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Home > Encyclopedia > 2,4-Dichloronitrobenzene

2,4-Dichloronitrobenzene

2,4-Dichloronitrobenzene structure

2,4-Dichloronitrobenzene 

structure
  • CAS No:

    611-06-3

  • Formula:

    C6H3Cl2NO2

  • Chemical Name:

    2,4-Dichloronitrobenzene

  • Synonyms:

    Benzene,2,4-dichloro-1-nitro-;2,4-Dichloro-1-nitrobenzene;2,4-Dichloronitrobenzene;1,3-Dichloro-4-nitrobenzene;4-Nitro-1,3-dichlorobenzene;NSC 43196

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

yellow crystals


2,4-dichloronitrobenzene appears as light yellow needles or amber crystalline solid. (NTP, 1992)|YELLOW CRYSTALS OR LIQUID.


2,4-dichloronitrobenzene appears as light yellow needles or amber crystalline solid. (NTP, 1992)

2,4-Dichloronitrobenzene Basic Attributes

192

192.00

1451655

210-248-3

85P1A896RR

0252

43196

2811|1578

DTXSID3024998

Crystallizes as pale yellow needles from ethanol.

29049085

Characteristics

45.8

3.1

Yellow-brown Crystalline Low Melting Solid

1.4790 g/cm3 @ Temp: 80 °C

34 °C

258.5 °C

>230 °F

1.5512 (78.1ºC)

H2O: 188 mg/L (20 ºC)

Store below +30°C.

Vapour pressure, Pa at 20°C: 1

Relative vapour density (air = 1): 6.6

LD50 orally in Rabbit: 380 mg/kg LD50 dermal Rat 920 mg/kg

Open flame is flammable; high heat releases nitrogen oxide and chloride gas; works with oxidant

Henry's Law constant = 3.22X10-5 atm-cu m/mol at 25 °C (est)

Hydroxyl radical reaction rate constant = 1.21X10-13 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)

500 °C

Safety Information

III

9

2811

3

36/37/38-51/53-43-21/22

26-36-61-36/37-24

CZ5420000

Xi,N,Xn

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

Stable. Combustible. Incompatible with strong oxidizing agents, strong bases.

P261-P305 + P351 + P338

H315-H319-H335

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/

European Chemicals Bureau; IUCLID Dataset, 1,3-Dichloro-4-nitrobenzene (CAS # 611-06-3) p. 23 (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of July 5, 2007.

This chemical is combustible. (NTP, 1992)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Danger|H302 (28.07%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P322, P330, P332+P313, P333+P313, P337+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 57 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P272, P280, P281, P301+P312, P302+P352, P308+P313, P312, P314, P321, P322, P330, P333+P313, P361, P363, P405, and P501

Fires involving this chemical can be controlled using a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)|Use powder, water spray, foam, carbon dioxide.

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-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 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)

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Sweep spilled substance into sealable containers. If appropriate, moisten first to prevent dusting. Do NOT let this chemical enter the environment.

Separated from bases, strong oxidants and food and feedstuffs. Provision to contain effluent from fire extinguishing.

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 DISPERSION OF DUST!

Use ventilation (not if powder).

Protective gloves.

Wear safety spectacles.

2,4-Dichloronitrobenzene was detected not quantified in sediment from an unidentified river in Japan(1).

Toxicity

Changes were characterized in the dose mutagenic response curve of 99% 2,4-dinitrochlorobenzene (DNCB) modified by adding 1% concn of known contaminants: 1-chloro-2-nitrobenzene, 1,3-dinitrobenzene, and 2,4-dichloronitrobenzene. Dose response curves were generated by using Salmonella typhimurium testers strains in a modified Ames assay. A linear dose response ralationship was observed with a slight, but nonsignificant, shift to the right when contaminants were added.

LD50 Rat oral 379 mg/kg|LD50 Rat oral 990 mg/kg|LD50 Rat dermal 921 mg/kg|LD50 Mouse oral 790 mg/kg|LD50 Rabbit dermal 921 mg/kg

IN VITRO CYTOGENETICS NEGATIVE (CHROMOSOME ABERRATIONS) NEGATIVE (SISTER CHROMATID EXCHANGES); DROSOPHILA (SEX-LINKED RECESSIVE LETHAL/RECIPROCAL TRANSLOCATION) NEGATIVE; SALMONELLA POSITIVE

2,4-Dichloronitrobenzene's production and use as a chemical intermediate(1) and in the production of 2,4-dichloroaniline(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 3.07(2) and a regression-derived equation(3), indicates that 2,4-dichloronitrobenzene is expected to have low mobility in soil(SRC). Volatilization of 2,4-dichloronitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.2X10-6 atm-cu m/mole(4). 2,4-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-2 mm Hg(SRC), determined from a fragment constant method(5). A less than 0.1% biodegradation loss in a 5-day BOD test using activated sludge(6) suggests 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 3.07(2) and a regression-derived equation(3), indicates that 2,4-dichloronitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a estimated Henry's Law constant of 3.2X10-5 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 2 and 17 days, respectively(SRC). According to a classification scheme(5), experimental BCF values of 80 to 120(2,6,7) suggests bioconcentration in aquatic organisms is moderate to high. A less than 0.1% biodegradation loss in a 5-day BOD test using activated sludge(7) suggests 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), 2,4-dichloronitrobenzene, which has an estimated vapor pressure of 1.4X10-2 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 2,4-dichloronitrobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 130 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). 2,4-Dichloronitrobenzene contains chromophores that absorb at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(SRC).

The rate constant for the vapor-phase reaction of 2,4-dichloronitrobenzene with photochemically-produced hydroxyl radicals has been estimated as 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 130 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2,4-Dichloronitrobenzene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). 2,4-Dichloronitrobenzene contains chromophores that absorb at wavelengths >290 nm(2) and therefore may be susceptible to direct photolysis by sunlight(SRC).

117.49|A BCF value of 84 was measured in guppies (Poecilia reticulata) during 3-day exposure to 2,4-dichloronitrobenzene(1). A 3-day exposure BCF of 80 was determined for golden ide fish (Leuciscus idus melanotus)(2). Rainbow trout, under continuous flow conditions and a water concentration of 750 ng/L, had a BCF value of 120 after 36 days exposure(3). According to a classification scheme(4), BCF values of 30 to 100 are moderate and 100 to 1000 are high. A 1-day exposure BCF of 150 was reported for green algae (Chlorella fusca)(2).

The Koc of 2,4-dichloronitrobenzene is estimated as 1,100(SRC), using a log Kow of 3.07(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2,4-dichloronitrobenzene is expected to have low mobility in soil.

The Henry's Law constant for 2,4-dichloronitrobenzene is estimated as 3.2X10-5 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2,4-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 41 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). 2,4-Dichloronitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.4X10-2 mm Hg(SRC), determined from a fragment constant method(3).

DRINKING WATER: 2,4-Dichloronitrobenzene has been qualitatively detected in drinking water concentrates collected from Cincinnati, OH on Oct 17, 1978 and in drinking water concentrates collected from Seattle, WA on Nov 11, 1976(1).

Occupational exposure to 2,4-dichloronitrobenzene may occur through inhalation and dermal contact with this compound at workplaces where 2,4-dichloronitrobenzene is produced or used. (SRC)

Drug Information

The metabolism of 2,3-, 2,4-, 2,5-, 2,6-, 3,4-, and 3,5-dichloro-1-nitrobenzene by Mucor javanicus was investigated, together with 2,4-dichloro-1-nitrobenzene metabolism by other fungi. The main metabolites were the corresponding dichloroanilines, accompanied by a lesser amt of 2,5-dichloro-1-nitrobenzene and 2,6-dichloro-1-nitrobenzene (3-or4-substituted) from 2,3-dichloro-1-nitrobenzene or 2,4-dichloro-1-nitrobenzene, respectively. Similar metabolic patterns were observed with M griseocyanus, M praini, M hiemalis, or Aspergillus flavus.

6.76 Days

Excerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]: TOXIC; inhalation, ingestion or skin contact with material may cause severe injury or death. 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. (ERG, 2016)

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/

2,4-dichloro-1-nitrobenzene

Cough.


Redness.

2,4-Dichloronitrobenzene Use and Manufacturing

Methods of Manufacturing

1,3-Dichlorobenzene is nitrated with mixed acid, and the product is separated from the resulting isomer mixture.

Uses

It is an important intermediate for pesticides, medicines, dyes and other organic chemical products

Benzene, 2,4-dichloro-1-nitro-: ACTIVE|2,4-Dichloronitrobenzene is reduced to the intermediate 2,4-dichloroaniline. Preferential amination in the ortho position can be effected to give 5-chloro-2-nitroaniline ... .

Method: EPA-OSW 8091; Procedure: gas chromatography with either electron capture detection or nitrogen-phosphorus detection; Analyte: 2,4-dichloronitrobenzene; Matrix: water, soil, and waste matrices; Detection Limit: not provided.

Computed Properties

Molecular Weight:192.00
XLogP3:3.1
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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