化工社化工社 化学情報印刷レポート · 研究参考用
3,4-ジクロロニトロベンゼン
3,4-ジクロロニトロベンゼン · 1-ニトロ-3,4-ジクロロベンゼン · 1,2-ジクロロ-4-ニトロベンゼン · 3,4-ジクロロ-1-ニトロベンゼン · 3，4ジクロロニトロベンゼン · 1・2-ジクロロ-4-ニトロベンゼン · 3,4‐ジクロロニトロベンゼン · 1,2-DICHLORO-4-NITROBENZENE
識別子と物理属性
| CAS No. | 99-54-7 |
|---|---|
| 分子式 | C6H3Cl2NO2 |
| 平均分子量 | 192 g/mol |
| 単同位体質量 | 190.9540837 g/mol |
| SMILES | O=[N+]([O-])c1ccc(Cl)c(Cl)c1 |
| InChIKey | NTBYINQTYWZXLH-UHFFFAOYSA-N |
| PubChem CID | 7443 |
| ChEMBL | CHEMBL167468 |
| EC No. | 202-764-2 |
| DTXSID | DTXSID8024999 |
| 現地名 | 3,4-ジクロロニトロベンゼン |
化学・物理的性質
| XLogP | 3.1 |
|---|---|
| 極性表面積 | 45.8 |
| 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 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 159 |
| 物質分類 | Nitrogen Compounds -> Nitros, Aromatic |
| SpringerMaterials Properties | Boiling point |
| LogP（分配係数） | log Kow = 3.12 |
| 密度 | 1.4558 at 167 °F (NTP, 1992) - Denser than waterwill sink1.4558 at 75 °C/4 °CDensity (at 15 °C): 1.56 g/cm³1.48 g/cm3 (55℃) |
| Color/Form | Needles from alcoholSOLID |
| 溶解度 | less than 0.1 mg/mL at 74.3 °F (NTP, 1992)Soluble in ether, alcoholslightly soluble in carbon tetrachlorideIn water, 121 mg/L at 20 °CSolubility in water: none0.151g/リットル151mg/L（20℃） |
| 引火点 | 255 °F (NTP, 1992)124 °C |
| 沸点 | 491 to 493 °F at 760 mmHg (NTP, 1992)255-256 °C255 °C255-256 °C(lit.) |
| 融点 | 109 °F (NTP, 1992)43 °CHas both a stable and labile form. The stable alpha-form has a melting point of 42-43 °C and beta-form is a liquid which changes to the alpha-form at 15 °C39-41 °C39-41 °C(lit.) |
| 蒸気密度 | 6.63 (NTP, 1992) - Heavier than airwill sink (Relative to Air)Relative vapor density (air = 1): 6.6 |
| 蒸気圧 | 0.01 [mmHg]1.03X10-2 mm Hg at 25 °CVapor pressure, Pa at 25 °C: 20.01 hPa (20 °C) |
| ヘンリー定数 | Henry's Law constant = 8.07X10-6 amt-cu m/mol at 25 °C |
| 屈折率 | 1.5929 (estimate) |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 結晶質量 |
| 色 | 黄色から茶色 |
| 凝固点 | 30~31℃ |
| BRN | 1818163 |
| ヘンリー定数 | 1.2×100 mol/(m3Pa) at 25℃, Altschuh et al. (1999) |
| 安定性 | 安定。強酸化剤、強塩基とは相容れない。 |
| InChI | 1S/C6H3Cl2NO2/c7-5-2-1-4(9(10)11)3-6(5)8/h1-3H |
| InChIKey | NTBYINQTYWZXLH-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1ccc(Cl)c(Cl)c1 |
| CAS データベース | 99-54-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzene, 1,2-dichloro-4-nitro-(99-54-7) |
| EPAの化学物質情報 | 3,4-Dichloronitrobenzene (99-54-7) |
化学的特性
colourless to yellow crystals or beige powder
安全性と法規制
| GHS 分類 | WarningH302 (97.9%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P391, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 47 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.DangerH302: Harmful if swallowed [Warning Acute toxicity, oral] |
|---|---|
| 規制情報 | Chemical: Benzene, 1,2-dichloro-4-nitro-TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.Status: Active Update: 20-12-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/121461,2-Dichloro-4-nitrobenzene: 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 - Benzene, 1,2-dichloro-4-nitro-: Human health tier II assessment |
| 輸送ラベル（DOT） | Poison |
| 火災危険 | This chemical is combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| 火災の可能性 | Fire risk by spontaneous reaction. |
| 健康有害性 | SYMPTOMS: Symptoms of exposure to this compound include eye, skin, and mucous membrane irritationheadachedrowsinessand unsteadiness. Chronic symptoms include liver damage. |
| 有害性の概要 | A skin and eye irritantMay cause effects on the blood[ICSC] May cause liver damage[CAMEO] Causes methemoglobinemia in high-dose animals experimentsMethemoglobinemia also reported in exposed workersDermal LD50 (rats) >2000 mg/kgOral LDLo (rabbits) = 950 mg/kg[HSDB] An eye irritantCan be absorbed through skinMay cause skin sensitizationMay induce methemoglobinemiaEffects in high-dose animal studies include cyanosis[MSDSonline] No evidence of skin sensitization[INCHEM: SIDS] Danger of cutaneous absorptionCould be carcinogenic for man but not conclusive because of insufficient data[MAK] |
| 反応性グループ | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| UN 分類 | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | Organisation for Economic Cooperation and DevelopmentScreening Information Data Set for 1,2-Dichloro-4-nitrobenzene, CAS # 99-54-7 (2003). A compliation of the chemical properties, toxicity and pharmacokinetics of 1,2-dichloro-4-nitrobenzene used for the initial assesment of the test compound. Includes an IUCLID dataset updated in 2004 as an appendix.European Chemicals BureauIUCLID Dataset, 1,2-Dichloro-4-Nitrobenzene (CAS # 99-54-7) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of July 5, 2007. A report on the ecotoxicity, toxicity, and pharmacokinetics of 1,2-dichlor-4-nitrobenzene. |
| TSCA 要件 | Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 3,4-Dichloronitrobenzene is included on this list.Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. |
| Reactivity Profile | Can react vigorously with oxidizing materials. (NTP, 1992) |
| 消火 | Fires involving this compound can be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use powder, water spray, foam, carbon dioxide. |
| 応急処置措置 | Fresh air, rest.Rinse and then wash skin with water and soap.Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth. |
| 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. |
| 安全保管 | Separated from strong oxidants, strong bases and food and feedstuffs. Provision to contain effluent from fire extinguishing. |
| 非火災時の漏出対応 | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with ethanol 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. |
| 処分方法 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant lifeand conformance with environmental and public health regulations.The following wastewater treatment technologies have been investigated for nitrobenzene: Activated carbon and stripping. /Nitrobenzene/ |
| 漏出処分 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment. |
| Isolation and Evacuation | Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. Prevent deposition of dust. Closed system, dust explosion-proof electrical equipment and lighting. |
| Inhalation Risk | No indication can be given about the rate at which a harmful concentration of this substance in the air is reached on evaporation at 20 °C. |
| Skin Prevention | Protective gloves. |
| 相互作用 | Kinetic studies of glutathione transferase activites in which nafenopin was mixed with normal rat liver cytosols in the assay system revealed competitive type inhibition toward 3,4-dichloronitrobenzene. |
| 生態毒性値 | LC50 Leuciscus idus /(Ide)/ 3.1 mg/L for 48 hr /Conditions of bioassay not specified in source examined/LC50 Leuciscus idus /(Ide)/ 5.6 mg/L for 96 hr /Conditions of bioassay not specified in source examined/LC50 Leusiscus Idus melanotus /golden orfe/ 5.2 mg/L for 96 hr /Static bioassay/LC50 Oryzias latipes /Japanese medaka/ 7 mg/L for 48 hr/ Static bioassay |
| 環境中動態 | TERRESTRIAL FATE: Based on a classification scheme(1), measured Koc values of 390 to 393(2,3), indicate that 3,4-dichloronitrobenzene is expected to have moderate mobility in soil(SRC). Volatilization of 3,4-dichloronitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 8.07X10-6 atm-cu m/mole(4). 3,4-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.03X10-2 mm Hg(5). Lack of biodegradation of 3,4-dichloronitrobenzene incubated in an aquifer slurry over an unspecified time frame(6) suggests that biodegradation is not an important environmental fate process in soil(SRC). However, under anaerobic conditions using a river sediment, a half-life of 2.4 days has been reported(7).AQUATIC FATE: Based on a classification scheme(1), measured Koc values of 390 to 393 in silt loams(2,3), indicate that 3,4-dichloronitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon a Henry's Law constant of 8.07X10-6 atm-cu m/mole(5). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 6 days and 51 days, respectively(SRC). According to a classification scheme(6), a BCF values ranging from 104 to 130(7,8) suggest the potential for bioconcentration in aquatic organisms is high(SRC). Lack of biodegradation of 3,4-dichloronitrobenzene incubated in an aquifer slurry over an unspecified time frame(9) suggests that biodegradation is not an important environmental fate process in water(SRC). However, under anaerobic conditions using a river sediment, a half-life of 2.4 days has been reported(10).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3,4-dichloronitrobenzene, which has a /an estimated vapor pressure of 1.03X10-2 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 3,4-dichloronitrobenzene 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 321 days(SRC), calculated from its rate constant of 5.0X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 3,4-Dichloronitrobenzene contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(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. |
| 暴露経路 | The substance can be absorbed into the body by ingestion. |
| 毒性の概要 | Human Health: 1,2-Dichloro-4-nitrobenzene is absorbed from the gastro-intestinal tract and although there are some species differences in experimental animals from the available data it can be concluded that 1,2-dichloro-4-nitrobenzene is excreted mainly via urine in the form of the mercapturic acid derivative N-acetyl-S-(2-chloro-4-nitrophenyl)-Lcysteine. ... Based on the results of the acute dermal toxicity study with rats the LD50 is > 2000 mg/kg bw. From studies with rabbits no LD50 could be derived, the lowest Lethal Dose Level (LDLo) was 950 mg/kg bw. The acute oral toxicity in rats ranges from 625 to 950 mg/kg bw. 1,2-Dichloro-4- nitrobenzene causes the formation of methemoglobin. ... 1,2-Dichloro-4-nitrobenzene gave no skin irritation effects when tested for 4 hours under semiocclusive conditions ... and showed slightly irritating effects, which disappeared within 72 hours under occlusive conditions ... 1,2-Dichloro-4-nitrobenzene is slightly irritating to the eyes /but/ ... was not found to induce dermal sensitization ... . In addition, 1,2-dichloro-4-nitrobenzene was not found to induce dermal sensitization in humans in a limited study. The main targets identified in animal studies after repeated oral administration as well as after inhalation exposure are the hematological system and in addition the kidneys after oral application and the liver after inhalation. From a 28- day oral study ... a NOAEL of 4 mg/kg bw/day was derived. The NOAEL following subchronic inhalation exposure study of limited validity (limited documentation) was 0.4 mg/cu m (4 hours per day). Changes in hematological parameters (e.g. methemoglobinaemia, Heinz bodies) are the main target in the only available report on exposure of workers. As these findings relate to mixed exposures they cannot be clearly attributed to 1,2-dichloro-4-nitrobenzene, but would be plausible, because they were also observed in animal experiments. In the recent open literature reports of human poisoning could not be identified. 1,2-Dichloro-4-nitrobenzene exhibits mutagenic activity in Salmonella typhimurium but not in the HPRT test in Chinese Hamster Ovary (CHO) cells. 1,2-Dichloro-4-nitrobenzene induced chromosomal aberrations in V79 cells with metabolic activation only at the highest concentration, which was cytotoxic. In insects (Drosophila melanogaster) 1,2-dichloro-4-nitrobenzene revealed no mutagenic activity in the SLRL-test after application over 3 days with slight increased toxicity, but revealed mutagenic activity following a single ip injection of a clearly toxic dose. 1,2-Dichloro-4-nitrobenzene showed no clastogenic activity in vivo in a chromosomal aberrations test with rats. Overall in non-toxic doses, there was no evidence for genotoxicity in vivo under the conditions tested. Studies dealing specifically with toxicity to reproduction were not identified. The subacute study with 1,2-dichloro-4- nitrobenzene yielded no damage of the reproductive organs in rats despite clear systemic toxicity up to the maximum tolerated dose of 100 mg/kg bw. 1,2-Dichloro-4-nitrobenzene commercial grade (85% 1,2-dichloro-4-nitrobenzene and 15% 1,2-dichloro-3- nitrobenzene) caused effects on development at maternally toxic doses probably due to methemoglobinemia in dams and fetuses. A significant dose-response trend for variations (dilated ureters) was seen in the fetuses of the >= 30 mg/kg bw/day-groups and significant reduced body weight gain of dams at dose levels of 30 mg/kg bw/day on gd 6-10 with an even stronger effect at 100 mg/kg bw/day. Thus, 10 mg/kg bw/day was determined as the NOAEL for maternal and developmental toxicity. Environment: ... Concerning the acute toxicity of 1.2-dichloro-4-nitrobenzene towards aquatic species reliable experimental results of tests with fish, Daphnia, and algae are available. The acute toxicity determined for fish (Leuciscus idus) was of 3.1 mg/L (48 hr LC50) ... and Daphnia (Daphnia magna) of 3 mg/L (24 hr-EC50) ... . In the growth inhibition test with algae (Scenedesmus obliquus) the value 5.8 mg/L was achieved after 48 hr (48 hr-ErC50)... . For the algae Chlorella fusca a value of 0.32 mg/L was found after 24 hr (24 hr-ErC50). In a chronic (21 d) study with Daphnia magna a NOEC of 0.025 mg/L was determined for the most sensitive endpoint reproduction rate. An ErC10 > 0.1 mg/L was reported for the algae Scenedesmus subspicatus after 48 hours. For terrestrial organisms the lowest measured 6d-EC50 was 27 mg/L for the plant Phaseolus aureus. Applying an assessment factor of 50 to the lowest available chronic value of 25 ug/L (21d reproduction in D. magna), a PNECaqua of 0.5 ug/lL is obtained. |
| 生態毒性抜粋 | /AQUATIC SPECIES/ In a reproduction (21 d) study with Daphnia magna performed in a semistatic system in closed vessels /the authors/ found a NOEC of 0.025 mg/L for the most sensitive endpoint reproduction rate. The stability of the test substance concentration was confirmed by analytical monitoring. |
| Signs and Symptoms | Cough.Redness. |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. The substance may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment. |
| Soil Adsorption/Mobility | An experimentally determined mean Koc value of 393 for 3,4-dichloronitrobenzene was reported using 4 silt loam soils(1). A log Koc value of 2.62 was reported following adsorption studies using sediment from the Yangste River in China(2), corresponding to a Koc of 390(SRC). According to a classification scheme(3), these Koc values suggest that 3,4-dichloronitrobenzene is expected to have moderate mobility in soil. Using a modified organo montmorillonite clay from Jiangning Jinagsu Province, China, a log Koc of 3.76 was determined(3), corresponding to a Koc of 5,754(SRC). |
| TSCA Test Submissions | 3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute oral toxicity. The test substance was administered orally to 10 rats (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Signs of toxicity included weakness (moderate to very weak), labored respiration, cyanosis, dark eyes, and prostration. Time of death was between 45 minutes and 2 days. The approximate LD50 was determined to be between 1600 and 3200 mg/kg b.w. The test substance was determined to be slightly toxic.3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute intraperitoneal toxicity. The test substance was administered intraperitoneally to 10 rats (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Signs of toxicity included weakness (moderate to very weak), labored respiration, cyanosis, dark eyes, and prostration. Time of death was between 2 hours and 1 day. The approximate LD50 was determined to be between 400 mg/kg b.w. The test substance was determined to be moderately toxic.3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute oral toxicity. The test substance was administered orally to 10 mice (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Clinical signs included weakness (normal to very weak), decreased activity, slow respiration, cyanosis, dark eyes, slight tremor, prostration, and yellow-orange urine. Time of death was 1 day. The approximate LD50 was determined to be between 800-1600 mg/kg b.w. The test substance was determined to be slightly toxic.3,4-Dichloronitrobenzene (CAS# 99-54-7) was evaluated for acute intraperitoneal toxicity. The test substance was administered intraperitoneally to 10 mice (sex and species not specified) at a dose range of 200-3200 mg/kg body weight. Clinical signs included weakness (normal to very weak), decreased activity, slow respiration, cyanosis, dark eyes, slight tremor, prostration, and yellow-orange urine. Time of death was between 4-1/2 hours and 1 day. The approximate LD50 was determined to be between 400-800 mg/kg b.w. The test substance was determined to be moderately toxic.For more TSCA Test Submissions (Complete) data for 3,4-DICHLORONITROBENZENE (14 total), please visit the HSDB record page. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ In a study with 10 female subjects the single dermal application of a 10 % solution of 1,2-dichloro- 4-nitrobenzene in acetone followed by a challenge with a 10 or 0.01 - 1 % solution in acetone on day 28 and 49 caused no skin sensitization./BIOMONITORING/ 3,4-Dichloronitrobenzene, like other nitro and amino aromatics, is responsible for methemoglobin formation in humans. Levels of 10 mg/L of 3,4-dichloronitrobenzene metabolites in human urine may be considered to be warning levels of overexposure. |
| 水環境危害等級（WGK） | 3 |
| TSCA 収載状態 | TSCA listed |
| RTECS 番号 | CZ5250000 |
| 輸送番号（UN） | 2811 |
| 毒性 | LD50 orally in Rabbit: 643 mg/kg LD50 dermal Rat > 2000 mg/kg |
| PRTR法 | 第一種指定化学物質 |
| 税関コード | 29049085 |
| 危険文句（R） | 22-36-43-51/53 |
| 化審法 | (3)-455 |
| 安衛法 | 変異原性物質 |
| 危険表示 | Xn,N |
| 安全措置（S） | 26-36/37-61-39-24/25 |
| 危険等級 | 9Acute Tox. 4 OralEye Irrit. 2Skin Sens. 1 |
| 包装等級 | III |
| 自然発火温度 | 420 °C |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 99-54-7(Hazardous Substances Data) |
用途
用途
医薬?農薬?染料?顔料中間体
用途
有機合成原料。
一般的な説明
Colorless crystals or light beige solid.
製法・合成法
調製方法
Nitration of 1,2-dichlorobenzene with mixed acid at 35 – 60 ℃ results in a mixture of 3-nitro (10 %) and 4-nitro (90 %) isomers, which are separated by crystallization. A more expensive process (two stages from chlorobenzene) is based on chlorination of molten 4-chloronitrobenzene (90 – 100 ℃) by a process similar to that used for 3- chloronitrobenzene production. Chlorination has the advantage of giving a pure product, but it cannot be used if the isomeric 1,2-dichloro-3-nitrobenzene is also required.
純化方法
Crystallise it from absolute EtOH. [Beilstein 5 IV 726.]