Huagongshe화공사 화학 정보 인쇄 보고서 · 연구 참고용
1,4-디클로로-2-니트로벤젠
1,4-디클로로-2-나이트로벤젠 · 1,4-디클로로-2-니트로벤젠 · 2,5-디클로로-1-니트로벤젠 · 2,5-다이클로로나이트로벤젠 · 1,4-다이클로로-2-나이트로벤젠 · 1,4-다이클로로-3-나이트로벤젠 · 1-나이트로-2,5-다이클로로벤젠 · 2,5-다이클로로-1-나이트로벤젠
식별자 및 물리적 특성
| CAS No. | 89-61-2 |
|---|---|
| 분자식 | C6H3Cl2NO2 |
| 평균 분자량 | 192 g/mol |
| 단동위원소 질량 | 190.9540837 g/mol |
| SMILES | O=[N+]([O-])c1cc(Cl)ccc1Cl |
| InChIKey | RZKKOBGFCAHLCZ-UHFFFAOYSA-N |
| PubChem CID | 6977 |
| ChEMBL | CHEMBL354761 |
| EC No. | 201-923-3 |
| DTXSID | DTXSID7052602 |
| 현지명 | 1,4-디클로로-2-니트로벤젠 |
화학 및 물리적 성질
| XLogP | 2.9 |
|---|---|
| 극성 표면적 | 45.8 |
| 수소 결합 공여자 수 | 0 |
| 수소 결합 수용자 수 | 2 |
| 회전 가능 결합 수 | 0 |
| 무거운 원자 수 | 11 |
| 형식 전하 | 0 |
| 복잡도 | 159 |
| pH | pH = 6.9 (80 mg/L water) at 20 °C |
| LogP(분배 계수) | log Kow = 3.092.93 |
| 밀도 | 1.669 at 22 °CDensity: 1.479 g/cu cm at 75 °C1.67 g/cm³Relative density of the vapour/air-mixture at 20 °C (air = 1): 1.001,442 g/cm3 |
| Color/Form | Plates or prisms from alcohol, plates from ethyl acetate |
| 용해도 | In water, 95 mg/L at 25 °CIn water, 92.1 mg/L at 20 °CSoluble in ethanol, ether, benzene, carbon disulfideslightly soluble in carbon tetrachlorideSolubility in water, g/100ml at 20 °C: 0.01 (very slightly soluble)0.083g/L |
| 인화점 | 135 °C>230 °F |
| 끓는 점 | 267 °C261 °C |
| Decomposition | When heated to decomposition it emits very toxic fumes of /hydrogen chloride and nitrogen oxides/. |
| 녹는점 | 56 °C55 °C52-54 °C(lit.) |
| 증기 밀도 | Relative vapor density (air = 1): 6.66.6 (vs air) |
| 증기압 | 0.00505 [mmHg]0.00383 mm Hg at 25 °CVapor pressure, Pa at 25 °C: 0.5<0.1 mm Hg ( 25 °C) |
| Surface Tension | 6.6 (Air = 1) |
| 굴절률 | 1.4390 (estimate) |
| 저장 조건 | Store below +30°C. |
| 물리적 상태 | solid |
| 색상 | 옅은 노랑 |
| 폭발한계 | 2.4-8.5%(V) |
| 용해도 | 물, 에탄올, 에테르, 벤젠, 이황화탄소에 용해됩니다. 사염화탄소에 약간 용해됩니다. |
| BRN | 778109 |
| 헨리 상수 | 8.2×10-1 mol/(m3Pa) at 25℃, Altschuh et al. (1999) |
| InChI | 1S/C6H3Cl2NO2/c7-4-1-2-5(8)6(3-4)9(10)11/h1-3H |
| InChIKey | RZKKOBGFCAHLCZ-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1cc(Cl)ccc1Cl |
| LogP(분배 계수) | 2.87 at 25℃ |
| NIST | Benzene, 1,4-dichloro-2-nitro-(89-61-2) |
| EPA | 2,5-Dichloronitrobenzene (89-61-2) |
화학적 성질
yellow flakes
안전 및 규제
| GHS 분류 | DangerH350: May cause cancer [Danger Carcinogenicity]P203, P280, P318, P405, and P501 (click each P-code to see the statement)This chemical does not meet GHS hazard criteria for 1.1% (1 of 94) of reports. |
|---|---|
| 규제 정보 | Chemical: Benzene, 1,4-dichloro-2-nitro-Hazard Traits - CarcinogenicityAuthoritative List - EC Annex VI CMRs - Cat. 1BIARC Carcinogens - 2BProp 65Report - regardless of intended function of ingredient in the productTP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.Status: Active Update: 28-06-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/175481,4-Dichloro-2-nitrobenzene: Does not have an individual approval but may be used under an appropriate group standard |
| 기타 안전 정보 | Evaluation - Benzene, 1,4-dichloro-2-nitro- (2,5-dichloronitrobenzene) |
| 화재 위험 | Combustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| 유해성 요약 | No listed effects of short-term or long-term exposure (health effects have not been fully investigated)[ICSC] Can possibly induce methemoglobinemiaCan be absorbed through skinNot a skin or eye irritant in rabbitsNot sensitizing in guinea pig maximization testsNo mortalities in rats exposed by inhalation to 47.6 mg/m3 for 7 hoursIncreased liver weight (accompanied by hepatocellular hypertrophy), damage to the forestomach, increased bilirubin levels, and adverse male reproductive effects (depressed spermatogenesis) observed in 28-day oral study of ratsCyanosis and methemoglobin formation observed in cats[IUCLID] A mild skin and strong eye irritantMay induce methemoglobinemiaHarmful by ingestion and skin absorption[Sigma-Aldrich MSDS] See 3,4-Dichloronitrobenzene. |
| UN 분류 | UN Hazard Class: 6.1UN Pack Group: II |
| Chemical Dangers | Decomposes on heating. This produces toxic and corrosive fumes including hydrogen chloride (see ICSC 0163) and nitrogen oxides (see ICSC 0282). Reacts with strong oxidants and bases. |
| Packaging and Labelling | Do not transport with food and feedstuffs. |
| Hazard Classes and Categories | Acute Tox. 4 (98.9%)Skin Sens. 1 (43.6%)Eye Irrit. 2 (93.6%)Muta. 2 (46.8%)Aquatic Chronic 2 (53.2%)Aquatic Chronic 3 (42.6%)Acute toxicity (ingestion) - category 4Eye irritation - category 2Specific target organ toxicity (repeated exposure) - category 2Carcinogenicity - category 1BAcute toxicity (Oral) - Category 4Carcinogenicity - Category 2Reproductive toxicity - Category 2Specific target organ toxicity - Single exposure - Category 1 (blood system), Category 3 (narcotic effects)Specific target organ toxicity - Repeated exposure - Category 1 (blood system), Category 2 (nervous system, liver, kidney)Hazardous to the aquatic environment (Acute) - Category 1Hazardous to the aquatic environment (Long-term) - Category 1Skin corrosion/irritation - Category 3Serious eye damage/eye irritation - Category 2ASkin sensitization - Category 1Specific target organ toxicity - Repeated exposure - Category 1 (blood system), Category 2 (nervous system, liver, testis) |
| Explosive Limits and Potential | Explosive limits , vol% in air: 2.4-8.5 |
| Skin, Eye, and Respiratory Irritations | A skin and eye irritant.1,4-Dichloro-2-nitrobenzene is mildly irritating to eyes and non-irritating to skin. |
| 소화 | Use water spray, dry powder, foam, carbon dioxide. |
| 응급 조치 | Fresh air, rest.Rinse and then wash skin with water and soap. Refer for medical attention .Rinse with plenty of water (remove contact lenses if easily possible).Rinse mouth. Refer for medical attention . |
| 안전 보관 | Separated from bases, strong oxidants and food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. |
| 처리 방법 | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air qualitypotential migration in soil or watereffects on animal and plant lifeand conformance with environmental and public health regulations. |
| 누출 처리 | Personal protection: particulate filter respirator adapted to the airborne concentration of the substance, protective clothing, protective gloves and face shield. Do NOT let this chemical enter the environment. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations. |
| Preventive Measures | SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place. |
| Eye Prevention | Wear safety spectacles. |
| Fire Prevention | NO open flames. |
| Inhalation Risk | A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered. |
| Skin Prevention | Protective gloves. |
| Exposure Prevention | PREVENT DISPERSION OF DUST! STRICT HYGIENE! |
| Ingestion Prevention | Do not eat, drink, or smoke during work. |
| 생태독성 수치 | EC50Species: Chlorella pyrenoidosa (Green Algae) exponential growth phase, 2 X10+8 cells/mLConditions: freshwater, static, 25 °C, pH 6.6Concentration: 2100 ug/L for 96 hr (95% confidence interval: 1500-2800 ug/L)Effect: growth, general />98% purity formulation/LC50Species: Daphnia magna (Water Flea) age <24 hrConditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3. dissolved oxygen >6.5 mg/LConcentration: 11000 ug/L for 48 hr (95% confidence interval: 5600-18000 ug/L) />98% purity formulation/Concentration: 3800 ug/L for 21 days (95% confidence interval: 3600-4000 ug/L) />98% purity formulation/Species: Poecilia reticulata (Guppy) age 3-4 weeksConditions: freshwater, static, 25 °C, pH 8.2, hardness 250 mg/L CaCO3Concentration: 4900 ug/L for 14 days />98% purity formulation/For more Ecotoxicity Values (Complete) data for 1,4-Dichloro-2-nitrobenzene (6 total), please visit the HSDB record page. |
| 환경 거동 | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 590(SRC), determined from a structure estimation method(2), indicates that 1,4-dichloro-2-nitrobenzene is expected to have low mobility in soil(SRC). Volatilization of 1,4-dichloro-2-nitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.5X10-5 atm-cu m/mole(3). 1,4-Dichloro-2-nitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00383 mm Hg at 25 °C(4). 1,4-Dichloro-2-nitrobenzene absorbs UV light above 290 nm and will photodegrade in sunlight(4). Utilizing the Japanese MITI test, 4% of the theoretical BOD was reached in four weeks(5) indicating that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 590(SRC), determined from a structure estimation method(2), indicates that 1,4-dichloro-2-nitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.5X10-5 atm-cu m/mole at 25 °C(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.4 and 36 days, respectively(SRC). According to a classification scheme(5), observed BCF values of 18-118, measured in carp and rainbow trout(6,7), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). 1,4-Dichloro-2-nitrobenzene has an epilson of 0.00126 at 300 nm in aqueous solution(8) which indicates the compound may be susceptible to direct photolysis(SRC)an approximated quantum yield of 0.01 can be used to estimate a half-life of 34 days in a model sunlit body of water with a 500 cm depth(2). In an aqueous hydrolysis test (OECD Test guideline 111), benzene, 1,4-dichloro-2-nitro was stable to abiotic hydroylsis at pHs 4, 7 and 9 at 25 °C(8). Utilizing the Japanese MITI test, 4% of the theoretical BOD was reached in four weeks(6) indicating that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-dichloro-2-nitrobenzene, which has a vapor pressure of 0.00383 mm Hg at 25 °C(2), expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-dichloro-2-nitrobenzene 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 320 days(SRC), calculated from its rate constant of 5X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,4-Dichloro-2-nitrobenzene absorbs UV light above 290 nm and therefore is photodegraded in sunlight(2). |
| 유해 작용 | 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 effectIARC Carcinogen - Class 3: Chemicals are not classifiable by the International Agency for Research on Cancer. |
| 노출 경로 | The substance can be absorbed into the body by ingestion and through the skin. |
| Average Daily Intake | For indirect exposure to 1,4-dichloro-2-nitrobenzene via the environment, the daily intake through drinking water is estimated to be 2.6X10-5 mg/kg/day and through fish is calculated as 1.2X10-3 mg/kg/day(1). |
| 생태독성 발췌 | /AQUATIC SPECIES/ Following the exposure of algae (Chlorella pyrenoidosa) for 96 hours to 2.1 mg/L, 50% inhibition of growth has been observed... For water fleas (Daphnia magna), 48-hr EC50 value (immobilization) amounts to 11 mg/L and the 21-day EC50 value to 3.8 mg/L. In a semi-static 21-day reproduction test the lowest concentrations at which the population growth rate and mean length of the animals significantly (p<0.01) decreased were 1.8 mg/L and 3.2 mg/L respectively. For fish (Leuciscus idus), the value of acute toxicity (96-hr LC50) in an open system under semi-static conditions is 6.3 mg/L and the corresponding value (48-hr LC50) in a closed system under static conditions is 4.5 mg/L. The lowest 96-hr LC0 was 3.15 mg/L. In the prolonged fish toxicity test under semi-static conditions a 14 day LC50 value of 4.9 mg/L has been found for Poecilia reticulata./PLANTS/ 1,4-Dichloro-2-nitrobenzene at concentrations > 42.2 mg/L is phytotoxic (6-day EC50reduction in fresh weight) to higher plants (seedlings of cucumber and bean). |
| Animal Concentrations | 1,4-Dichloro-2-nitrobenzene was detected in zebra mussels (Dreissena polymorpha) collected from the Rhine-Meuse delta in 1994 at concentrations of 0.021-0.030 mg/kg wet weight(1). |
| 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 | Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,4-dichloro-2-nitrobenzene can be estimated to be 590(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,4-dichloro-2-nitrobenzene is expected to have low mobility in soil. 1,4-Dichloro-2-nitrobenzene did not leach in column leachate tests designed to assess leaching potential from wastes in landfill sites(3). |
| Human Toxicity Excerpts | /OTHER TOXICITY INFORMATION/ 1,4-Dichloro-2-nitrobenzene is mildly irritating to eyes and non-irritating to skin. When tested in animals the product has been proved to be a non-sensitizerhowever, there are indications of skin sensitization in man. |
| Artificial Pollution Sources | 1,4-Dichloro-2-nitrobenzene's production and use in the manufacture of dyestuff intermediates, pesticides and UV absorbents(1,2) may result in its release to the environment through various waste streams(SRC). |
| 수질 위해 등급(WGK) | 2 |
| TSCA 등재 상태 | TSCA listed |
| RTECS 번호 | CZ5260000 |
| 운송 번호(UN) | UN 3077 9/PG 3 |
| 관세 코드 | 29049085 |
| 위험 문구(R) | 22-36-51/53 |
| 위험 표시 | Xn,N |
| 안전 문구(S) | 26-60 |
| 포장분류 | III |
| 위험 등급 | 9Acute Tox. 4 OralAquatic Chronic 2 |
| 기존화학 물질 | 2008-2-30 |
| 저장 분류 | 11 - Combustible Solids |
| 유해 물질 데이터 | 89-61-2(Hazardous Substances Data) |
제조 및 합성 방법
생산 방법
Nitration of 1,4-dichlorobenzene with mixed acid at 35 – 65 ℃ results in a 98 % yield of essentially pure 2,5-Dichloronitrobenzene.