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ニトロベンゼン 化学構造式
ニトロベンゼン;1-ニトロベンゼン;4-ニトロベンゼン;2-ニトロベンゼン;3-ニトロベンゼン;ニトロベンゾール;ニトロベンゼン標準品;ニトロベンゼン REAGENTPLUS,99%;ニトロベンゼン 溶液;ニトロベンゼン, 100 µg/mL in MeOH;ニトロベンゼン, 100 µg/mL in MeOH:AcCN (50:50);ニトロベンゼン, 1000 µg/mL in MeOH;ニトロベンゼン, 1000 µg/mL in MeOH:AcCN (50:50);ニトロベンゼン, 99%
NCI-C60082;Nitrobenzen;NITROBENZOL;MYRBANE OIL;MIRBANE OIL;Nitrobenzeen;nitro-benzen;Mitrobenzole;NITROBENZENE;oilofmyrbane
MOL File:

ニトロベンゼン 物理性質

融点 :
5-6 °C (lit.)
沸点 :
210-211 °C (lit.)
比重(密度) :
1.196 g/mL at 25 °C (lit.)
4.2 (vs air)
0.15 mm Hg ( 20 °C)
屈折率 :
n20/D 1.551(lit.)
闪点 :
190 °F
貯蔵温度 :
Store below +30°C.
3.98(at 0℃)
外見 :
Clear yellow
8.1 (1g/l, H2O, 20℃)
Relative polarity:
爆発限界(explosive limit):
水溶解度 :
slightly soluble
Merck :
Henry's Law Constant:
9.86 at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
TLV-TWA 1 ppm (~5 mg/m3) (ACGIH, MSHA, and OSHA); IDLH 200 ppm (NIOSH).
Stable. Incompatible with strong oxidizing agents, strong reducing agents, strong bases. Flammable. Note wide explosion limits.
CAS データベース:
98-95-3(CAS DataBase Reference)
Benzene, nitro-(98-95-3)
2B (Vol. 65) 1996
Nitrobenzene (98-95-3)
  • 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  T,N,F,Xn
Rフレーズ  23/24/25-40-48/23/24-51/53-62-39/23/24/25-11-36/37/38-60-52/53-48/23/24/25-36-20/21/22
Sフレーズ  28-36/37-45-61-28A-16-7-27-53-26
RIDADR  UN 1662 6.1/PG 2
WGK Germany  2
RTECS 番号 DA6475000
自然発火温度 899 °F
国連危険物分類  6.1
容器等級  II
HSコード  29042010
有毒物質データの 98-95-3(Hazardous Substances Data)
毒性 LD50 orally in rats: 600 mg/kg (PB91-108398)
消防法 危険物第4類第三石油類(非水溶性)
化審法 (3)-436 優先評価化学物質
安衛法 57,57-2
PRTR法 第一種指定化学物質
毒劇物取締法 劇物
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
H227 引火性液体 引火性液体 4 警告 P210, P280, P370+P378, P403+P235,P501
H300 飲み込むと生命に危険 急性毒性、経口 1, 2 危険 P264, P270, P301+P310, P321, P330,P405, P501
H310 皮膚に接触すると生命に危険 急性毒性、経皮 1, 2 危険 P262, P264, P270, P280, P302+P350,P310, P322, P361, P363, P405, P501
H330 吸入すると生命に危険 急性毒性、吸入 1, 2 危険 P260, P271, P284, P304+P340, P310,P320, 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
H361 生殖能または胎児への悪影響のおそれの疑い 生殖毒性 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
H372 長期にわたる、または反復暴露により臓器の障 害 特定標的臓器有害性、単回暴露 1 危険 P260, P264, P270, P314, P501
H401 水生生物に毒性 水生環境有害性、急性毒性 2 P273, P501
H411 長期的影響により水生生物に毒性 水生環境有害性、慢性毒性 2
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
P201 使用前に取扱説明書を入手すること。
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。
P280 保護手袋/保護衣/保護眼鏡/保護面を着用するこ と。
P304 吸入した場合:
P308+P313 暴露または暴露の懸念がある場合:医師の診断/手当てを 受けること。
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。

ニトロベンゼン 価格 もっと(35)

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) W01ACSAPP-9-143 ニトロベンゼン
Nitrobenzene, 100 ug/mL in MeOH
98-95-3 1mL ¥4400 2021-03-23 購入
富士フイルム和光純薬株式会社(wako) W01ACSAPP-9-143-10X ニトロベンゼン
Nitrobenzene, 1000 ug/mL in MeOH
98-95-3 1mL ¥7400 2021-03-23 購入
東京化成工業 N0758 ニトロベンゼン >99.5%(GC)
Nitrobenzene >99.5%(GC)
98-95-3 500g ¥2600 2021-03-23 購入
関東化学株式会社(KANTO) 28196-01 ニトロベンゼン >99.0%(GC)
Nitrobenzene >99.0%(GC)
98-95-3 500mL ¥2100 2021-03-23 購入
関東化学株式会社(KANTO) 28196-00 ニトロベンゼン >99.5%(GC)
Nitrobenzene >99.5%(GC)
98-95-3 500mL ¥2200 2021-03-23 購入

ニトロベンゼン 化学特性,用途語,生産方法


無色~うすい黄色, 澄明の液体


水に微溶 (0.2g/100ml水), アルコール, ベンゼンに易溶。エタノール及びジエチルエーテルには極めて溶けやすく、水にはほとんど溶けない。


アニリン原料,M-ジニトロベンゼン原料,M-クロロニトロベンゼン原料,M-ニトロベンゼンスルホン酸原料,染料?香料中間体 (NITE CHRIP)






Nitrobenzene is a greenish-yellow crystal or yellow oily liquid, and is slightly soluble in water. The primary hazard of nitrobenzene is toxicity; however, it is also combustible. The boiling point is about 410°F, the flash point is 190°F, and the ignition temperature is 900°F. The specific gravity is 1.2, which is heavier than water, and the material will sink to the bottom. The vapor density is 4.3, which is heavier than air. Nitrobenzene is toxic by ingestion, inhalation, and skin absorption, with a TLV of 1 ppm in air. The four-digit UN identification number is 1652. The NFPA 704 designation is health 3, flammability 2, and reactivity 1. Nitrobenzene is a nitro hydrocarbon derivative, but it is not very explosive. The primary uses are as a solvent, an ingredient of metal polishes and shoe polishes, and in the manufacture of aniline.


Aromatic nitro compounds mixed with nitrobenzene are explosives of high sensitivity and detonation velocities and are spark detonatable).


yellow liquid


Nitrobenzene is a pale yellow to dark brown oily liquid whose odor resembles bitter almonds (or black paste shoe polish).


Clear, light yellow to brown, oily liquid with an almond-like or shoe polish odor. May darken on exposure to air. An experimentally determined odor threshold concentration of 4.7 ppbv was reported by Leonardos et al. (1969). A detection odor threshold concentration of 9.6 mg/m3 (1.9 ppmv) was determined by Katz and Talbert (1930).


The primary use of nitrobenzene is in the captive production of aniline, with about 97.5% of nitrobenzene production consumed in this process. The major use of aniline is in the manufacture of polyurethanes. Nitrobenzene is also used as a solvent in petroleum refining, in the manufacture of cellulose ethers and acetate, and in Friedel-Crafts reactions to hold the catalyst in solution. It is also used in the synthesis of other organic compounds including acetaminophen, which is an over-the-counter analgesic commonly known as Tylenol?.
Nitrobenzene is used as a flavoring agent, a perfume for soaps and as a solvent for shoe dyes.


Most nitrobenzene (97%) is used in the manufacture of aniline (IARC 1996, HSDB 2009). Miscellaneous uses include the manufacture of benzidine, quinoline, azobenzene, pyroxylin compounds, isocyanates, pesticides, rubber chemicals, pharmaceuticals, and dyes such as nigrosines and magenta. Nitrobenzene is found in soaps and shoe and metal polishes and is used as a solvent for cellulose ester, in modifying esterification of cellulose acetate, and in refining lubricating oils (HSDB 2009). Nitrobenzene also is used as a solvent in petroleum refining and the synthesis of other organic compounds, such as acetaminophen (ATSDR 1990).


Nitrobenzene is an organic compound used a standard for detection and analyses as well as its removal from the environment. The compound’s cytotoxic effects have been studied in a hepatocarcinoma cell line.


For the manufacture of aniline; in soaps, shoe polishes; for refining lubricating oils; manufacture of pyroxylin Compounds.


ChEBI: A nitroarene consisting of benzene carrying a single nitro substituent. An industrial chemical used widely in the production of aniline.


Nitrobenzene is produced commercially by the exothermic nitration of benzene with fuming nitric acid in the presence of a sulfuric acid catalyst at 50 to 65℃. The crude nitrobenzene is passed through washer-separators to remove residual acid and is then distilled to remove benzene and water.


Nitrobenzene is produced by the direct nitration of benzene with a mixture of sulfuric and nitric acids. U.S. capacity for nitrobenzene production is approximately 1.5 billion pounds . The most important use for nitrobenzene is in the production of aniline. Nearly 98% of the nitrobenzene produced in the U.S. is converted to aniline.


A yellow organic oil obtained by refluxing benzene with a mixture of concentrated nitric and sulfuric acids. The reaction is a typical electrophilic substitution on the benzene ring by the nitryl cation (NO2+).


nitrobenzene: A yellow oily liquid,C6H5NO2; r.d. 1.2; m.p. 6°C; b.p.211°C. It is made by the nitration ofbenzene using a mixture of nitricand sulphuric acids.

Synthesis Reference(s)

Journal of the American Chemical Society, 95, p. 5198, 1973 DOI: 10.1021/ja00797a017
Tetrahedron Letters, 27, p. 2335, 1986 DOI: 10.1016/S0040-4039(00)84522-0


Very slightly soluble in water.


Aluminum chloride added to Nitrobenzene containing about 5% phenol caused a violent explosion [Chem. Eng. News 31:4915. 1953]. Heating a mixture of Nitrobenzene, flake sodium hydroxide and a little water led to an explosion, discussed in [Bretherick's 5th ed. 1995]. Mixed with oxidants, i.e. dinitrogen tetraoxide, fluorodinitromethane, nitric acid, peroxodisulfuric acid, sodium chlorate, tetranitromethane, uranium perchlorate, etc., forms highly sensitive explosive, [Bretherick 5th ed, 1995]. Heated mixtures of Nitrobenzene and tin(IV) chloride produce exothermic decomposition with gas production [Bretherick, 5th Ed., 1995].


Toxic by ingestion, inhalation, and skin absorption. Methemoglobinemia. Possible carcinogen.


The routes of entry of nitrobenzene intothe body are the inhalation of its vaporsor absorption of the liquid or the vaporthrough the skin and, to a much lesserextent, ingestion. The target organs are theblood, liver, kidneys, and cardiovascular system. Piotrowski (1967) estimated that in anexposure period of 6 hours to a concentration of 5 mg/m3, 18 mg of nitrobenzene wasabsorbed through the lungs and 7 mg throughthe skin in humans. Furthermore, about 80%of inhaled vapor is retained in the respiratorytract. The dermal absorption rate at this concentration level is reported as 1 mg/h, whilethe subcutaneous absorption of the liquidis between 0.2 and 0.3 mg/cm3/h (ACGIH1986).
The symptoms of acute toxicity are headache, dizziness, nausea, vomiting, and dyspnea. Subacute and chronic exposure cancause anemia. Nitrobenzene effects the conversion of hemoglobin to methemoglobin. Itis metabolized to aminophenols and nitrophenols to about 30%, which are excreted.


Moderate explosion hazard when exposed to heat or flame. Reacts violently with nitric acid, aluminum trichloride plus phenol, aniline plus glycerine, silver perchlorate and nitrogen tetroxide. Avoid aluminum trichloride; aniline; gycerol; sulfuric acid; oxidants; phosphorus pentachloride; potassium; potassium hydroxide. Avoid sunlight, physical damage to container, freezing, and intense heat.


Nitrobenzene is mainly utilized for aniline production. The aniline is used primarily for the manufacture of 4,4'-methylenebis (phenyl isocyanate) and polymers thereof (50%). The second largest use of aniline is in the manufacture of chemicals for rubber production (30%). Dyes and dye intermediates, hydroquinone and drugs account for about 8% of the aniline produced, while 10% of the aniline is converted to agricultural products such as pesticides and defoliants (Northcott 1978). It also is used as a solvent for cellulose ethers and an ingredient in polishes for metals and shoes (HSDB 1988).


Confirmed carcinogen. Human poison by an unspecified route. Poison experimentally by subcutaneous and intravenous routes. Moderately toxic by ingestion, skin contact, and intraperitoneal routes. Human systemic effects by ingestion: general anesthetic, respiratory stimulation, and vascular changes. An experimental teratogen. Experimental reproductive effects. Mutation data reported. An eye and skin irritant. Can cause cyanosis due to formation of methemoglobin. It is absorbed rapidly through the skin. The vapors are hazardous. to heat and flame. Moderate explosion hazard when exposed to heat or flame. Explosive reaction with solid or concentrated alkali + heat (e.g., sodium hydroxide or potassium hydroxide), aluminum chloride + phenol (at 12O°C), aniline + glycerol + sulfuric acid, nitric + sulfuric acid + heat. Forms explosive mixtures with aluminum chloride, oxidants (e.g., fluorodinitromethane, uranium perchlorate, tetranitromethane, sodium chlorate, nitric acid, nitric acid + water, peroxodsulfuric acid, dinitrogen tetraoxide), phosphorus pentachloride, potassium, sulfuric acid. Reacts violently with aniline + glycerin, N20, AgCLO4. To fight fne, use water, foam, CO2, dry chemical. Incompatible with potassium hydroxide. When heated to decomposition it emits toxic fumes of NOx. See also NITRO COMPOUNDS OF AROMATIC HYDROCARBONS.


Nitrobenzene is used in the manufacture of explosives and aniline dyes and as solvent and intermediate. It is also used in floor polishes; leather dressings and polished; and paint solvents, and to mask other unpleasant odors. Substitution reactions with nitrobenzene are used to form m-derivatives. Pregnant women may be especially at risk with respect to nitrobenzene as with many other chemical compounds, due to transplacental passage of the agent. Individuals with glucose-6-phosphate dehydrogenase deficiency may also be special risk groups. Additionally, because alcohol ingestion or chronic alcoholism can lower the lethal or toxic dose of nitrobenzene, individuals consuming alcoholic beverages may be at risk.


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


Biological. In activated sludge, 0.4% of the applied nitrobenzene mineralized to carbon dioxide after 5 d (Freitag et al., 1985). Under anaerobic conditions using a sewage inoculum, nitrobenzene degraded to aniline (Hallas and Alexander, 1983). When nitrobenzene (5 and 10 mg/L) was statically incubated in the dark at 25 °C with yeast extract and settled domestic wastewater inoculum, complete biodegradation with rapid acclimation was observed after 7 to 14 d (Tabak et al., 1981). In activated sludge inoculum, 98.0% COD removal was achieved in 5 d. The average rate of biodegradation was 14.0 mg COD/g?h (Pitter, 1976).
Razo-Flores et al. (1999) studied the fate of nitrobenzene (50 mg/L) in an upward-flow anaerobic sludge bed reactor containing a mixture of volatile fatty acids and/or glucose as electron donors. The nitrobenzene loading rate and hydraulic retention time for this experiment were 43 mg/L?d and 28 h, respectively. Nitrobenzene was effectively reduced (>99.9%) to aniline (92% molar yield) in stoichiometric amounts for the 100-d experiment.
Photolytic. Irradiation of nitrobenzene in the vapor phase produced nitrosobenzene and 4- nitrophenol (HSDB, 1989). Titanium dioxide suspended in an aqueous solution and irradiated with UV light (λ = 365 nm) converted nitrobenzene to carbon dioxide at a significant rate (Matthews, 1986). A carbon dioxide yield of 6.7% was achieved when nitrobenzene adsorbed on silica gel was irradiated with light (λ >290 nm) for 17 h (Freitag et al., 1985).
Chemical/Physical. In an aqueous solution, nitrobenzene (100 μM) reacted with Fenton’s reagent (35 μM). After 15 min, 2-, 3-, and 4-nitrophenol were identified as products. After 6 h, about 50% of the nitrobenzene was destroyed. The pH of the solution decreased due to the formation of nitric acid (Lipczynska-Kochany, 1991). Augusti et al. (1998) conducted kinetic studies for the reaction of nitrobenzene (0.2 mM) and other monocyclic aromatics with Fenton’s reagent (8 mM hydrogen peroxide; [Fe+2] = 0.1 mM) at 25 °C. They reported a reaction rate constant of 0.0260/min.


Nitrobenzene vapor is readily absorbed through the skin and lungs. At an airborne nitrobenzene concentration of 10 mg/m3 humans may absorb 18 to 25 mg in 6 h through the lungs and from 8 to 19 mg through the skin in the same length of time .
Urine is the major route of excretion of nitrobenzene metabolites in rabbits , rats and mice . The most abundant metabolite in earlier studies in rabbits and rats was p-aminophenol. This compound, or its glucuronide or sulfate conjugates, accounted for 19% to 31% of the dose. In a later study in rats in which the acid hydrolysis step employed by earlier workers to cleave conjugates was replaced by enzyme hydrolysis, no p-aminophenol was found in the urine of male Fischer-344 or CD rats .
About 9% of a nitrobenzene dose was excreted by B6C3F1 mice as the sulfate conjugate. The major metabolites found in Fischer-344 rat urine were p-hydroxyacetanilide sulfate (19% of the dose), p-nitrophenol sulfate (20% of the dose) and m-nitrophenol sulfate (10% of the dose) .
In addition, an unidentified metabolite accounted for about 10% of the dose .
Male CD rats excreted the same metabolites after an oral dose of nitrobenzene, but in slightly different proportions. They excreted about half as much of the dose as the glucuronide or sulfate conjugates of P-hydroxyacetanilide (9% of the dose) and P-nitrophenol (13% of the dose), approximately the same amount of m-nitrophenol (8% of the dose), and about twice as much as the unidentified metabolite. Interestingly, whereas Fischer-344 rats excreted the phenolic metabolites of nitrobenzene exclusively as sulfates, CD rats excreted the same metabolites in the free form (15-17% of the total metabolite) and as glucuronides (4-20% of the total metabolite).
Approximately 4% of the dose also was excreted as p-hydroxyacetanilide by B6C3F1 mice and as p- and m-nitrophenol (7% and 6% of the dose, respectively) sulfates, glucuronides and free metabolites .
Clearly, ring hydroxylation and reduction are important metabolic steps in the biotransformation of nitrobenzene in rabbits, rats, mice and humans . Since no significant isotope effect was found in the metabolism of deuterated nitrobenzene to these products in rats in vivo , the o- and p-nitrophenols may be formed through an arene oxide intermediate. A significant isotope effect was noted in the formation of m-nitrophenol from deuterated nitrobenzene in the same rats, leading to the conclusion that m-nitrophenol is formed by a direct oxygen insertion mechanism or by some other mechanism which does not involve an arene oxide intermediate. The reduction of nitrobenzene in vivo is largely, if not exclusively, due to the action of anaerobic intestinal microflora. Treatment with antibiotics totally eliminated the ability of cecal contents of Fischer-344 rats to reduce nitrobenzene in vitro, and rats treated with antibiotics eliminated p-hydroxyacetanilide as 0.9% of an oral dose of nitro-benzene. Normal rats excreted 16.2% of an oral dose of nitrobenzene as that metabolite .
The reduction of most nitro compounds by hepatic microsomes is not detectable under aerobic conditions, but is readily observable under anaerobic conditions. Mason and Holtzman proposed that the first intermediate in the microsomal reduction of nitroaromatic compounds is the nitro anion radical, the product of a one electron transfer to nitrobenzene or other nitroaromatic compound. Oxygen would rapidly oxidize the radical to yield the parent nitro compound and Superoxide anion. Both the nitro anion radical and Superoxide anion are potentially toxic compounds.
Both P-nitrophenol and P-aminophenol have been detected in human urine after exposure to nitrobenzene. p-Aminophenol has been found only after large accidental exposures and acid hydrolysis of urine. Since acid conditions convert p-acetamidophenol to P-aminophenol, the identity of the metabolite actually excreted is in doubt. P-Nitrophenol has been found in the urine of volunteers exposed to low inhalation doses of nitrobenzene, and Kuzelova and Popler have suggested that urinary P-nitrophenol be used to monitor exposure to nitrobenzene.


UN1662 Nitrobenzene, Hazard Class: 6.1; Labels: 6.1-Poisonous materials.


Common impurities include nitrotoluene, dinitrothiophene, dinitrobenzene and aniline. Most impurities can be removed by steam distillation in the presence of dilute H2SO4, followed by drying with CaCl2, and shaking with, then distilling at low pressure from BaO, P2O5, AlCl3 or activated alumina. It can also be purified by fractional crystallisation from absolute EtOH (by refrigeration). Another purification process includes extraction with aqueous 2M NaOH, then water, dilute HCl, and water, followed by drying (CaCl2, MgSO4 or CaSO4) and fractional distillation under reduced pressure. The pure material is stored in a brown bottle, in contact with silica gel or CaH2. It is very hygroscopic. [Beilstein 5 H 233, 5 I 124, 5 II 171, 5 III 591, 5 IV 708.]

Toxicity evaluation

The intermediates and products of nitrobenzene reduction can cause methemoglobinemia (a condition in which the blood’s ability to carry oxygen is reduced) by accelerating the oxidation of hemoglobin to methemoglobin. Three primary metabolic mechanisms have been identified: reduction of nitrobenzene to aniline by intestinal microflora, its reduction to aniline occurring in hepatic microsomes and erythrocytes, and nitrobenzene oxidative metabolism to the nitrophenols by hepatic microsomes. Many of the toxicological effects are likely triggered by metabolites of nitrobenzene. For example, methemoglobinemia is caused by the interaction of hemoglobin with the products of nitrobenzene reduction (i.e., nitrosobenzene, phenylhydroxylamine, and aniline). The anaerobic metabolism occurring in the gastrointestinal track is much faster than reduction by the hepatic microsomal fraction; therefore, the action of bacteria normally present in the small intestine is an important element in the formation of methemoglobin.


Concentrated nitric acid, nitrogen tetroxide; caustics; phosphorus pentachloride; chemically-active metals, such as tin or zinc. Violent reaction with strong oxidizers and reducing agents. Attacks many plastics. Forms thermally unstable compounds with many organic and inorganic compounds.


Incineration (982℃, 2.0 seconds minimum) with scrubbing for nitrogen oxides abatement . 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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