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ナフタレン 化学構造式
ナフタレン;ナフタレン (1mg/mlメタノール溶液) [水質分析用];ナフタリン;ナフテン;ナフタレン標準品;ナフタレン (50ΜG/ML トルエン溶液);ナフタレン ODOR STANDARD;ナフタレン STANDARD;ナフタレン 溶液;融点スタンダード79~81°C;ナフタレン Standard, 1000 µg/mL in MeOH;ナフタレン, 0.2 mg/mL in MeOH;ナフタレン, 0.5 mg/mL in Acetonitrile;ナフタレン, 2.0 mg/mL in MeOH
Naftalen;whitetar;NAPHTHENE;NAPTHALIN;mighty150;mightyrd1;mothballs;White tar;Albocarbon;NAPHTHALIN
MOL File:

ナフタレン 物理性質

融点 :
80-82 °C (lit.)
沸点 :
218 °C (lit.)
比重(密度) :
4.4 (vs air)
0.03 mm Hg ( 25 °C)
屈折率 :
闪点 :
174 °F
貯蔵温度 :
Store below +30°C.
methanol: soluble50mg/mL, clear, colorless
外見 :
Faint beige to brown to salmon red powder
White to almost white
爆発限界(explosive limit):
水溶解度 :
30 mg/L (25 ºC)
Merck :
Henry's Law Constant:
5.64 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
TLV-TWA 10 ppm (~50 mg/m3) (ACGIH, MSHA, and OSHA); STEL 15 ppm (~75 mg/m3) (ACGIH); IDLH 500 ppm.
CAS データベース:
91-20-3(CAS DataBase Reference)
2B (Vol. 82) 2002
Naphthalene (91-20-3)
  • リスクと安全性に関する声明
  • 危険有害性情報のコード(GHS)
主な危険性  Xn,N,F,T
Rフレーズ  22-40-50/53-67-65-38-11-39/23/24/25-23/24/25-52/53-20
Sフレーズ  36/37-46-60-61-62-45-16-7-33-25-9
RIDADR  UN 1334 4.1/PG 3
WGK Germany  3
RTECS 番号 QJ0525000
自然発火温度 978 °F
国連危険物分類  4.1
容器等級  III
HSコード  29029010
有毒物質データの 91-20-3(Hazardous Substances Data)
毒性 Acute oral LD50 for guinea pigs 1,200 mg/kg, mice 533 mg/kg, rats 1,250 mg/kg (quoted, RTECS, 1985).
化審法 (4)-311 優先評価化学物質
安衛法 特化則 特定化学物質(特定第2類) 変異原性物質
PRTR法 第一種指定化学物質
注意喚起語 Danger
コード 危険有害性情報 危険有害性クラス 区分 注意喚起語 シンボル P コード
H225 引火性の高い液体および蒸気 引火性液体 2 危険 P210,P233, P240, P241, P242, P243,P280, P303+ P361+P353, P370+P378,P403+P235, P501
H228 可燃性固体 可燃性固体 1
P210, P240,P241, P280, P370+P378
H302 飲み込むと有害 急性毒性、経口 4 警告 P264, P270, P301+P312, P330, P501
H304 飲み込んで気道に侵入すると生命に危険のおそ れ 吸引性呼吸器有害性 1 危険
H315 皮膚刺激 皮膚腐食性/刺激性 2 警告 P264, P280, P302+P352, P321,P332+P313, P362
H336 眠気やめまいのおそれ 特定標的臓器毒性、単回暴露; 麻酔作用 3 警告 P261, P271, P304+P340, P312,P403+P233, P405, P501
H351 発がんのおそれの疑い 発がん性 2 警告 P201, P202, P281, P308+P313, P405,P501
H370 臓器の障害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P307+P311, P321,P405, P501
H400 水生生物に強い毒性 水生環境有害性、急性毒性 1 警告 P273, P391, P501
H410 長期的影響により水生生物に非常に強い毒性 水生環境有害性、慢性毒性 1 警告 P273, P391, P501
H412 長期的影響により水生生物に有害 水生環境有害性、慢性毒性 3 P273, P501
P210 熱/火花/裸火/高温のもののような着火源から遠ざ けること。-禁煙。
P261 粉じん/煙/ガス/ミスト/蒸気/スプレーの吸入を避ける こと。
P273 環境への放出を避けること。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P301+P310 飲み込んだ場合:直ちに医師に連絡すること。
P331 無理に吐かせないこと。
P370+P378 火災の場合:消火に...を使用すること。
P403+P235 換気の良い場所で保管すること。涼しいところに 置くこと。

ナフタレン 価格 もっと(52)

メーカー 製品番号 製品説明 CAS番号 包装 価格 更新時間 購入
富士フイルム和光純薬株式会社(wako) W01W0114-0005 ナフタレン 98.0+% (cGC)
Naphthalene 98.0+% (cGC)
91-20-3 500g ¥2500 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01ACSH-152S ナフタレン (50μg/mL トルエン溶液)
Naphthalene (50 ug/mL in Toluene)
91-20-3 1mL ¥5600 2021-03-23 購入
東京化成工業 N0885 ナフタレン >98.0%(GC)
Naphthalene >98.0%(GC)
91-20-3 25g ¥1900 2021-03-23 購入
東京化成工業 N0004 ナフタレン >99.8%(GC)
Naphthalene Zone Refined (number of passes:23) >99.8%(GC)
91-20-3 1sample ¥9600 2021-03-23 購入
関東化学株式会社(KANTO) 18020-2A ナフタレン
91-20-3 5g ¥3200 2021-03-23 購入

ナフタレン MSDS


ナフタレン 化学特性,用途語,生産方法


白色, 結晶又は塊


水に難溶 (3mg/100ml), 各種有機溶剤に可溶。エタノールにやや溶けやすく、水にほとんど溶けない。


C10H8(128.17).石炭タールのナフタレン留分(沸点200~250 ℃)中に多量に存在する炭化水素.また,石油原油および改質油中にも微量存在する."コールタールのナフタレン油から酸性および塩基性物質を抽出して除き,精密蒸留するか,あるいは冷却して結晶を析出させ,遠心分離によって油分を除けば,粗ナフタレンが得られる.合成するには,ベンゼンとアセチレンの混合物を赤熱管中に通じるなどの方法がある.強いコールタール臭をもつ白色の結晶.融点80.3 ℃,沸点218.0 ℃.d204"1.162.n25D"1.5898.λmax 220,275,314 nm(log ε 5.05,3.75,2.50,エタノール).昇華性がある.水に不溶,エタノール,エーテル,ベンゼンなど多くの有機溶媒に可溶.ポリニトロベンゼンやピクリン酸と付加物をつくる.ナフタレンの蒸気を赤熱管中に通すと,2,2′-ビナフチルを生じる.また,酸化すれば1,4-ナフトキノンを経てフタル酸が,水素付加すればテトラリンを経てデカリンが合成できる.ベンゼンと同様,多くの親電子試薬と反応して種々の核置換体を生じるが,ベンゼンよりも反応性が高いため,ジ置換体以上のポリ置換体が生じやすい.また,一般に1位のほうが2位よりも置換されやすい.染料中間体原料,殺虫剤に用いられる.[CAS 91-20-3] 森北出版「化学辞典(第2版)








Naphthalene occurs as transparent prismatic plates also available as white scales, powder balls, or cakes with a characteristic mothball or strong coal tar and aromatic odour. It is sparingly soluble in water but soluble in methanol/ethanol and very soluble in ether. Naphthalene is a commercially important aromatic hydrocarbon. Naphthalene occurs as a white solid or powder. Naphthalene occurs in coal tar in large quantities and is easily isolated from this source in pure condition. It volatilises and sublimes at room temperature above the melting point. The primary use for naphthalene is in the production of phthalic anhydride, also of carbamate insecticides, surface active agents and resins, as a dye intermediate, as a synthetic tanning agent, as a moth repellent, and in miscellaneous organic chemicals. Naphthalene is used in the production of phthalic anhydride; it is also used in mothballs. Naphthalene is also used in the manufacture of phthalic and anthranilic acids to make indigo, indanthrene, and triphenyl methane dyes, for synthetic resins, lubricant, celluloid, lampblack, smokeless powder, and hydronaphthalenes. Naphthalene is also used in dusting powders, lavatory deodorant discs, wood preservatives, fungicide, and as an insecticide. It has been used as an intestinal antiseptic and vermicide and in the treatment of pediculosis and scabies.


Naphthalene is a colorless to brown crystalline solid with a characteristic “moth ball” odor. It evaporates easily and has a strong odor of tar or mothballs. Solubility in water is low (31.7 mg/l at 25 °C), and it is soluble in benzene, alcohol, ether, and acetone (ATSDR, 2005). Shipped as a molten solid.


In 1819, naphthalene was obtained as white crystals during the pyrolysis of coal tar by John Kidd (1775–1851), a British physician and chemist, and Alexander Garden (1757–1829), an American living in Britain. Kidd described the properties of the white crystals he obtained from coal tar and proposed the named naphthaline for the substance; naphthaline was derived from naphtha, a general term for a volatile, fl ammable, hydrocarbon liquid. Michael Faraday (1791–1867) determined the correct empirical formula for naphthalene in 1825, and Richard August Carl Emil Erlenmeyer (1825–1909) proposed the fused benzene ring structure in 1866.


Naphthalene occurs naturally in fossil fuels such as coal and petroleum. It is commonly produced from the distillation and fractionation of coal tar. Naphthalene is used as an intermediate in the production of phthalate plasticizers, other plastics and resins, and other products such as dyes, wood preservatives, explosives, lubricants, pharmaceuticals, deodorizers, and insect repellants. Moth balls and other moth repellants, and some solid block deodorizers used for toilets and diaper pails, are made of crystalline naphthalene (ATSDR, 2005).


In addition to oxidation and reduction reactions, naphthalene readily undergoes substitutionreactions such as nitration, halogenation, sulfonation, and acylation to produce a varietyof other substances, which are used in the manufacture of dyes, insecticides, organic solvents,and synthetic resins. The principal use of naphthalene is for the production of phthalic anhydride,C8H4O3.
Naphthalene is catalytically oxidized to phthalic anhydride: 2C10H8 + 9O2 → 2C4H8O3 +4CO2 + 4H2O using metal oxide catalysts. Phthalic anhydride is used to produce plastics,phthalate plasticizers, insecticides, pharmaceuticals, and resins. Sulfonation of naphthalene withsulfuric acid produces naphthalenesulfonic acids, which are used to produce naphthalene sulfonates.Naphthalene sulfonates are used in various formulations as concrete additives, gypsumboard additives, dye intermediates, tanning agents, and polymeric dispersants. Naphthalene isused to produce carbamate insecticides such as carbaryl, which is a wide-spectrum, generalpurposeinsecticide.


manufacture of phthalic and anthranilic acids which are used in making indigo, indanthrene, and triphenylmethane dyes. manufacture of hydroxyl (naphthols), amino (naphthylamines), sulfonic acid and similar Compounds used in the dye industries. manufacture of synthetic resins, celluloid, lampblack, smokeless powder. manufacture of hydronaphthalenes (Tetralin, Decalin) which are used as solvents, in lubricants, and in motor fuels. Moth repellent and insecticide.


naphthalene: A white volatilesolid, C10H8; r.d. 1.025;m.p. 80.55°C; b.p. 218°C. Naphthaleneis an aromatic hydrocarbon withan odour of mothballs and is obtainedfrom crude oil. It is a raw materialfor making certain syntheticresins.


ChEBI: An aromatic hydrocarbon comprising two fused benzene rings. It occurs in the essential oils of numerous plant species e.g. magnolia.


Naphthalene is produced from coal tar or petroleum. It is made from petroleum by dealkylationof methylnaphthalenes in the presence of hydrogen at high temperature and pressure.Petroleum was a major source of naphthalene until the 1980s, but now most naphthaleneis produced from coal tar. The pyrolysis of bituminous coal produces coke and coke ovengases. Naphthalene is condensed by cooling the coke gas and then separated from the gas.

Synthesis Reference(s)

Journal of the American Chemical Society, 96, p. 3686, 1974 DOI: 10.1021/ja00818a072
The Journal of Organic Chemistry, 54, p. 4474, 1989 DOI: 10.1021/jo00279a046
Tetrahedron Letters, 27, p. 5541, 1986 DOI: 10.1016/S0040-4039(00)85262-4


Heterogeneous ozonolysis of naphthalene adsorbed on XAD-4 resin has been studied using annular denuder technique.


Highly flammable. Insoluble in water.


Vigorous reactions, sometimes amounting to explosions, can result from the contact between aromatic hydrocarbons, such as Naphthalene, and strong oxidizing agents. They can react exothermically with bases and with diazo compounds. Substitution at the benzene nucleus occurs by halogenation (acid catalyst), nitration, sulfonation, and the Friedel-Crafts reaction. Naphthalene, camphor, glycerol, or turpentine will react violently with chromic anhydride [Haz. Chem. Data 1967. p 68]. Friedel-Crafts acylation of Naphthalene using benzoyl chloride, catalyzed by AlCl3, must be conducted above the melting point of the mixture, or the reaction may be violent [Clar, E. et al., Tetrahedron, 1974, 30, 3296].


Toxic by inhalation. Upper respiratory tract irritant, cataracts and hemolytic anemia. Possible carcinogen.


Inhalation of naphthalene vapor may causeirritation of the eyes, skin, and respiratorytract, and injury to the cornea. Other symptoms are headache, nausea, confusion, andexcitability. The routes of exposure of thiscompound into the body are inhalation, ingestion, and absorption through the skin; andthe organs that may be affected are the eyes,liver, kidney, blood, skin, and central nervoussystem.
The most severe toxic effects from naphthalene, however, may come from oral intakeof large doses of this compound. In animals, as well as in humans, ingestion of largeamounts may cause acute hemolytic anemiaand hemoglobinuria attributed to its metabolites, 1- and 2-naphthol and naphthoquinones.Infants are more sensitive than adults becauseof their lower capacity for methemoglobinreduction. Other symptoms from ingestion ofnaphthalene are gastrointestinal pain and kidney damage. The LD50 values reported inthe literature show variation among differentspecies. In mice, an oral LD50 value may beon the order of 600 mg/kg. Symptoms of respiratory depression and ataxia were noted.
Chronic exposure to naphthalene vapormay affect the eyes, causing opacities of thelens and optical neuritis. The acute effectsfrom inhalation of its vapors at high concentrations are nausea and vomiting.
Inhalation studies have shown positivetumorigenic response in mice. Studies conducted under National Toxicology Program(NTP) show clear evidence of carcinogenicityin rats resulting from inhalation of naphthalene vapors (NTP 2000). Increased incidencesof respiratory epithelial adenoma and olfactory epithelial neuroblastoma in the nose wereobserved in both the sexes of rats. On thebasis of these findings IARC has reevaluatednaphthalene and reclassified it under Group2B carcinogen, as possibly carcinogenic tohumans (IARC 2002)..


Flammable/combustible material. May be ignited by friction, heat, sparks or flames. Some may burn rapidly with flare burning effect. Powders, dusts, shavings, borings, turnings or cuttings may explode or burn with explosive violence. Substance may be transported in a molten form at a temperature that may be above its flash point. May re-ignite after fire is extinguished.


Human poison by ingestion. Experimental poison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by subcutaneous route. An experimental teratogen. Experimental reproductive effects. An eye and skin irritant. Can cause nausea, headache, daphoresis, hematuria, fever, anemia, liver damage, vomiting, convulsions, and coma. Poisoning may occur by ingestion of large doses, inhalation, or skin absorption. Questionable carcinogen with experimental tumorigenic data. Flammable when exposed to heat or flame; reacts with oxidizing materials. Explosive reaction with dinitrogen pentaoxide. Reacts violently with CrOs, aluminum chloride + benzoyl chloride. Fires in the benzene scrubbers of coke oven gas plants have been attributed to oxidation of naphthalene. Explosive in the form of vapor or dust when exposed to heat or flame. To fight fire, use water, CO2, dry chemical. When heated to decomposition it emits acrid smoke and irritating fumes.


Naphthalene is used as a chemical intermediate or feedstock for synthesis of phthalic, anthranilic, hydroxyl (naphthols), amino (naphthylamines), and sulfonic compounds; which are used in the manufacture of various dyes and in the preparation of phthalic anhydride, 1-naphthyl-N-methyl carbonate; and β-naphthol. Naphthalene is also used in the manufacture of hydronaphthalenes, synthetic resins; lampblack, smokeless powder; and celluloid. Naphthalene has been used as a moth repellent.
Approximately 100 million people worldwide have G6PD deficiency which would make them more susceptible to hemolytic anemia on exposure to naphthalene. At present, more than 80 variants of this enzyme deficiency have been identified. The incidence of this deficiency is 0.1% in American and European Caucasians, but can range as high as 20% in American blacks and greater than 50% in certain Jewish groups. Newborn infants have a similar sensitivity to the hemolytic effects of naphthalene, even without G6PD deficiency.


Naphthalene is reasonably anticipated to be a human carcinogenbased on sufficient evidence from studies in experimental animals.


Schauer et al. (1999) reported naphthalene in diesel fuel at a concentration of 600 μg/g and in a diesel-powered medium-duty truck exhaust at an emission rate of 617 μg/km. Detected in distilled water-soluble fractions of 87 octane gasoline (0.24 mg/L), 94 octane gasoline (0.21 mg/L), Gasohol (0.29 mg/L), No. 2 fuel oil (0.60 mg/L), jet fuel A (0.34 mg/L), diesel fuel (0.25 mg/L), military jet fuel JP-4 (0.18 mg/L) (Potter, 1996), and used motor oil (116 to 117 μg/L) (Chen et al., 1994). Lee et al. (1992) investigated the partitioning of aromatic hydrocarbons into water. They reported concentration ranges from 350 to 1,500 mg/L and 80 to 300 μg/L in diesel fuel and the corresponding aqueous phase (distilled water), respectively. Diesel fuel obtained from a service station in Schlieren, Switzerland contained 708 mg/L naphthalene (Schluep et al., 2001). California Phase II reformulated gasoline contained naphthalene at a concentration of 1.04 g/kg. Gas-phase tailpipe emission rates from gasoline-powered automobiles with and without catalytic converters were approximately 1.00 and 50.0 mg/km, respectively (Schauer et al., 2002).
Thomas and Delfino (1991) equilibrated contaminant-free groundwater collected from Gainesville, FL with individual fractions of three individual petroleum products at 24–25 °C for 24 h. The aqueous phase was analyzed for organic compounds via U.S. EPA approved test method 625. Average naphthalene concentrations reported in water-soluble fractions unleaded gasoline, kerosene, and diesel fuel were 989, 644, and 167 ug/L.
Based on laboratory analysis of 7 coal tar samples, naphthalene concentrations ranged from 940 to 71,000 ppm (EPRI, 1990). Detected in 1-yr aged coal tar film and bulk coal tar at concentraions of 26,000 and 29,000 mg/kg, respectively (Nelson et al., 1996). A high-temperature coal tar contained naphthalene at an average concentration of 8.80 wt % (McNeil, 1983). Nine commercially available creosote samples contained naphhalene at concentrations ranging from 3,800 to 52,000 mg/kg (Kohler et al., 2000). Lee et al. (1992a) equilibrated eight coal tars with distilled water at 25 °C. The maximum concentration of naphthalene observed in the aqueous phase was 14 mg/L.
Naphthalene was detected in soot generated from underventilated combustion of natural gas doped with toluene (3 mole %) (Tolocka and Miller, 1995).
Typical concentration in a heavy pyrolysis oil is 17.8 wt % (Chevron Phillips, May 2003). Detected in asphalt fumes at an average concentration of 1.15 ng/m3 (Wang et al., 2001).
An impurity identified in commercially available acenaphthene (Marciniak, 2002).
Schauer et al. (2001) measured organic compound emission rates for volatile organic compounds, gas-phase semi-volatile organic compounds, and particle-phase organic compounds from the residential (fireplace) combustion of pine, oak, and eucalyptus. The gas-phase emission rate of naphthalene was 227 mg/kg of pine burned. Emission rates of naphthalene were not measured during the combustion of oak and eucalyptus.


Biological. In activated sludge, 9.0% of the applied amount mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Under certain conditions, Pseudomonas sp. oxidized naphthalene to cis- 1,2-dihydro-1,2-dihydroxynaphthalene (Dagley, 1972). This metabolite may be oxidized by Pseudomonas putida to carbon dioxide and water (Jerina et al., 1971). Under aerobic conditions, Cunninghamella elegans degraded naphthalene to 1-naphthol, 2-naphthol, trans-1,2-dihydroxy 1,2-dihydronaphthalene, 4-hydroxy-1-tetralone, and 1,4-naphthoquinone. Under aerobic conditions, Agnenellum, Oscillatoria, and Anabaena degraded naphthalene to 1-naphthol, cis-1,2- dihydroxy-1,2-dihydronaphthalene, and 4-hydroxy-1-tetralone (Kobayashi and Rittman, 1982; Riser-Roberts, 1992). Candida lipolytica, Candida elegans, and species of Cunninghamella, Syncephalastrum and Mucor oxidized naphthalene to 1-naphthol, 2-naphthol, trans-1,2- dihydroxy-1,2-dihydronaphthalene, 4-hydroxy-1-tetralone, 1,2-naphthoquinone, and 1,4-naphthouinone (Cerniglia et al., 1978, 1980; Dodge and Gibson, 1980).
Soil. The half-lives of naphthalene in pristine and oil-contaminated sediments are >88 d and 4.9 h, respectively (Herbes and Schwall, 1978). Reported half-lives for naphthalene in a Kidman sandy loam and McLaurin sandy loam are 2.1 and 2.2 d, respectively (Park et al., 1990).
Surface Water. The volatilization half-life of naphthalene from surface water (1 m deep, water velocity 0.5 m/sec, wind velocity 22.5 m/sec) using experimentally determined Henry’s law constants is estimated to be 16 h (Southworth, 1979). The reported half-lives of naphthalene in an oil-contaminated estuarine stream, clean estuarine stream, coastal waters, and in the Gulf stream are 7, 24, 63, and 1,700 d, respectively (Lee, 1977). Mackay and Wolkoff (1973) estimated an evaporation half-life of 2.9 h from a surface water body that is 25 °C and 1 m deep. In a laboratory experiment, the average volatilization half-life of naphthalene in a stirred water vessel (outer dimensions 22 x 10 x 21 cm) at 23 °C and an air flow rate of 0.20 m/sec is 380 min. The half-life was independent of wind velocity or humidity but very dependent upon temperature (Kl?pffer et al., 1982).
Groundwater. The estimated half-life of naphthalene in groundwater in the Netherlands was 6 months (Zoeteman et al., 1981). Nielsen et al. (1996) studied the degradation of naphthalene in a shallow, glaciofluvial, unconfined sandy aquifer in Jutland, Denmark. As part of the in situ microcosm study, a cylinder that was open at the bottom and screened at the top was installed through a cased borehole approximately 5 m below grade. Five liters of water was aerated with atmospheric air to ensure aerobic conditions were maintained. Groundwater was analyzed weekly for approximately 3 months to determine naphthalene concentrations with time. The experimentally determined first-order biodegradation rate constant and corresponding half-life following a 6-d lag phase were 0.8/d and 20.8 h, respectively.
Photolytic. Irradiation of naphthalene and nitrogen dioxide using a high pressure mercury lamp (λ >290 nm) yielded the following principal products: 1- and 2-hydroxynaphthalene, 1-hydroxy-2- nitronaphthalene, 1-nitronaphthalene, 2,3-dinitronaphthalene, phthalic anhydride, 1,3-, 1,5- and 1,8-dinitronaphthalene (Barlas and Parlar, 1987). In a similar experiment, naphthalene crystals was heated to 50 °C and exposed to pure air containing NO and OH radicals. Photodecomposition followed first-order kinetics indicating the concentration of OH radicals remained constant throughout the reaction. Degradation products identified by GC/MS were 1-naphthol, 2-naphthol, 1-nitronaphthalene, 2-nitronaphthalene, 1,4-naphthoquinone, 1,4-naphthoquinone-2,3-epoxide, 3- nitrophthalic anhydride, phthalic anhydride, 4-methyl-2H-1-benzopyran-2-one, 1(3H)-isobenzofuranone, 1,2-benzenecarboxaldehyde, cis-2-formyl-cinnamaldehyde, trans-2-formylcinnamaldehyde, and phthalide. The following compounds were tentatively identified: 2,7-naphthalenediol, 2-nitro-1-naphthol, 4-nitro-1-naphthol, and 2,4-dinitro-1-naphthol. Photoproducts identified by HPLC included: benzoic acid, cinnamic acid, 2,4-dinitro-1-naphthol, 2-formylcinnamic acid, cis-2-formylcinnamaldehyde, trans-2-formylcinnamaldehyde, 1-nitronaphthalene, 2-nitronaphthalene, 1-naphthol, 2-naphthol, 1,4-naphthoquinone, 1,4-naphthoquinone-2,3-epoxide, 3-nitrophthalic anhydride, oxalic acid, phthalic acid, phthalaldehyde, and phthalide (Lane et al., 1997).


UN1334 Naphthalene, crude or Naphthalene, refined, Hazard Class: 4.1; Labels: 4.1-Flammable solid. UN2304 (molten) Hazard Class: 4.1; Labels: 4.1-Flammable solid.


Crystallise naphthalene once or more times from the following solvents: EtOH, MeOH, CCl4, *C6H6, glacial acetic acid, acetone or diethyl ether, followed by drying at 60o in an Abderhalden drying apparatus. It has also been purified by vacuum sublimation and by fractional crystallisation from its melt. Other purification procedures include refluxing in EtOH over Raney Ni and chromatography of a CCl4 solution on alumina with *benzene as eluting solvent. Baly and Tuck [J Chem Soc 1902 1908] purified naphthalene for spectroscopy by heating with conc H2SO4 and MnO2, followed by steam distillation (repeating the process), and formation of the picrate which, after recrystallisation (m 150o) is decomposed with base and the naphthalene is steam distilled. It is then crystallised from dilute EtOH. It can be dried over P2O5 under vacuum (take care not to make it sublime). Also purify it by sublimation and subsequent crystallisation from cyclohexane. Alternatively, it has been washed at 85o with 10% NaOH to remove phenols, with 50% NaOH to remove nitriles, with 10% H2SO4 to remove organic bases, and with 0.8g AlCl3 to remove thianaphthalenes and various alkyl derivatives. Then it is treated with 20% H2SO4, 15% Na2CO3 and finally distilled. [Gorman et al. J Am Chem Soc 107 4404 1985.] Zone refining purified naphthalene from anthracene, 2,4-dinitrophenylhydrazine, methyl violet, benzoic acid, methyl red, chrysene, pentacene and indoline. [Beilstein 5 IV 1640.]

Toxicity evaluation

Systemic absorption of naphthalene vapor may result in cataracts. The biochemical basis for naphthalene cataract has been investigated. Naphthalene is metabolized in the liver to 1,2-dihydro-1,2-dihydroxynaphthalene. Lenticular catechol reductase biotransforms 1,2-dihydro-1,2-dihydroxynaphthalene to 1,2-dihydroxynaphthalene, which, in turn, is auto-oxidized in air at neutral pH to 1,2-naphthoquinone and hydrogen peroxide. Ascorbic acid reverses the latter reaction and forms dehydroascorbic acid, which diffuses out of the lens very slowly. Dehydroascorbic acid has been shown to accumulate in the lens of rabbits that were fed naphthalene and lens incubated in vitro with 1,2-dihydro- 1,2-dihydroxynaphthalene. The sequence of reactions involves the reduction of ascorbic acid by 1,2-naphthoquinone in the aqueous humor to dehydroascorbic acid, which rapidly penetrates the lens and is reduced by glutathione. Oxidized glutathione and 1,2-naphthoquinone may compete for enzyme glutathione reductase, which normally maintains high reticular levels of reduced glutathione. A reduction in the concentration of these coupled with the removal of oxygen from the aqueous humor due to the autooxidation of 1,2-dihydroxynaphthalene may make the lens sensitive to naphthalene toxicity.


Dust may form explosive mixture with air. Incompatible with oxidizers (chlorates, nitrates, peroxides, permanganates, perchlorates, chlorine, bromine, fluorine, etc.); contact may cause fires or explosions. Keep away from alkaline materials, strong bases, strong acids, oxoacids, epoxides. Violent reactions with chromium(III) oxide, dinitrogen pentoxide; chromic anhydride.


Dissolve or mix the material with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber. All federal, state, and local environmental regulations must be observed. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.

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  • 91-20-3
  • 'LGC' (2402)
  • 'LGC' (2603)
  • Albocarbon
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  • Dezodorator
  • Mighty 150
  • Mighty rd1
  • mighty150
  • mightyrd1
  • Moth balls
  • Moth flakes
  • mothballs
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  • Naftalen
  • naftalen(polish)
  • naphtalene
  • naphthalene,crude
  • Naphthaleneball
  • Naphthaline
  • Napthalene, molten
  • NCI-C52904
  • Rcra waste number U165
  • ナフタレン
  • ナフタレン (1mg/mlメタノール溶液) [水質分析用]
  • ナフタリン
  • ナフテン
  • ナフタレン標準品
  • ナフタレン (50ΜG/ML トルエン溶液)
  • ナフタレン STANDARD
  • ナフタレン 溶液
  • 融点スタンダード79~81°C
  • ナフタレン Standard, 1000 µg/mL in MeOH
  • ナフタレン, 0.2 mg/mL in MeOH
  • ナフタレン, 0.5 mg/mL in Acetonitrile
  • ナフタレン, 2.0 mg/mL in MeOH
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