HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
1-Chlor-3-nitrobenzol
mncb · 1-CHLORO-3-NITROBENZENE · 3-CHLORONITROBENZENE · M-NITROCHLOROBENZENE · 3-NITROCHLOROBENZENE · M-CHLORONITROBENZENE · 1-chloronitrobenzene · Metachloronitrobenzene
Identifikatoren & physikalische Daten
| CAS No. | 121-73-3 |
|---|---|
| Summenformel | C6H4ClNO2 |
| Durchschnittliche Molmasse | 157,55 g/mol |
| Monoisotopische Masse | 156,99305605 g/mol |
| SMILES | O=[N+]([O-])c1cccc(Cl)c1 |
| InChIKey | KMAQZIILEGKYQZ-UHFFFAOYSA-N |
| PubChem CID | 8489 |
| ChEMBL | CHEMBL166812 |
| ChEBI | CHEBI:82420 |
| EC No. | 204-496-1 |
| DTXSID | DTXSID4021971 |
| Lokaler Name | 1-Chlor-3-nitrobenzol |
Chemische & physikalische Eigenschaften
| XLogP | 2,5 |
|---|---|
| Polarare Oberfläche (TPSA) | 45,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 134 |
| Stoffklassen | Nitrogen Compounds -> Nitros, Aromatic |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | log Kow = 2.41 |
| Dichte | 1.343 (NTP, 1992) - Denser than waterwill sink1.534 at 20 °C/4 °C1.3 g/cm³1.534 @ 20°C1.534 g/mL at 25 °C(lit.) |
| Color/Form | Pale-yellow orthorhombic prisms from alcohol |
| Löslichkeit | Insoluble (NTP, 1992)Sparingly sol in cold alcoholfreely soluble in hot alcohol, chloroform, ether, carbon disulfide, and glacial acetic acidSoluble in most organic solventsIn water, 0.273 g/L at 20 °CSolubility in water at 20 °C: very pooralcohol: freely soluble (hot)(lit.) |
| Flammpunkt | 261 °F (NFPA, 2010)127 °C261 °F (127 °C) (Closed cup)103 °C c.c.218 °F |
| Siedepunkt | 455 to 457 °F at 760 mmHg (NTP, 1992)236 °C at 760 mm Hg236 °C @760 [mm Hg]236 °C(lit.) |
| Schmelzpunkt | 115 °F (NTP, 1992)46 °CLiquid molar volume = 0.117 cu m/kmolIG Heat of Formation = 3.72X10+7 J/kmolHeat of Fusion at melting point = 2.078X10+7 J/kmol44 °C43-47 °C(lit.) |
| Dampfdichte | Relative vapor density (air = 1): 5.44 |
| Dampfdruck | 0.09 [mmHg]0.097 mm Hg at 25 °CVapor pressure, Pa at 20 °C: 50.097 [mm Hg] @25 °C1.9Pa at 25℃ |
| Surface Tension | 4.37X10-2 N/m at 317.65 deg K |
| Brechungsindex | 1.5545 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Aggregatzustand | powder to lump to clear liquid |
| Farbe | White or Colorless to Yellow |
| pH | 7 (0.26g/l, H2O, 20℃) |
| Merck | 14,2151 |
| BRN | 1907947 |
| Henry-Konstante | 1.4×100 mol/(m3Pa) at 25℃, Chao et al. (2017) |
| Stabilität | Stable. Incompatible with strong oxidizing agents, strong acids, strong reducing agents. |
| LogP (Verteilungskoeffizient) | 2.49 |
| CAS Datenbank | 121-73-3(CAS DataBase Reference) |
| NIST chemische Informationen | Benzene, 1-chloro-3-nitro-(121-73-3) |
| EPA chemische Informationen | m-Chloronitrobenzene (121-73-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (43%): Toxic if swallowed [Danger Acute toxicity, oral]P203, P260, P261, P262, P264, P270, P271, P272, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P316, P318, P319, P321, P330, P333+P317, P361+P364, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 86 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzene, 1-chloro-3-nitro-Status: Cease Manufacture Update: 13-12-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/176421-Chloro-3-nitrobenzene: Does not have an individual approval but may be used under an appropriate group standard |
| DOT-Kennzeichnung | Poison |
| Brandgefahren | Flash point data for this chemical are not available. It is probably combustible. (NTP, 1992)Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air. |
| Gesundheitsgefahren | SYMPTOMS: Symptoms of exposure to this compound may include cyanosis from methemoglobinemiaand blood changes. |
| Gefahrenübersicht | Danger of cutaneous absorption[MAK] A corrosive substance that can cause injury to the skin, eyes, and respiratory tractCan induce methemoglobinemiaOther potential effects are skin sensitization, kidney and liver damage, CNS depression, and chemical pneumonitis[HSDB] An irritant[MSDSonline] |
| Reaktive Gruppe | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| UN-Einstufung | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | European Chemicals BureauIUCLID Dataset, 1-chloro-3-nitrobenzene (CAS # 121-73-3) (2000 CD-ROM edition). Abstracts information on usage patterns, toxicity, and ecotoxicity provided to the European Union by industry. |
| Reactivity Profile | 3-CHLORONITROBENZENE can react with oxidizing materials. (NTP, 1992). |
| Chemical Dangers | Decomposes on burning. This produces toxic and corrosive fumes including nitrogen oxides, chlorine (see ICSC 0126), hydrogen chloride (see ICSC 0163) and phosgene (see ICSC 0007). This generates fire and explosion hazard. The substance is a strong oxidant. It reacts with combustible and reducing materials. |
| Flammable Limits | Lower flammable limit: 1.4% by volumeUpper flammable limit: 8.7% by volume |
| Physical Dangers | Dust explosion possible if in powder or granular form, mixed with air. |
| Brandbekämpfung | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)Use water spray, foam, carbon dioxide. |
| Erste-Hilfe-Maßnahmen | Fresh air, rest. Refer for medical attention.Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .Rinse with plenty of water for several minutes (remove contact lenses if easily possible).Rinse mouth. Refer immediately for medical attention. |
| Erste Hilfe | 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. |
| Sichere Lagerung | Separated from combustible substances, reducing agents and food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing. |
| Brandbekämpfungsverfahren | Water may cause foaming or frothing. Use water spray, dry chemical, foam, or carbon dioxide. /Chloronitrobenzenes/If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use foam, dry chemical, or carbon dioxide. /Chloronitrobenzenes, meta, solid/ |
| Lagerbedingungen | Store in a cool, dry, well ventilated location. Separate from alkalies and oxidizing materials. /Chloronitrobenzenes/ |
| Reinigungsverfahren | Environmental considerations-land spill: Dig a pit, pond, lagoon, holding area to contain liquid or solid material. /SRP: If time permits, pits, ponds, lagoons, soak holes, or holding areas should be sealed with an impermeable flexible membrane liner./ Cover solids with a plastic sheet to prevent dissolving in rain or fire fighting water. Dike surface flow using soil, sand bags, foamed polyurethane, or foamed concrete. Absorb bulk liquid with fly ash, cement powder, or commercial sorbents. /Chloronitrobenzenes, meta, solid/Environmental considerations-water spill: Use natural barriers or oil spill control booms to limit spill travel. Use natural deep water pockets, excavated lagoons, or sand bag barriers to trap material at bottom. Remove trapped material with suction hoses. /Chloronitrobenzenes, meta, solid/Environmental considerations-air spill: Apply water spray or mist to knock down vapors. /Chloronitrobenzenes, meta, solid/ |
| Freisetung ohne Brand | 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 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% 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 60-70% 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. |
| Entsorgungsverfahren | 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.A novel membrane bioreactor has been used to extract and biodegrade nitrobenzene and 3-chloronitrobenzene from an industrial wastewater arising in 3-chloronitrobenzene manufacture. ... |
| Verschüttetes entsorgen | 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 | Personnel protection: Avoid breathing vapors. Keep upwind. ... Avoid bodily contact with the material. ... Do not handle broken packages unless wearing appropriate personal protective equipment. Wash away any material which may have contacted the body with copious amounts of water or soap and water. /Chloronitrobenzenes, meta, solid/If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard. Use water spray to knock-down vapors. /Chloronitrobenzenes, meta, solid/SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.Evacuation: If material leaking (not on fire) consider evacuation from downwind area based on amount of material spilled, location and weather conditions. /Chloronitrobenzenes, meta, solid/ |
| Isolation and Evacuation | Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: |
| Ökotoxizitätswerte | EC50 Daphnia magna 26 mg/L for 48 hr. /Conditions of bioassay not specified in source examined/LC50Species: Daphnia magna (Water flea)Conditions: freshwater, staticConcentration: 26000 ug/L for 48 hr /99.7% purity/Species: Daphnia magna (Water flea, <24 hr old)Conditions: freshwater, static, 25 °C, pH 8.2, hardness 250 mg/L CaCO3, dissolved oxygen >6.5 mg/LConcentration: 20000 ug/L for 48 hr (95% confidence interval: 10000-32000 ug/L) />98% purity/Concentration: 2000 ug/L for 21 days (95% confidence interval: 1700-2300 ug/L) />98% purity/For more Ecotoxicity Values (Complete) data for 1-CHLORO-3-NITROBENZENE (11 total), please visit the HSDB record page. |
| Umweltverhalten | TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 310(SRC), determined from a structure estimation method(2), indicates that 1-chloro-3-nitrobenzene is expected to have moderate mobility in soil(SRC). Volatilization of 1-chloro-3-nitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.4X10-5 atm-cu m/mole(3). 1-Chloro-3-nitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an extrapolated vapor pressure of 0.097 mm Hg at 25 °C(4). The biodegradation half-life of 1-chloro-3-nitrobenzene was >64 days in solutions using microorganisms derived from a soil inoculum(5).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 310(SRC), determined from a structure estimation method(2), indicates that 1-chloro-3-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 1.4X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 56 hours and 30 days, respectively(SRC). According to a classification scheme(5), BCF values of 77-91 measured in fish(6), suggests bioconcentration in aquatic organisms is moderate(SRC). Screening tests using river water(7) suggest biodegradation of 1-chloro-3-nitrobenzene proceeds slowly under aerobic conditions in water. Degradation may proceed more quickly under anaerobic conditions given a biodegradation half-life of 3.2 days in anaerobic estuarine sediment(8). 1-Chloro-3-nitrobenzene was shown to undergo photolysis in pure water and river water when exposed to natural outdoor sunlight(9), suggesting photolysis in sunlit surface water is possible(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chloro-3-nitrobenzene , which has a vapor pressure of 0.097 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1-chloro-3-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 134 days(SRC), calculated from its rate constant of 1.2X10-13 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1-Chloro-3-nitrobenzene was shown to undergo photolysis in pure water and river water when exposed to natural outdoor sunlight(4), suggesting photolysis in air is possible(SRC). |
| Unerwünschte Wirkungen | 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. |
| Expositionspfade | The substance can be absorbed into the body by inhalation, through the skin and by ingestion. |
| Signs and Symptoms | Blue lips, fingernails and skin. Dizziness. Headache. Nausea. Confusion. Convulsions.MAY BE ABSORBED! See Inhalation.Redness.Blue lips, fingernails and skin. See Inhalation. |
| Effluent Concentrations | 1-Chloro-3-nitrobenzene was reported in industrial wastewater from the organics and plastics industry at unknown concentrations and locations(1). 1-Chloro-3-nitrobenzene was detected in advanced waste treatment effluent from Pomona, CA in June 1975 at an unknown concentration(2). |
| ICSC Environmental Data | The substance is toxic to aquatic organisms. 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-chloro-3-nitrobenzene can be estimated to be 310(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1-chloro-3-nitrobenzene is expected to have moderate mobility in soil(SRC). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Corrosive. Causes severe eye & skin burns. Irritating to skin, eyes, & respiratory system. May cause cyanosis & pulmonary edema. /Chloronitrobenzenes//SIGNS AND SYMPTOMS/ 1-Chloro-3-nitrobenzene...is capable of producing methemoglobinemia when absorbed./SIGNS AND SYMPTOMS/ Three out of 4 cases of cyanosis will exhibit classical blue or ashen-grey appearance but only 1/3 of the victims will complain of anoxia symptoms (headache, fatigue, nausea, vertigo, chest pain, numbness, abdominal pain, aching, palpitation, aphonia, nervousness, air hunger and irritational behavior). /Nitro-compounds, aromatic//SIGNS AND SYMPTOMS/ Experience with human exposure: in chloronitrobenzene poisoning cardiac complications appear to be more frequent and more serious than in aniline poisoning and gastrointestinal irregularities (anacidity) also appear to be quite common (no further data, isomer(s) of chloronitrobenzene not specified). /Chloronitrobenzenes/For more Human Toxicity Excerpts (Complete) data for 1-CHLORO-3-NITROBENZENE (7 total), please visit the HSDB record page. |
| Fish/Seafood Concentrations | 1-Chloro-3-nitrobenzene was detected in Mississippi River buffalo fish at unknown concentrations from a localized 150 mile section of the river extending from St. Louis, MO to Cape Girardeau, MO. 1-Chloro-3-nitrobenzene at concentrations of 0.057 ppm were found in carp and sucker fish within the same section of the Mississippi River(1). |
| Artificial Pollution Sources | 1-Chloro-3-nitrobenzene's production and use as an intermediate in preparing dyes(1), may result in its release to the environment through various waste streams(SRC). Manufacturers that produce o- and p-chloronitrobenzene via nitration of chlorobenzene are expected to produce small amounts of 1-chloro-3-nitrobenzene, a minor product of this reaction (0.9%)(2). 1-Chloro-3-nitrobenzene may be formed in drinking water during chlorination if nitrobenzene is present and may also be formed in small quantities during chlorination of sewage effluent when nitrobenzene is present(2). Chlorobenzene is converted to 1-chloro-3-nitrobenzene plus various chlorophenols when exposed to UV rays in the presence of nitrogen oxides in air(3). These indirect sources may result in its release to the environment(SRC). |
| Environmental Biodegradation | AEROBIC: 1-Chloro-3-nitrobenzene was tested for biodegradability using the OECD, river die-away, and Pitter teststhe half-life for 1-chloro-3-nitrobenzene was much greater than four weeks for these tests using both unadapted and adapted inoculum(1). A lack of significant ring cleavage by day 64, as measured by UV spectroscopy, showed that 1-chloro-3-nitrobenzene at 10 ug/mL did not degrade readily in aqueous suspensions of Niagara silt loam(2). This analytical method was not selective enough however, to determine whether biotransformations not involving aromatic ring cleavage may have taken place(2). Information from studies to determine the effectiveness of various drinking water purification methods in the Netherlands suggests that 1-chloro-3-nitrobenzene may be biodegraded in soil(3). The removal of 1-chloro-3-nitrobenzene from bank-filtered water that was observed in these studies, may have been due partly to biodegradationhowever, the contribution of other processes such as adsorption was not determined. In an earlier study, 1-chloro-3-nitrobenzene was measured in bank-filtered Rhine River water retained for a time of >1 year(4). The biodegradation half-life of 1-chloro-3-nitrobenzene was >64 days in solutions using microorganisms derived from a soil inoculum(5).ANAEROBIC: The rate constant for the anaerobic biodegradation of 1-chloro-3-nitrobenzene in sediment obtained from the Tsurumi River, Japan was 0.216 days-1, which corresponds to a half-life of 3.2 days(1). |
| Landesrichtlinien für Trinkwasser | (FL) FLORIDA 250 ug/L |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | UN 1578 6.1/PG 2 |
| Zollcode | 29049085 |
| RTECS-Nr. | CZ0940000 |
| R-Sätze (R) | 22-50/53-23/24/25 |
| Toxizität | mouse,LD50,oral,380mg/kg (380mg/kg),Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 25(8), Pg. 50, 1981. |
| Gefahrensymbole | Xn,N,T |
| Sicherheitshinweise (S) | 22-24/25-60-61-45-38-36/37/39-28A |
| Gefahrenklasse | 6.1 |
| Verpackungsgruppe | II |
| Gefahrstoffdaten | 121-73-3(Hazardous Substances Data) |
| Selbstentzündungstemperatur | 500 °F |
Anwendungen & Verwendung
Verwenden
Intermediate for dyes. 1-Chloro-3-nitrobenzene was used in the preparation of aromatic azo compounds using gold (Au) nanoparticles supported on TiO2 as a catalyst. It was also used as surrogate standard to evaluate the removal of 2,4-dinitrotoluene from contaminated soils using enhanced electrokinetic remediation.