphthoquinone, which has an estimated vapor pressure of 1.69X10-4 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. However, monitoring data have detected 1,4-naphthoquinone adsorbed to atmospheric particulate matter collected from urban air samples(3,4), waste incinerator fly ash(5), tailpipes of diesel and gasoline engines(6) and emissions from wood combustion(7,8). Vapor-phase 1,4-naphthoquinone 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 about 5 days(SRC), calculated from its rate constant of 3.1X10-12 cu cm/molecule-sec at 25 °C(9). Vapor-phase 1,4-naphthoquinone is also degraded in the atmosphere by reaction with ozonethe half-life for this reaction in air is estimated to be about 6.5 hours(SRC), calculated from its rate constant of 1.75E-18 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(10). 1,4-Naphthoquinone absorbs at wavelengths between 290 and 520 nm(11) and therefore is expected to be susceptible to direct photolysis by sunlight(SRC). Particulate-phase 1,4-naphthoquinone may be removed from the air by wet or dry deposition(SRC). |
| 有害作用 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Methemoglobinemia - The presence of increased methemoglobin in the bloodthe compound is classified as secondary toxic effect |
| 暴露経路 | The substance can be absorbed into the body by inhalation and by ingestion. |
| 生態毒性抜粋 | /AQUATIC SPECIES/ /It is toxic to/ ... blue algae ... /at concentrations of/ 0.3-0.6 mg/L. |
| Signs and Symptoms | Cough. Sore throat. Burning sensation.Redness. Burning sensation. Pain.Redness. Pain. Blurred vision.Abdominal pain. Nausea. Vomiting. |
| Effluent Concentrations | 1,4-Naphthoquinone was present in the flue gas following circulating fluid bed combustion of coal (Ruhr coal = 67,000 ng/normalized cu mPoland coal = 6800 ng/normalized cu mSouth Africa coal = 310 ng/normalized cu mSpitsbergen coal = not detected)(1). 1,4-Naphthoquinone was qualitatively detected in incinerator fly ash from a municipal waste incinerator in Japan(2). 1,4-Naphthoquinone concn of 0.007-0.051 mg/g (organic carbon emitted) was detected in the fine particle emissions from fireplace combustion of six species of woods grown in the northern US (red maple, northern red oak, paper birch, eastern white pine, eastern hemlock, balsam fir)(3). 1,4-Naphthoquinone concn of 0.006-0.018 mg/g (organic carbon emitted) was detected in the fine particle emissions from fireplace combustion of six species of woods grown in the southern US (yellow poplar, white ash, sweet-gum, mockernut hickory, loblolly pine slash pine)(4).1,4-Naphthoquinone was detected in particulate emissions collected from the tailpipes of diesel vehicles at concn of 4-8 ug/g (extract mass) and concn of 10 ug/g from gasoline engines in Japan(1). |
| ICSC Environmental Data | The substance is very toxic to aquatic organisms. |
| Soil Adsorption/Mobility | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,4-naphthoquinone can be estimated to be 16(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,4-naphthoquinone is expected to have very high mobility in soil. |
| Atmospheric Concentrations | URBAN/SUBURBAN: 1,4-Naphthoquinone was qualitatively detected in size-segregated atmospheric particles taken from air samples collected from a monitoring station roof in Kenmore Station, Boston, MA in the summer of 1994(1). 1,4-Naphthoquinone was qualitatively detected in particulates collected from urban air in Leeds, UK(2).SOURCE DOMINATED: Air samples from a freeway tunnel in Japan contained a 1,4-naphthoquinone concn of 4 ug/g (extract mass)(1). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Quinones were ... suspected and shown to be responsible for brown discoloration of the cornea and exposed bulbar conjunctiva which gradually developed in workers ... long exposed to vapors associated with manufacturing and commercial application of synthetic aniline dyes ... /Quinones//SIGNS AND SYMPTOMS/ Chronic neurotoxic effects include vision disturbances. /From table/BIOMONITORING/ Toxicological manifestations of 1,4-naphthoquinone include decreased number of erythrocytes in the blood, decresed sulfhydryl compounds and hemoglobin levels in the blood, hepatotoxicity, and depressed phagocytic activity of leukocytes. It also caused the appearance of methemoglobin and Heinz bodies in the blood. |
| CERCLA 報告数量 | 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 5,000 lb or 2,270 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV. D.3.b). |
| F | 8 |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | QL7175000 |
| 輸送番号（UN） | UN 2811 6.1/PG 1 |
| 毒性 | LD50 orally in Rabbit: 190 mg/kg LD50 dermal Rat 202 mg/kg |
| 税関コード | 29146910 |
| 危険文句（R） | 25-26-36/37/38-43-50-34-11 |
| 化審法 | (4)-372 |
| 安衛法 | 変異原性物質 |
| 危険表示 | T+,N,T,C,F |
| hazard_note | Very Toxic |
| 安全措置（S） | 26-36/37-45-61-38-36/37/39-28A-24-16 |
| 危険等級 | 6.1Acute Tox. 1 InhalationAcute Tox. 3 OralAquatic Acute 1Aquatic Chronic 1Eye Dam. 1Skin Corr. 1CSkin Sens. 1STOT SE 3 |
| 包装等級 | I |
| 貯蔵分類 | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| 有害物質データ | 130-15-4(Hazardous Substances Data) |
用途
解説
naphthalenedione．C10H6O2(158.16)．ナフタレン核をもつキノンであるが，1,2-，1,4-および2,6-ナフトキノンの3種類の異性体がある． 1,2-および1,4-ナフトキノンは，それぞれ1-アミノ-2-ナフトールあるいは4-アミノ-1-ナフトールを二クロム酸カリウムの希硫酸溶液で酸化すると得られる．ナフトキノンは，ナフタレン環骨格をもつキノン。いずれもキノン特有の色をもっている結晶である。1,4-ナフトキノンの誘導体は動物色素として天然に分布している。単にナフトキノンというと1,4-ナフトキノンをさす。ナフトキノン系染料やビタミンKも1,4-ナフトキノンの骨格をもっている。1,2-ナフトキノンは赤色の結晶で有毒である。ディーゼルエンジンの排気ガスに含まれている。2,6-ナフトキノンは不安定で、溶液中ではすぐに分解する（図）。1,2-ナフトキノンは赤色の結晶．分解点115～120 ℃．λmax 250，340，405 nm(log ε 4.35，3.40，3.40)．エタノール，ベンゼン，エーテルに可溶，水に不溶．濃硫酸呈色は緑色．1,4-ナフトキノンは五酸化バナジウム系触媒によるナフタレンの空気酸化によっても得られる．黄色の昇華性結晶．融点125 ℃．特異臭があり，水蒸気蒸留される．アルカリ水溶液に溶けて赤褐色を呈する．ビタミンKはその誘導体である．2,6-ナフトキノンはamphi-ナフトキノンともいわれ，2,6-ジヒドロキシナフタレンを酸化鉛(Ⅳ)で酸化すると得られる．橙色の結晶．分解点130～135 ℃．森北出版「化学辞典（第2版）
用途
ゴム及びポリエステル樹脂の重合調整剤として、染料ならびに医薬品の合成に用いられる。アントラキノンの製造中間体
用途
有機合成原料
使用
1,4-Naphthoquinone is used as a strong dienophile in Diels-Alder reaction. It is also used as a precursor to anthroquinone and 5-nitro-1,4-naphthalenedione, which finds application in the preparation of aminoanthroquinone and is also used as a dye precursor. It is a basic component of Vitamin K.
一般的な説明
Yellow needles or brownish green powder with an odor of benzoquinone.
使用用途
ナフトキノンは、さまざまな工業的用途を持つ化学物質を合成する原料として使用されています。ディールス・アルダー反応の名で知られるナフトキノンと1,3-ジエンの反応では、アントラキノンを合成可能です。アントラキノンは、さまざまな色素の原料やパルプを製造する際の触媒として用いられます。 また、ナフトキノンのジアゾ誘導体であるジアゾナフトキノンは、半導体の製造過程における水銀露光などに用いられています。ナフトキノンの誘導体には細胞毒性を持つものが多く、抗ウイルス剤や解熱剤などに使用されるものもあります。 1,4-ナフトキノンおよびその誘導体は、抗菌、抗真菌、抗ウイルス、抗炎症、抗がんなどの薬理作用が報告されており、これらの効果を利用した医薬品が開発されています。また、そのほか、高い着色力を持つため、染料や顔料として用いられます。特に、赤色や黄色の染料には、ナフトキノン誘導体が有用です。
製法・合成法
製造方法
ナフトキノンの製造方法 1,4-ナフトキノンは、通常、ナフタレンから誘導されます。ナフタレンにクロム酸ナトリウムなどの酸化剤を作用させることで、1,4-ナフトキノンが生成されます。 また、他の方法として、アントラキノン誘導体の環縮合や、1,4-ナフトールの酸化などが挙げられます。
合成方法
ナフタレンを空気酸化することにより製造される。
純化方法
Crystallise the quinone from diethyl ether (charcoal). It distils in steam. It also crystallises from *benzene or aqueous EtOH and sublimes in a vacuum. [Beilstein 7 IV 2422.]