1-Chloro-2,4-Dinitrobenzene

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position.

Fresh air, rest. Artificial respiration may be needed. Refer for medical attention.

Wear protective gloves when administering first aid. Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer immediately for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Give one or two glasses of water to drink. Do NOT induce vomiting. Refer for medical attention .

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.

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Personal protection: chemical protection suit including self-contained breathing apparatus. Do NOT let this chemical enter the environment. Vacuum with specialist equipment or carefully sweep into sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

... BECAUSE 1-CHLORO-2,4-DINITROBENZENE IS EXTREMELY ALLERGENIC, IT SHOULD BE ONLY USED IN CLOSED /AIR CONDITIONED/ SYSTEMS THAT AFFORD NO HUMAN CONTACT.

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit 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.

THE CONJUGATION OF 1-CHLORO-2,4-DINITROBENZENE WITH GLUTATHIONE BY ... GLUTATHIONE S-TRANSFERASES A, B, AND C IS INHIBITED TO VARYING DEGREES BY ... SEVERAL STEROID SULFATE CONJUGATES, PARTICULARLY BY ESTRADIOL-3,17-DISULFATE AND ESTRADIOL-3-SULFATE.

SKIN SENSITIVITY OF 1-CHLORO-2,4-DINITROBENZENE; 4-CHLORO-3,5-DINITROPHENYL METHYL SULFONE & N,N-DIPROPYL-4-(METHYLSULFONYL)-2,6-DINITROANILINE IN GUINEA PIGS & THEIR CROSS-REACTIONS WITH OTHER NITROBENZENE DERIVATIVES DETERMINED. 4-CHLORO-3,5-DINITROPHENYL METHYL SULFONE & 1-CHLORO-2,4-DINITROBENZENE CROSS-REACTED WITH DNFB.

EC50; Species: Chlorella pyrenoidosa (Green Algae) Exponential Growth Phase, 2 X10+8 cells/L; Conditions: freshwater, static, 25 °C, pH 6.6; Concentration: 800 ug/L for 96 hr (95% confidence interval: 400-1500 ug/L); Effect: growth, general />99% purity formulation/

EC50; Species: Daphnia magna (Water Flea) adult; Conditions: freshwater, static, 19.0-20.0 °C, pH 7.0-7.6, hardness 250 mg/L CaCO3; Concentration: 660 ug/L for 24 hr (95% confidence interval: 640-670 ug/L); Effect: intoxication, immobilization /formulation/

EC50; Species: Daphnia magna (Water Flea) adult; Conditions: freshwater, static, 19.0-20.0 °C, pH 7.0-7.6, hardness 250 mg/L CaCO3; Concentration: 490 ug/L for 48 hr (95% confidence interval: 480-510 ug/L); Effect: intoxication, immobilization /formulation/

LC50; Species: Daphnia magna (Water Flea) age <24 hr; Conditions: freshwater, static, 20 °C, pH 8.2, hardness 250 mg/L CaCO3, dissolved oxygen >6.5 mg/L; Concentration: 800 ug/L for 48 hr (95% confidence interval: 600-1800 ug/L) />99% purity formulation/

For more Ecotoxicity Values (Complete) data for 1-CHLORO-2,4-DINITROBENZENE (8 total), please visit the HSDB record page.

TERRESTRIAL FATE: Based on a classification scheme(1), a measured Koc of 501 in a river sediment(2) and an estimated Koc value of 575(SRC), determined from a structure estimation method(3), indicates that 1-chloro-2,4-dinitrobenzene is expected to have low mobility in soil(SRC). Adsorption to clay can decrease mobility(4). Volatilization of 1-chloro-2,4-dinitrobenzene from moist soil surfaces is expected to occur slowly(SRC) given an estimated Henry's Law constant of 2.45X10-6 atm-cu m/mole(SRC), calculated from its vapor pressure of 8.5X10-5 mm Hg(5) and water solubility of 9.24 mg/L(6). 1-Chloro-2,4-dinitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure. A 0% of theoretical BOD using activated sludge in the Japanese MITI test(7) suggests that biodegradation is slow in the absence of acclimation(SRC). Biodegradation data on structurally similar dinitrobenzenes(8,9) suggest that 1-chloro-2,4-dinitrobenzene will be biodegraded slowly in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), a measured Koc of 501 in a river sediment(2) and an estimated Koc value of 575(SRC), determined from a structure estimation method(3), indicates that 1-chloro-2,4-dinitrobenzene is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(4) based upon an estimated Henry's Law constant of 2.45X10-6 atm-cu m/mole(SRC), calculated from its vapor pressure of 8.5X10-5 mm Hg(5) and water solubility of 9.24 mg/L at 25 °C(6). Using this Henry's Law constant and an estimation method(4), volatilization half-lives for a model river and model lake are 21 and 160 days, respectively(SRC). According to a classification scheme(7), a BCF range of <4.2 to <44 measured in carp(8) suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(8) suggests that biodegradation is slow in the absence of acclimation(SRC). Biodegradation data on structurally similar dinitrobenzenes(9,10) suggest that 1-chloro-2,4-dinitrobenzene will be biodegraded slowly in water(SRC). Photodegradation is expected to occur in surface water exposed to sunlight(SRC) since 1-chloro-2,4-dinitrobenzene absorbs light strongly above 290 nm(11,12); an average photolysis half-life of 32 hours in surface water exposed to sunlight has been reported for this class of compounds(12). Hydrolysis is not expected to be an important fate process for 1-chloro-2,4-dinitrobenzene since this compound lacks functional groups that undergo hydrolysis under environmental conditions(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 1-chloro-2,4-dinitrobenzene, which has a vapor pressure of 8.5X10-5 mm Hg at 25 °C(2), is expected to exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 1-chloro-2,4-dinitrobenzene 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 750 days(SRC), calculated from its rate constant of 2.14X10-14 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3). Particulate-phase 1-chloro-2,4-dinitrobenzene may be removed from the air by wet or dry deposition(SRC). 1-Chloro-2,4-dinitrobenzene absorbs light strongly above 290 nm(4) which suggests that 1-chloro-2,4-dinitrobenzene is susceptible to direct photolysis in the environment(SRC).

/AQUATIC SPECIES/ This study evaluated the activity and expression of the glutathione S-transferase (GST) detoxification isoenzymes in juvenile white sturgeon (Acipenser transmontanus) and Chinook salmon (Oncorhynchus tshawytscha) during acclimation from freshwater (2 per thousand) to estuarine (15 per thousand) salinity conditions. In white sturgeon, GST activity toward 1-chloro-2,4-dinitrobenzene (CDNB) increased significantly (P = 0.005; n = 5) with elevated salinity, but not for the Chinook salmon (P = 0.174; n = 10). ... In conclusion, overall GST activity in white sturgeon, but not Chinook salmon, is stimulated by elevated water salinity, thus electrophilic chemicals such as pesticides may be more effectively detoxified by sturgeon as they undergo seaward migration.

/AQUATIC SPECIES/ Disturbances in antioxidant defenses decrease cellular protection against oxidative stress and jeopardize cellular homeostasis. To knock down the antioxidant defenses of Pacific oyster Crassostrea gigas, animals were pre-treated with 1-chloro-2,4-dinitrobenzene (CDNB) and further challenged with pro-oxidant menadione (MEN). CDNB pre-treatment (10uM for 18 hr) was able to consume cellular thiols in gills, decreasing GSH (53%) and decrease protein thiols (25%). CDNB pre-treatment also disrupted glutathione reductase and thioredoxin reductase activity in the gills, but likewise strongly induced glutathione S-transferase activity (270% increase). Surprisingly, hemocyte viability was greatly affected 24 hr after CDNB removal, indicating a possible vulnerability of the oyster immune system to electrophilic attack. New in vivo approaches were established, allowing the identification of higher rates of GSH-CDNB conjugate export to the seawater and enabling the measurement of the organic peroxide consumption rate. CDNB-induced impairment in antioxidant defenses decreased the peroxide removal rate from seawater. After showing that CDNB decreased gill antioxidant defenses and increased DNA damage in hemocytes, oysters were further challenged with 1 mM MEN over 24 hr. MEN treatment did not affect thiol homeostasis in gills, while CDNB pre-treated animals recovered GSH and PSH to the control level after 24 hr of depuration. Interestingly, MEN intensified GSH and PSH loss and mortality in CDNB-pre-treated animals, showing a clear synergistic effect. The superoxide-generating one-electron reduction of MEN was predominant in gills and may have contributed to MEN toxicity. These results support the idea that antioxidant-depleted animals are more susceptible to oxidative attack, which can compromise survival. Data also corroborate the idea that gills are an important detoxifying organ, able to dispose of organic peroxides, induce phase II enzymes, and efficiently export GSH-CDNB conjugates.

Blue lips, fingernails and skin. Dizziness. Headache. Laboured breathing. Nausea. Vomiting. Blurred vision.

MAY BE ABSORBED! Redness. Pain. Further see Inhalation.

Redness. Pain.

Abdominal pain. Further see Inhalation.

A Koc of 501 was measured for 1-chloro-2,4-dinitrobenzene using a sediment (1.28% organic carbon content) collected from the Yangtse River in China(1). Sorption to montmorillonite clay is stronger (Koc of 6000)(2). Using a structure estimation method based on molecular connectivity indices(3), the Koc of 1-chloro-2,4-dinitrobenzene can be estimated to be 575(SRC). According to a classification scheme(4), Koc values of 501-575 suggests that 1-chloro-2,4-dinitrobenzene is expected to have low mobility in soil. It has been shown that nitrobenzenes adsorb strongly to clay surfaces and the mobility of 1-chloro-2,4-dinitrobenzene is expected to be low in soils rich in clay content(5,6).

/HUMAN EXPOSURE STUDIES/ Contact sensitization by ingredients in personal products is an important clinical problem. It is not clear how sensitization is induced by the generally low concentrations at which they occur but it might be the result of repeated exposure. To compare the strength of contact sensitization induced by a single exposure to 2,4-dinitrochlorobenzene (60 ug cm(-2)) or three repeated exposures to a subsensitizing dose (10 ug cm(-2)). Two groups (n = 10) of healthy adult volunteers were randomized to receive either a single patch of 2,4-dinitrochlorobenzene 60 ug cm(-2) or three once-weekly applications to the same site of 10 ug cm(-2) 2,4-dinitrochlorobenzene. Four weeks after the last application, sensitization was quantified by measurement of responses (skinfold thickness) to a graded series of four challenge doses. All the volunteers were sensitized and the strength of the responses was virtually identical between the groups. The same degree of sensitization was induced by three exposures to 2,4-dinitrochlorobenzene 10 ug cm(-2) as by one exposure to 60 ug cm(-2) of 2,4-dinitrochlorobenzene. Thus repeated exposure to low doses of contact sensitizers may increase the sensitizing potency.

/SIGNS AND SYMPTOMS/ ... Chronic poisoning ... cause gradual onset of symptoms of retrobulbar neuritis, with blurring of vision, central scotoma, esp for green, and constriction of visual fields ... optic neuritis may gradually become evident, in exceptional instances leading to optic atrophy ... pupillary reaction in accommodation /is impaired/ ... .

/SIGNS AND SYMPTOMS/ Typically the retrobulbar neuritis /resulting from chronic poisoning/ has been assoc with peripheral neuritis manifest as paresthesias and pains in the legs and burning of the feet.

/SIGNS AND SYMPTOMS/ Dermal exposure can result in contact urticaria and yellow discoloration of the skin, as well as violent dermatitis.

For more Human Toxicity Excerpts (Complete) data for 1-CHLORO-2,4-DINITROBENZENE (7 total), please visit the HSDB record page.

1-Chloro-2,4-dinitrobenzene's production and use in the manufacture of intermediates for dyes and pesticides(1) and as a reagent for the determination of nicotinic acid, nicotinamide, and other pyridines(2) may result in its release to the environment through various waste streams(SRC).

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, exposure, and use to EPA as cited in the preamble in 51 FR 41329. Effective date: 9-29-06; Reporting date: 11-28-06.

Pursuant to section 8(d) of TSCA, EPA promulgated a model Health and Safety Data Reporting Rule. The section 8(d) model rule requires manufacturers, importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. 1-Chloro-2,4-dinitrobenzene is included on this list. Effective date: 9-29-06; Sunset date: 11-28-06.

Used as a reagent for the detection and determination of pyridine compounds; in the manufacture of azo dyes; as an algicide in coolant water; as an immunostimulant in leprosy and some forms of cancer; and in the treatment of alopecia and warts; [HSDB]

For 1-Chloro-2,4-dinitrobenzene (USEPA/OPP Pesticide Code: 055101) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./

As a reagent for the detection and determination of nicotinic acid, nicotinamide and other pyridine compounds.

Used in the manufacture of intermediates for the production of dyes and pesticides

DNCB is used in the manufacture of dyes and explosives, as a reagent, and as an algicide.

For more Uses (Complete) data for 1-CHLORO-2,4-DINITROBENZENE (6 total), please visit the HSDB record page.

Benzene, 1-chloro-2,4-dinitro- is listed as a High Production Volume (HPV) chemical (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).

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5353]

Production volume for non-confidential chemicals reported under the 2006 Inventory Update Rule. Chemical: Benzene, 1-chloro-2,4-dinitro-. Aggregated National Production Volume: < 500,000 lbs.

Chlorination of dinitrobenzene.

Obtained by nitrating o-nitrochlorobenzene.

Dinitration of chlorobenzene in sulfuric acid.

Although chlorobenzene can be dinitrated directly, this results in unnecessary isomer problems. 4-Chloronitrobenzene is usually nitrated with mixed acid (35/65) at 60 °C to give the pure dinitro isomer. However, 2-chloronitrobenzene can be nitrated to produce 1-chloro-2,4-dinitrobenzene, together with ca. 10 wt% of the isomeric 2-chloro-1,3-dinitrobenzene. This may be separated for disposal, but the mixed isomers are preferably used directly if tolerated by the end product (e.g., sulfur dyes).

Benzene, 1-chloro-2,4-dinitro-: ACTIVE

The mixture of 2,4- and 2,6-dinitrochlorobenzenes (of which the 2,4-compound is present in largest amount) can be separated with an alkaline ethanol-water solution.

Industrially, the most important derivatives of 1-chloro-2,4-dinitrobenzene are obtained by nucleophilic reactions in aqueous media at moderate temperature. Ammonia gives 2,4-dinitroaniline, alkali gives 2,4-dinitrophenol, and methanolic sodium hydroxide gives 2,4-dinitroanisole. Refluxing with hydrazine in ethanol yields 2,4-dinitrophenylhydrazine, a reagent used for the characterization of carbonyl compounds. Reaction with ammonium thiocyanate in aqueous medium at 80 °C gives dinitrophenylrhodanate, which was used as an insecticide. Reaction with substituted anilines gives 2,4-dinitrodiphenylamine derivatives that are used as yellow disperse dyes. Reaction with pyridine gives the reactive (2,4-dinitrophenyl)pyridinium chloride, an intermediate in the preparation of pentamethine dyes.