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Home > Encyclopedia > 2,5-Dichloronitrobenzene

2,5-Dichloronitrobenzene

2,5-Dichloronitrobenzene structure

2,5-Dichloronitrobenzene 

structure
  • CAS No:

    89-61-2

  • Formula:

    C6H3Cl2NO2

  • Chemical Name:

    2,5-Dichloronitrobenzene

  • Synonyms:

    Benzene,1,4-dichloro-2-nitro-;Benzene,1,4-dichloro-3-nitro-;1,4-Dichloro-2-nitrobenzene;2,5-Dichloronitrobenzene;Nitro-p-dichlorobenzene;2,5-Dichloro-1-nitrobenzene;1-Nitro-2,5-dichlorobenzene;1,4-Dichloro-3-nitrobenzene;2-Nitro-1,4-dichlorobenzene;NSC 406125;NSC 6294

  • Categories:

    Chemical Reagents  >  Organic Reagents

Description

yellow flakes


YELLOW FLAKES.

2,5-Dichloronitrobenzene Basic Attributes

192

192.00

778109

201-923-3

IY18G50FF4

1618

406125|6294

1578

DTXSID7052602

Plates or prisms from alcohol, plates from ethyl acetate

29049085

Characteristics

45.8

2.93

YELLOW FLAKES.

1.704 g/cm3 @ Temp: 16 °C

56 °C

267 °C

>230 °F

1.596

soluble in water, ethanol, ether, benzene, carbon disulfide. Slightly soluble in carbon tetrachloride.

Store below +30°C.

<0.1 mm Hg ( 25 °C)

6.6 (vs air)

Oral-rat LD50: 1000 mg/kg; Oral-Mouse LD50: 2850 mg/kg

Open flames are flammable; work with oxidants; high heat release liberates nitrogen oxides and chloride gases

2.4-8.5%(V)

pH = 6.9 (80 mg/L water) at 20 °C

1.20e-05 atm-m3/mole|Henry's Law constant = 1.5X10-5 atm-cu m/mol at 25 °C

log Kow = 2.93 at 25 °C (OECD TG 107)|Hydroxyl radical reaction rate constant = 5X10-14 cu cm/molecule-sec at 25 °C (est)

465 °C

Safety Information

III

9

UN 3077 9/PG 3

2

22-36-51/53

26-60

CZ5260000

Xn,N

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

Stable under normal temperatures and pressures.

P273-P305 + P351 + P338

H302-H319-H411

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal and plant life; and conformance with environmental and public health regulations.

Combustible. Gives off irritating or toxic fumes (or gases) in a fire.

|Warning|H302 (62.5%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P273, P280, P301+P312, P305+P351+P338, P330, P337+P313, P391, and P501|Aggregated GHS information provided by 89 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|Danger|H302: Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P260, P261, P264, P270, P271, P281, P301+P312, P304+P340, P307+P311, P308+P313, P312, P314, P321, P330, P403+P233, P405, and P501|P201, P202, P260, P261, P264, P270, P271, P272, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P312, P314, P321, P330, P332+P313, P333+P313, P337+P313, P363, P403+P233, P405, and P501

Use water spray, dry powder, foam, carbon dioxide.

Explosive limits , vol% in air: 2.4-8.5

SRP: The scientific literature for the use of contact lenses by industrial workers is inconsistent. The benefits or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

A skin and eye irritant.|1,4-Dichloro-2-nitrobenzene is mildly irritating to eyes and non-irritating to skin.

Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. 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 bases, strong oxidants and food and feedstuffs. Store in an area without drain or sewer access. Provision to contain effluent from fire extinguishing.

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

NO open flames.

PREVENT DISPERSION OF DUST!

Use ventilation (not if powder), local exhaust or breathing protection.

Protective gloves.

Wear safety spectacles.

Toxicity

moderately toxic

LD50 Mouse oral 2850 mg/kg|LD50 Rat oral 1210 mg/kg|LD50 Rat dermal > 2,000 mg/kg

/AQUATIC SPECIES/ Following the exposure of algae (Chlorella pyrenoidosa) for 96 hours to 2.1 mg/L, 50% inhibition of growth has been observed... For water fleas (Daphnia magna), 48-hr EC50 value (immobilization) amounts to 11 mg/L and the 21-day EC50 value to 3.8 mg/L. In a semi-static 21-day reproduction test the lowest concentrations at which the population growth rate and mean length of the animals significantly (p<0.01) decreased were 1.8 mg/L and 3.2 mg/L respectively. For fish (Leuciscus idus), the value of acute toxicity (96-hr LC50) in an open system under semi-static conditions is 6.3 mg/L and the corresponding value (48-hr LC50) in a closed system under static conditions is 4.5 mg/L. The lowest 96-hr LC0 was 3.15 mg/L. In the prolonged fish toxicity test under semi-static conditions a 14 day LC50 value of 4.9 mg/L has been found for Poecilia reticulata.|/PLANTS/ 1,4-Dichloro-2-nitrobenzene at concentrations > 42.2 mg/L is phytotoxic (6-day EC50; reduction in fresh weight) to higher plants (seedlings of cucumber and bean).

1,4-Dichloro-2-nitrobenzene's production and use in the manufacture of dyestuff intermediates, pesticides and UV absorbents(1,2) may result in its release to the environment through various waste streams(SRC).

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 590(SRC), determined from a structure estimation method(2), indicates that 1,4-dichloro-2-nitrobenzene is expected to have low mobility in soil(SRC). Volatilization of 1,4-dichloro-2-nitrobenzene from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 1.5X10-5 atm-cu m/mole(3). 1,4-Dichloro-2-nitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00383 mm Hg at 25 °C(4). 1,4-Dichloro-2-nitrobenzene absorbs UV light above 290 nm and will photodegrade in sunlight(4). Utilizing the Japanese MITI test, 4% of the theoretical BOD was reached in four weeks(5) indicating that biodegradation is not an important environmental fate process in soil(SRC).|AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 590(SRC), determined from a structure estimation method(2), indicates that 1,4-dichloro-2-nitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 1.5X10-5 atm-cu m/mole at 25 °C(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 4.4 and 36 days, respectively(SRC). According to a classification scheme(5), observed BCF values of 18-118, measured in carp and rainbow trout(6,7), suggests the potential for bioconcentration in aquatic organisms is low to moderate(SRC). 1,4-Dichloro-2-nitrobenzene has an epilson of 0.00126 at 300 nm in aqueous solution(8) which indicates the compound may be susceptible to direct photolysis(SRC); an approximated quantum yield of 0.01 can be used to estimate a half-life of 34 days in a model sunlit body of water with a 500 cm depth(2). In an aqueous hydrolysis test (OECD Test guideline 111), benzene, 1,4-dichloro-2-nitro was stable to abiotic hydroylsis at pHs 4, 7 and 9 at 25 °C(8). Utilizing the Japanese MITI test, 4% of the theoretical BOD was reached in four weeks(6) indicating that biodegradation is not an important environmental fate process in water(SRC).|ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1,4-dichloro-2-nitrobenzene, which has a vapor pressure of 0.00383 mm Hg at 25 °C(2), expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase 1,4-dichloro-2-nitrobenzene is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 320 days(SRC), calculated from its rate constant of 5X10-14 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). 1,4-Dichloro-2-nitrobenzene absorbs UV light above 290 nm and therefore is photodegraded in sunlight(2).

The rate constant for the vapor-phase reaction of 1,4-dichloro-2-nitrobenzene with photochemically-produced hydroxyl radicals has been estimated as 5X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 320 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Using sunlight as the irradiation source, 1,4-dichloro-2-nitrobenzene had an epilson of 0.00126 at 300 nm in aqueous solution(2) which indicates the compound may be susceptible to direct photolysis(SRC); an approximated quantum yield of 0.01 can be used to estimate a half-life of 34 days in a model sunlit body of water with a 500 cm depth(2). In an aqueous hydrolysis test (OECD Test guideline 111), 1,4-dichloro-2-nitrobenzene was stable to abiotic hydroylsis at pHs 4, 7 and 9 at 25 °C(2).

112.20|BCF values of 18-103 were measured for 1,4-dichloro-2-nitrobenzene in carp (Cyprinus carpio) at concentrations of 5-50 ug/L over a 6-week exposure period(1). A mean 1,4-dichloro-2-nitrobenzene BCF of 118 was measured in rainbow trout over a 36-day exposure period(2). According to a classification scheme(3), these BCF values suggest the potential for bioconcentration in aquatic organisms is low to moderate(SRC). In a static container 3-day exposure test, a BCF of 1047 was measured in guppies (Poecilla reticulata)on a fat-weight basis(4).

Using a structure estimation method based on molecular connectivity indices(1), the Koc of 1,4-dichloro-2-nitrobenzene can be estimated to be 590(SRC). According to a classification scheme(2), this estimated Koc value suggests that 1,4-dichloro-2-nitrobenzene is expected to have low mobility in soil. 1,4-Dichloro-2-nitrobenzene did not leach in column leachate tests designed to assess leaching potential from wastes in landfill sites(3).

The Henry's Law constant for 1,4-dichloro-2-nitrobenzene is 1.5X10-5 atm-cu m/mole(1). This Henry's Law constant indicates that 1,4-dichloro-2-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 4.4 days 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 36 days(SRC). 1,4-Dichloro-2-nitrobenzene's Henry's Law constant indicates that volatilization from moist soil surfaces may occur(SRC). 1,4-Dichloro-2-nitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 0.00383 mm Hg at 25 °C(3).

SURFACE WATER: 1,4-Dichloro-2-nitrobenzene was not detected (detection limit of 0.07 ng/L) in water samples collected from open waters of the North Sea in July 1993(1). 1,4-Dichloro-2-nitrobenzene was not detected (detection limit of 10 ng/L) in water samples collected from the Elbe River in Germany in 1992/1993(2).

Occupational exposure to 1,4-dichloro-2-nitrobenzene may occur through dermal contact with this compound at workplaces where 1,4-dichloro-2-nitrobenzene is produced or used(SRC). 1,4-Dichloro-2-nitrobenzene is not contained in consumer products(1); therefore, exposure to the general population will not occur via contact with consumer products(SRC).

Drug Information

1,4-Dichloro-2-nitrobenzene is readily absorbed after oral administration or dermal application.

1,4-Dichloro-2-nitrobenzene is readily absorbed after oral administration or dermal application. The substance is metabolized to a number of products. Following oral application chiefly 2,5-dichloroaniline, the mercapturic acid derivative N-acetyl-S-(4-chloro-2-nitrophenyl)-L-cysteine as well as glucuronic and sulfuric acid conjugates of 4-amino-2,5-dichlorophenol were identified in urine.

3.63 Days|Following oral intake the biological half-life in fish is less than 3 days.

Fresh air, rest.


Rinse and then wash skin with water and soap.


Rinse with plenty of water (remove contact lenses if easily possible).

/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B/|/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 needed. 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 ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B/|/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. 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 as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's 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 ... . /Poisons A and B/

/OTHER TOXICITY INFORMATION/ 1,4-Dichloro-2-nitrobenzene is mildly irritating to eyes and non-irritating to skin. When tested in animals the product has been proved to be a non-sensitizer; however, there are indications of skin sensitization in man.

2,5-dichloronitrobenzene

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

Redness.

2,5-Dichloronitrobenzene Use and Manufacturing

Methods of Manufacturing

The preparation method is based on p-dichlorobenzene as raw material, adding concentrated nitric acid, concentrated sulfuric acid and a small amount of water for nitrification.

Uses

2,5-Dichloronitrobenzene is a reagent used in the synthesis of antitrypanosomal, antileishmanial and antimalarial agents. Also it is used in the synthesis of lysophosphatidic acid acyltransferase-β inhibitors.

Production

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#7980]

Benzene, 1,4-dichloro-2-nitro-: ACTIVE|TP - indicates a substance that is the subject of a proposed TSCA section 4 test rule.

Method: EPA-RCA 8091 (ECD); Procedure: gas chromatograph with electron capture detector; Analyte: 2,5-dichloronitrobenzene; Matrix: water, soil, and waste matrices; Detection Limit: not provided.|Method: EPA-RCA 8091 (NPD); Procedure: gas chromatograph with nitrogen-phosphorus detection; Analyte: 2,5-dichloronitrobenzene; Matrix: water, soil, and waste matrices; Detection Limit: not provided.

Computed Properties

Molecular Weight:192.00
XLogP3:2.9
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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