2,3-Dichloronitrobenzene
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2,3-Dichloronitrobenzene
structure -
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CAS No:
3209-22-1
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Formula:
C6H3Cl2NO2
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Chemical Name:
2,3-Dichloronitrobenzene
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Synonyms:
Benzene,1,2-dichloro-3-nitro-;1,2-Dichloro-3-nitrobenzene;2,3-Dichloro-1-nitrobenzene;2,3-Dichloronitrobenzene;NSC 60641
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CAS No:
Description
light yellow to light brown crystalline powder
2,3-dichloronitrobenzene appears as light yellow crystals or yellow crystalline solid. (NTP, 1992)|COLOURLESS-TO-YELLOW CRYSTALS.
2,3-dichloronitrobenzene appears as light yellow crystals or yellow crystalline solid. (NTP, 1992)
2,3-Dichloronitrobenzene Basic Attributes
192
192.00
2048029
221-717-7
985EWS35KG
0251
60641
3077|1578
DTXSID8024997
Monoclinic needles from petroleum ether, acetic acid|Crystallizes as yellow monoclinic needles.
29049085
Characteristics
45.8
3.05
2,3-dichloronitrobenzene appears as light yellow crystals or yellow crystalline solid. (NTP, 1992)
1.721 g/cm3 @ Temp: 14 °C
61.5 °C
257.5 °C
255 °F
1.596
H2O: 67 mg/L
Store below +30°C.
Vapour pressure at 20°C: negligible
Relative vapour density (air = 1): 6.6
Open flame flammable combustion releases toxic nitrogen oxides and chloride fumes
Henry's Law constant = 1.17X10-5 atm-cu m/mol at 25 °C (est)
Hydroxyl radical reaction rate constant = 5.00X10-14 cu cm/molec-sec at 25 °C (est)
Insoluble in water.
Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Can react vigorously with oxidizing materials. (NTP, 1992)
Safety Information
III
9
UN 3077 9/PG 3
3
22-51/53-20/22
60-61-37
CZ5240000
Xn,N
Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives
Stable under normal temperatures and pressures.
P301 + P310
H301
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.|The following wastewater treatment technologies have been investigated for nitrobenzene: Activated carbon and stripping. /Nitrobenzene/|Spillage Disposal: Sweep spilled substance into sealable containers; if appropriate, moisten first to prevent dusting. Carefully collect remainder, then remove to safe place. Do NOT let this chemical enter the environment (extra personal protection: P3 filter respirator for toxic particles).
Organisation for Economic Cooperation and Development; Screening Information Data Set for 2,3-dichloronitrobenzene, CAS # 3209-22-1 (1994). Available from the Database Query page at: http://www.chem.unep.ch/irptc/sids/OECDSIDS/sidspub.html as of June 26, 2007.
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.
|Danger|H301 (83.33%): Toxic if swallowed [Danger Acute toxicity, oral]|P260, P264, P270, P273, P301+P310, P301+P312, P314, P321, P330, P391, P405, and P501|Aggregated GHS information provided by 48 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P260, P264, P270, P280, P301+P312, P302+P352, P307+P311, P314, P321, P330, P332+P313, P362, P405, and P501
Fires involving this compound should be controlled using a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)|Use foam, dry powder, carbon dioxide.
Excerpt from ERG Guide 171 [Substances (Low to Moderate Hazard)]: 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 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. STORAGE PRECAUTIONS: You should store this material in a refrigerator. STORE AWAY FROM SOURCES OF IGNITION. (NTP, 1992)
RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)|Skin: Protective gloves|Inhalation: Local exhaust or breathing protection.
Eyes: Safety spectacles, or eye protection in combination with breathing protection.
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. Carefully collect remainder. Then store and dispose of according to local regulations. Do NOT let this chemical enter the environment.
Separated from bases, strong oxidants and food and feedstuffs.
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.
NO open flames. Prevent deposition of dust. Closed system, dust explosion-proof electrical equipment and lighting.
PREVENT DISPERSION OF DUST!
Use ventilation (not if powder).
Protective gloves.
Wear safety spectacles.
In an analysis of over 4000 industrial wastewater samples from 46 industrial categories, 2,3-dichloronitrobenzene was detected in only one sample (the sample was collected from the organic chemicals industry)(1); concn of the sample and origin of the sample were not reported(SRC).
Toxicity
LD50 SD Rat male oral 381 mg/kg|LD50 SD Rat female oral 512 mg/kg
GENETIC TOXICOLOGY: IN VITRO CYTOGENETICS: Positive in Chromosome Aberrations assay and in Sister Chromatid exchanges. DROSOPHILA (SEX-LINKED RECESSIVE LETHAL/RECIPROCAL TRANSLOCATION): negative. SALMONELLA: weakly positive.
2,3-Dichloronitrobenzene's former production and use as a chemical intermdiate(1) and production as a byproduct of the nitration of 1,2-dichlorobenzene(2) may result in its release to the environment through various waste streams(SRC).
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1,100(SRC), determined from a log Kow of 3.05(2) and a regression-derived equation(3), indicates that 2,3-dichloronitrobenzene is expected to have low mobility in soil(SRC). Volatilization of 2,3-dichloronitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), using a fragment constant estimation method(4). 2,3-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.0X10-3 mm Hg(SRC), determined from a fragment constant method(5). Biodegradation half-lives in excess of 4 weeks using activated sludge(6) suggest 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 1,100(SRC), determined from a log Kow of 3.05(2) and a regression-derived equation(3), indicates that 2,3-dichloronitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 1.2X10-5 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 42 hours and 17 days, respectively(SRC). According to a classification scheme(5), a BCF range of 82-151(6,7) suggests bioconcentration in aquatic organisms is moderate to high(SRC). Biodegradation half-lives in excess of 4 weeks using activated sludge(8) suggest 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), 2,3-dichloronitrobenzene, which has an estimated vapor pressure of 5.9X10-3 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 2,3-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 320 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). 2,3-Dichloronitrobenzene absorbs light at wavelengths of 310 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).
The rate constant for the vapor-phase reaction of 2,3-dichloronitrobenzene with photochemically-produced hydroxyl radicals has been estimated as 5.0X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 321 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,3-Dichloronitrobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,3-Dichloronitrobenzene absorbs light at wavelengths of 310 nm(3) and therefore may be susceptible to direct photolysis by sunlight(SRC).
144.54|A 2,3-dichloronitrobenzene BCF of 82 was determined for guppies (Poecilia reticulata) during 3 day exposure experiments(1). Rainbow trout, under continuous flow conditions and a water concentration of 770 ng/L, had a BCF value of 151 after 36 days exposure(2). According to a classification scheme(3), BCF values of 30 to 100 are moderate and 100 to 1000 are high.
The Koc of 2,3-dichloronitrobenzene is estimated as 1,100(SRC), using a log Kow of 3,05(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,3-dichloronitrobenzene is expected to have low mobility in soil.
The Henry's Law constant for 2,3-dichloronitrobenzene is estimated as 1.2X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,3-dichloronitrobenzene 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 42 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 17 days(SRC). 2,3-Dichloronitrobenzene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 2,3-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.0510-3 mm Hg(SRC), determined from a fragment constant method(3).
DRINKING WATER: 2,3-Dichloronitrobenzene has been qualitatively detected in drinking water concentrates collected from Cincinnati, OH on Oct 17, 1978(1).
Occupational exposure may be through inhalation and dermal contact with 2,3-dichloronitrobenzene as a byproduct at workplaces where 1,2-dichloroobenzene is produced. (SRC)
Drug Information
/Rabbits/ were dosed orally with 2,3-dichloronitrobenzene (0.1 g/kg) and their urine and feces were collected for 72 hr. About 5% of the dose was recovered in feces /and/ ... about 84% of the dose was recovered in urine ... .
2,3-Dichloronitrobenzene undergoes extensive biotransformation in the rabbit. The animals were dosed orally with 2,3-dichloronitrobenzene (0.1 g/kg) and their urine and feces were collected for 72 hr. About 5% of the dose was recovered in feces as 2,3-dichloronitrobenzene and dichloroaniline. About 84% of the dose was recovered in urine, in the form of amino and nitrodichlorophenols: mercapturic acid (0% of dose), glucuronides (47%), sulfates (17%), dichloroaniline-free (15%), dichloroaniline-conjugated (5%), and chlorazoxybenzene (0%).
3.47 Days
ACUTE/CHRONIC HAZARDS: This compound may cause irritation on contact. (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. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. 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: DO NOT INDUCE VOMITING. 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. Be prepared to transport the victim to a hospital if advised by a physician. 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. (NTP, 1992)
Fresh air, rest.
Rinse and then wash skin with water and soap.
Rinse with plenty of water (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/
The substance can be absorbed into the body by ingestion.
Cough.
Redness.
2,3-Dichloronitrobenzene Use and Manufacturing
PROBABLY BY CHLORINATION OF O-CHLORONITROBENZENE IN THE PRESENCE OF AN ANTIMONY CHLORIDE CATALYST|1,2--Dichloro-3-nitrobenzene is a byproduct of the nitration of 1,2-dichlorobenzene.
RESEARCH CHEMICAL|Intermediate reagents in the chemical industry.|Agricultural chemicals.|Antibacterial and antiprotozoal agents.
< 25,000 lb|(1977) NOT PRODUCED COMMERCIALLY IN USA|(1979) NOT PRODUCED COMMERCIALLY IN USA
Benzene, 1,2-dichloro-3-nitro-: ACTIVE
OSW Method 8091. Nitroaromatics and Cyclic Ketones: Capillary Column Technique. Analysis by capillary GC/ECD.|Method: EPA-OSW 8091; Procedure: gas chromatography with either electron capture detection or nitrogen-phosphorus detection; Analyte: 2,3-dichloronitrobenzene; Matrix: water, soil, and waste matrices; Detection Limit: not provided.|Method: EPA-EAD 1625; Procedure: gas chromatography/mass spectrometry; Analyte: 2,3-dichloronitrobenzene; Matrix: water; Detection Limit: not provided.
Computed Properties
Molecular Weight:192.00
XLogP3:3
Hydrogen Bond Acceptor Count:2
Exact Mass:190.9540837
Monoisotopic Mass:190.9540837
Topological Polar Surface Area:45.8
Heavy Atom Count:11
Complexity:159
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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