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Home > Encyclopedia > 1-Chloro-3-nitrobenzene

1-Chloro-3-nitrobenzene

1-Chloro-3-nitrobenzene structure

1-Chloro-3-nitrobenzene 

structure
  • CAS No:

    121-73-3

  • Formula:

    C6H4ClNO2

  • Chemical Name:

    1-Chloro-3-nitrobenzene

  • Synonyms:

    Benzene,1-chloro-3-nitro-;1-Chloro-3-nitrobenzene;3-Nitrochlorobenzene;3-Chloronitrobenzene;3-Chloro-1-nitrobenzene;m-Nitrochlorobenzene;m-Chloronitrobenzene;NSC 5502;3-Nitrophenyl chloride;3-Nitro-1-chlorobenzene;1-Nitro-3-chlorobenzene

  • Categories:

    Organic Chemistry  >  Hydrocarbons and Derivatives

Description

Moist tan or pale yellow crystalline solidPale yellow crystals. Insoluble in water.


3-chloronitrobenzene appears as pale yellow crystals. Insoluble in water. (NTP, 1992)|PALE YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.


3-chloronitrobenzene appears as pale yellow crystals. Insoluble in water. (NTP, 1992)|1-chloro-3-nitrobenzene is a C-nitro compound that is nitrobenzene in which one of the meta- hydrogens has been replced by chlorine. It is a C-nitro compound and a member of monochlorobenzenes.

1-Chloro-3-nitrobenzene Basic Attributes

157.55

157.55

1907947

204-496-1

8XSA3GF8O1

1633

5502

1578

DTXSID4021971

Pale-yellow orthorhombic prisms from alcohol

29049085

Characteristics

45.8

2.41

3-chloronitrobenzene appears as pale yellow crystals. Insoluble in water. (NTP, 1992)

1.534 g/cm3 @ Temp: 20 °C

46 °C

236 °C @ Press: 760 Torr

218 °F

1.5545 (estimate)

H2O: INsoluble ;alcohol: freely soluble (hot)(lit.)

Store below +30°C.

Vapour pressure, Pa at 20°C: 5

Relative vapour density (air = 1): 5.44

Oral-rat LD50:420 mg/kg;Oral-Mouse LD50:380 mg/kg

Combustible in case of open fire; burning produces toxic chloride and nitrogen oxide fumes

1.35e-05 atm-m3/mole|Henry's Law constant = 1.35X10-5 atm-cu m/mol at 25 °C

Heat of fusion: 29.38 cal/g|CAN REACT WITH OXIDIZING MATERIALS|Hydroxyl radical reaction rate constant = 1.20X10-13 cu cm/molec-sec at 25 °C (est)

Insoluble in water.

Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic

3-CHLORONITROBENZENE can react with oxidizing materials. (NTP, 1992).

500 °F (260 °C)|500 °C

-2.82E+9 J/kmol

Lower flammable limit: 1.4% by volume; Upper flammable limit: 8.7% by volume

Dust explosion possible if in powder or granular form, mixed with air.

5.58E+7 J/kmol at melting point at 317.65 deg K

Critical temperature = 742.0 deg K; Critical pressure = 3.98E+6 Pa

Safety Information

II

6.1

UN 1578 6.1/PG 2

2

22-50/53-23/24/25

22-24/25-60-61-45-38-36/37/39-28A

CZ0940000

Xn,N,T

Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives

Stable. Incompatible with strong oxidizing agents, strong acids, strong reducing agents.

P273

H302-H400

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 quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and 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. ...

Reacts with alkalies, oxidizing materials. /Chloronitrobenzenes/

European Chemicals Bureau; IUCLID 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.

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.

|Danger|H301 (40.24%): Toxic if swallowed [Danger Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P310, P301+P312, P302+P352, P304+P340, P308+P313, P311, P312, P314, P321, P322, P330, P333+P313, P361, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 82 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Excerpt from ERG Guide 152 [Substances - Toxic (Combustible)]: As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. SPILL: Increase, in the downwind direction, as necessary, the isolation distance shown above. FIRE: If tank, rail car or tank truck is involved in a fire, ISOLATE for 800 meters (1/2 mile) in all directions; also, consider initial evacuation for 800 meters (1/2 mile) in all directions. (ERG, 2016)

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. STORAGE PRECAUTIONS: You should store this chemical under refrigerated temperatures, and keep it away from oxidizing materials. (NTP, 1992)

MINIMUM PROTECTIVE CLOTHING: If Tyvek-type disposable protective clothing is not worn during handling of this chemical, wear disposable Tyvek-type sleeves taped to your gloves. RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with a combination filter cartridge, i.e. organic vapor/acid gas/HEPA (specific for organic vapors, HCl, acid gas, SO2 and a high efficiency particulate filter). (NTP, 1992)|Wear special protective clothing and positive pressure self-contained breathing apparatus. /Chloronitrobenzenes/

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/

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/

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/

/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Health: Highly toxic, may be fatal if inhaled, swallowed or absorbed through skin. Contact with molten substance may cause severe burns to skin and eyes. Avoid any skin contact. Effects of contact or inhalation may be delayed. Fire may produce irritating, corrosive and/or toxic gases. Runoff from fire control or dilution water may be corrosive and/or toxic and cause pollution. /Chloronitrobenzenes; Chloronitrobenzenes, liquid; Chloronitrobenzenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chloronitrobenzenes; Chloronitrobenzenes, liquid; Chloronitrobenzenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Public Safety: CALL Emergency Response Telephone Number ... . As an immediate precautionary measure, isolate spill or leak area in all directions for at least 50 meters (150 feet) for liquids and at least 25 meters (75 feet) for solids. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. /Chloronitrobenzenes; Chloronitrobenzenes, liquid; Chloronitrobenzenes, solid/|/GUIDE 152: SUBSTANCES - TOXIC (COMBUSTIBLE)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Wear chemical protective clothing that is specifically recommended by the manufacturer. It may provide little or no thermal protection. Structural firefighters' protective clothing provides limited protection in fire situations ONLY; it is not effective in spill situations where direct contact with the substance is possible. /Chloronitrobenzenes; Chloronitrobenzenes, liquid; Chloronitrobenzenes, solid/|For more DOT Emergency Guidelines (Complete) data for 1-CHLORO-3-NITROBENZENE (8 total), please visit the HSDB record page.

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./|The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.|The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Irritating to skin, eyes, & respiratory system. ... /Chloronitrobenzenes/

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.

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.

A harmful concentration of airborne particles can be reached quickly when dispersed, especially if powdered.

The substance is mildly irritating to the eyes. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. The effects may be delayed. Medical observation is indicated.

The substance may have effects on the blood. This may result in the formation of methaemoglobin.

NO open flames.

PREVENT DISPERSION OF DUST! STRICT HYGIENE!

Use local exhaust. Use breathing protection.

Protective gloves. Protective clothing.

Wear safety goggles.

| 2 - Materials that, under emergency conditions, can cause temporary incapacitation or residual injury.| 1 - Materials that must be preheated before ignition can occur. Materials require considerable preheating, under all ambient temperature conditions, before ignition and combustion can occur.| 0 - Materials that in themselves are normally stable, even under fire conditions.

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).

Toxicity

highly toxic

LD50 Mouse oral 390 mg/kg bw|LD50 Rat oral 470 mg/kg bw|LD50 Rat oral 300 mg/kg|LD50 Rat dermal 890 mg/kg, male|For more Non-Human Toxicity Values (Complete) data for 1-CHLORO-3-NITROBENZENE (7 total), please visit the HSDB record page.

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).

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).

The rate constant for the vapor-phase reaction of 1-chloro-3-nitrobenzene with photochemically produced hydroxyl radicals has been estimated to be 1.2X10-13 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 134 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Chloro-3-nitrobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). The irradiation of 1-chloro-3-nitrobenzene from 1 to 5 hours using a xenon arc lamp in air free from nitrogen oxides resulted in the formation of 3-chloro-2-nitrophenol, 3-chloro-6-nitrophenol, and 3-chloro-4-nitrophenol(3). 89% of 1-chloro-3-nitrobenzene irradiated in air in a quartz vessel disappeared with 3.6% of the reaction product as 3-chloro-2-nitrophenol, 1.1% as 3-chloro-6-nitrophenol, and 23% as 3-chloro-4-nitrophenol(3). The irradiation of 1-chloro-3-nitrobenzene in nitrogen without nitrogen oxides present resulted in m-chlorophenol formation(3). In a quartz vessel, 98% of the 1-chloro-3-nitrobenzene disappeared with 12% of the reaction product appearing as m-chlorophenol(3). 1-Chloro-3-nitrobenzene was shown to undergo photolysis in pure water and river water when exposed to natural outdoor sunlight(4).|Natural organic matter (NOM) obtained from groundwaters, four streams draining bog areas, two landfill leachates and two extracts from tree materials) were studied for their ability to reduce 1-chloro-3-nitrobenzene(1). Under reducing conditions and in the presence of natural organic matter (66 mg C/L in aqueous solution, 5 mM H2S, Eh<-0.2 V) 1-chloro-3-nitrobenzene is reduced abiotically mainly to 3-chlorophenylhydroxylamine and 3-chloroaniline. Using NOM from bog water from Hyde County NC, the 2nd order, carbon normalized rate constants for solutions containing 80 uM 1-chloro-3-nitrobenzene were recorded as 8X10-5 L/hr-mg C at pH 5.5, 8.1X10-4 L/hr-mg C at pH 7.2 and 2.2X10-3 L/hr-mg C at pH 8.6(1). The results from this study demonstrate that natural organic matter mediates the reduction of substituted nitroaromatic compounds in reducing environments. It is suggested that quinone-type species play a predominant role in natural organic matter mediated reductions of 1-chloro-3-nitrobenzene(1). Quinoid-type compounds and iron porphyrins were shown to be effective mediators for the reduction of nitroaromatic compounds, including chloronitrobenzenes(2). Reaction conditions are homogeneous aqueous solutions (pH 6.8-7.0, 5 mM H2S) containing reduced sulfur species as bulk electron donors(2). Therefore, the reduction of chloronitrobenzenes in the environment may occur under reducing conditions in the presence of electron transfer mediators(SRC).

77.62|Rainbow trout (Salmo gairdneri) were fed a mixture of 14 different chloronitrobenzenes, including 1-chloro-3-nitrobenzene, and the amount of 1-chloro-3-nitrobenzene present in the fish was measured over 36 days(1). 1-Chloro-3-nitrobenzene was present in trace amounts 3 days following exposure and was not detectable (<5 ug/kg fish) after 8 days. Fish in water containing 800 ng/L of 1-chloro-3-nitrobenzene plus the same mixture of chloronitrobenzenes had BCF values for 1-chloro-3-nitrobenzene of 77 after 5 days to 91 after 36 days with a mean BCF of 78(1). According to a classification scheme(2), these BCF values suggest bioconcentration in aquatic organisms is moderate(SRC).

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).

The Henry's Law constant for 1-chloro-3-nitrobenzene is 1.4X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 1-chloro-3-nitrobenzene is expected to volatilize from water surfaces(2). Based on this Henry's Law constant, the volatilization half-life from a model river (1 m deep, flowing 1 m/sec, wind velocity of 3 m/sec)(2) is estimated as 56 hours(SRC). The volatilization half-life from a model lake (1 m deep, flowing 0.05 m/sec, wind velocity of 0.5 m/sec)(2) is estimated as 30 days(SRC). 1-Chloro-3-nitrobenzene 's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1-Chloro-3-nitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.097 mm Hg(3) at 25 °C(3).

DRINKING WATER: 1-Chloro-3-nitrobenzene was detected in drinking water in the United States at an unknown location and concentration(1). 1-Chloro-3-nitrobenzene was detected in August 1974 at unknown concentrations in drinking water supplies from three New Orleans finished drinking waters(2). 1-Chloro-3-nitrobenzene was detected at unknown concentrations in drinking water supplies in both Cincinnati, OH and New Orleans, LA on January 1980 and January 1976, respectively(3).|SURFACE WATER: 1-Chloro-3-nitrobenzene was measured at three locations in the Elbe River with concentrations ranging from 0.02 to 0.2 ug/L(1). 1-Chloro-3-nitrobenzene was detected at five locations in the Bormida River (in Italy) at concentrations ranging from 0.002 to 0.19 ug/L(2). 180 ng/L of 1-chloro-3-nitrobenzene in Rhine River water was measured and was believed to be the source of concentrations of 1-chloro-3-nitrobenzene at 4.1 ng/L found during the same time frame in the North Sea(3). Concentrations of 1-chloro-3-nitrobenzene at 3.0 ug/L were measured in Rhine River water.

Occupational exposure may occur through inhalation and dermal contact with this compound at workplaces where 1-chloro-3-nitrobenzene or other nitrobenzene isomers are produced or used. (SRC)

Drug Information

...The metabolism of the three isomers of chloronitrobenzenes /was examined/ in rabbits. Doe rabbits were given [route unspecified] 0.1 g/kg [whether diet or body weight not specified] 2-chloronitrobenzene and 0.2 g/kg 3- and 4-chloronitrobenzenes. Urine was collected over 24-hr periods until metabolites were no longer excreted (usually after 48 hr). The main metabolic processes were reduction and hydroxylation. For each isomer, nearly the entire dose was excreted in urine as the chloroaniline or derivatives of phenolic metabolites. For all three isomers, about 10% of the administered dose was excreted as chloroaniline. The phenols formed were excreted mainly as conjugates with sulfuric and glucuronic acids (66% of the administered dose for 2-chloronitrobenzene, 51% for 3-chloronitrobenzene and 40% for 4-chloronitrobenzene).|Yields m-chloroaniline and 2-chloro-4-nitrophenol in rabbit.|The metabolism of radiolabeled monochloronitrobenzene isomers was compared in isolated hepatocytes and hepatic subcellular fractions from male Fischer-344 rats. ... The major metabolite formed from 3-chloronitrobenzene by isolated hepatocytes was 3-chloroaniline (31% of the added substrate in 90 min). Smaller amounts of 3-chloroaniline-N-glucuronide and 3-chloroacetanilide were formed (7 and 17% of the added 3-chloronitrobenzene, respectively, in 90 min). ... Studies with hepatic microsomes showed that reduction of the chloronitrobenzenes to chloroanilines was inhibited by SKF 525-A, metyrapone, and carbon monoxide, suggesting that cytochrome P-450 played a role in the reaction.|Metabolism of 3-chloronitro[14C]benzene by isolated male Fischer 344 rat hepatocytes produced 3-chloroaniline as the major metabolite (30.9% of total radioactivity). Much smaller quantities of 3-chloroacetanilide (16.7%) and 3-chloroaniline-N-glucuronide (6.7%) were also produced by this isomer.

SYMPTOMS: Symptoms of exposure to this compound may include cyanosis from methemoglobinemia; and blood changes. ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes. (NTP, 1992)

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. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. IMMEDIATELY call a hospital or poison control center even if no symptoms (such as redness or irritation) develop. IMMEDIATELY transport the victim to a hospital for treatment after washing the affected areas. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. IMMEDIATELY call a physician and be prepared to transport the victim to a hospital even if no symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Generally, the induction of vomiting is NOT recommended outside of a physician's care due to the risk of aspirating the chemical into the victim's lungs. However, if the victim is conscious and not convulsing and if medical help is not readily available, consider the risk of inducing vomiting because of the high toxicity of the chemical ingested. Ipecac syrup or salt water may be used in such an emergency. IMMEDIATELY transport the victim to a hospital. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. OTHER: Since this chemical is a known or suspected carcinogen you should contact a physician for advice regarding the possible long term health effects and potential recommendation for medical monitoring. Recommendations from the physician will depend upon the specific compound, its chemical, physical and toxicity properties, the exposure level, length of exposure, and the route of exposure. (NTP, 1992)


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).

/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Consider drug therapy for pulmonary edema ... . Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias if necessary ... Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... .Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/|/SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for shock and treat if necessary ... . Anticipate seizures and treat as necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Nitrates, nitrites, and related compounds/|/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or is in severe respiratory distress. Monitor cardiac rhythm and treat arrhythmias if necessary. Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. If unresponsive to these measures, vasopressors may be helpful. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Administer 1% solution methylene blue if patient is symptomatic with severe hypoxia, cyanosis, and cardiac compromise not responding to oxygen. ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Nitrates, nitrites, and related compounds/

/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.

1-chloro-2-nitrobenzene

The substance can be absorbed into the body by inhalation, through the skin and by ingestion.

Blue lips, fingernails and skin. Dizziness. Headache. Nausea. Confusion. Convulsions.


MAY BE ABSORBED! See Inhalation.


Redness.

1-Chloro-3-nitrobenzene Use and Manufacturing

Methods of Manufacturing

CHLORINATION OF NITROBENZENE IN THE PRESENCE OF FERRIC CHLORIDE|By chlorinating nitrobenzene in the presence of iodine and recrystallizing.|Nitrobenzene is chlorinated at 35 - 45 °C in the presence of sublimed iron(III) chloride to give an isomer mixture containing 86% of the desired 3-isomer. ... Purification is achieved by a combination of distillation and crystallization.

Uses

Intermediate for dyes.

Production

(1972) PROBABLY GREATER THAN 4.54X10+5 GRAMS|(1975) PROBABLY GREATER THAN 4.54X10+5 GRAMS|Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#3096]|This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

ESSENTIALLY 100% AS CHEM INT FOR META-CHLOROANILINE

Benzene, 1-chloro-3-nitro-: ACTIVE

A GAS CHROMATOGRAPHY METHOD FOR THE DETERMINATION OF O-, M-, AND P-NITROCHLOROBENZENE SIMULTANEOUSLY IN AIR IS DESCRIBED. THE SENSITIVITY IS 1 MG/CU M.|Electron capture gas chromatography was used for determination of chlorinated nitrobenzene residues after extraction and cleanup using a procedure based on the Association of Official Analytical Chemists (AOAC) multiresidue method for organochlorine and organophosphorous pesticides in nonfatty foods. Identity of residues was confirmed by GC/mass spectrometry. GC retention times for 15 congeners were determined with OV-101 and mixed OV-210 columns at 130 °C. Recoveries of 15 chlorinated nitrobenzenes from spiked fish samples ranged from 68%-116%. GC of cleaned up fish extract aliquots equivalent to 20 mg sample allowed quantitation of individual congeners at levels of 0.025 and 0.005 ppm with (3)H and 63(Ni) EC detectors, respectively.|Analysis of 1-chloro-3-nitro-benzene in environmental samples employed fused silica capillary column chromatography and mass spectroscopy.|Method: EPA-EAD 1625; Procedure: gas chromatography/mass spectrometry; Analyte: 1-chloro-3-nitrobenzene; Matrix: water; Detection Limit: not provided.|Method: EPA-OSW 8091; Procedure: gas chromatography with electron capture detector or nitrogen-phosphorous detector; Analyte: 1-chloro-3-nitrobenzene; Matrix: water, soil, and waste matrices; Detection Limit: not provided.

Computed Properties

Molecular Weight:157.55
XLogP3:2.5
Hydrogen Bond Acceptor Count:2
Exact Mass:156.9930561
Monoisotopic Mass:156.9930561
Topological Polar Surface Area:45.8
Heavy Atom Count:10
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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