1-Chloro-2,4-dinitrobenzene
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1-Chloro-2,4-dinitrobenzene
structure -
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CAS No:
97-00-7
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Formula:
C6H3ClN2O4
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Chemical Name:
1-Chloro-2,4-dinitrobenzene
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Synonyms:
Benzene,1-chloro-2,4-dinitro-;1-Chloro-2,4-dinitrobenzene;1,3-Dinitro-4-chlorobenzene;2,4-Dinitrochlorobenzene;2,4-Dinitro-1-chlorobenzene;DNCB;4-Chloro-1,3-dinitrobenzene;Dinitrochlorobenzene;2,4-Dinitrophenyl chloride;CDNB;6-Chloro-1,3-dinitrobenzene;1-Chloro-2,4-nitrobenzene;2-Chloro-1,5-dinitrobenzene;NSC 6292
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CAS No:
Description
yellow crystals with an almond odour
1-chloro-2,4-dinitrobenzene appears as pale yellow needles, almond odor.|PALE YELLOW CRYSTALS WITH CHARACTERISTIC ODOUR.
1-chloro-2,4-dinitrobenzene appears as pale yellow needles, almond odor.|1-chloro-2,4-dinitrobenzene is a C-nitro compound that is chlorobenzene carrying a nitro substituent at each of the 2- and 4-positions. It has a role as an epitope, an allergen and a sensitiser. It is a C-nitro compound and a member of monochlorobenzenes.|Dinitrochlorobenzene has been used in trials studying the treatment of HIV Infections.|Dinitrochlorobenzene is an aromatic hydrocarbon composed of a benzene ring linked to two nitro groups and one chloride with potential use as an indicator for glutathione S-transferase (GST) activity, in the evaluation of T-cell immunocompetence, and as a treatment for warts. The chloride group of dinitrochlorobenzene (DNCB) is susceptible to nucleophilic substitution and is a target for GST-dependent glutathione conjugation in vitro; upon conjugation of the thiol group of glutathione to the DNCB substrate, there is an increase in the absorbance at 340 nm, which permits an indirect quantitation of GST activity in a sample. DNCB induces a type IV hypersensitivity reaction in most patients; therefore, exposure to DNCB can yield an indirect measurement of T-cell activity in a patient and immunocompromised patients may demonstrate decreased hypersensitivity toward DNCB. Following direct application to a wart, DNCB induces an allergic inflammatory response that may cure the viral infection that caused the wart.|A skin irritant that may cause dermatitis of both primary and allergic types. Contact sensitization with DNCB has been used as a measure of cellular immunity. DNCB is also used as a reagent for the detection and determination of pyridine compounds.
1-Chloro-2,4-dinitrobenzene Basic Attributes
202.55
202.55
613161
202-551-4
GE3IBT7BMN
0416
6292
1577|3441
DTXSID6020278
C439
Yellow crystals|Pale yellow needles
2904902000
Characteristics
91.6
2.17 (estimated)
Yellow to brown Crystalline Mass, Chunks or Crystals and Powder
1.7 g/cm3
54 °C
315 °C
367 °F
1.625
H2O: insoluble ;alcohol: very slightly soluble (cold)(lit.)
Store below +30°C.
Vapour pressure at 20°C: negligible
Relative vapour density (air = 1): 7.0
Oral-rat LD50: 780 mg/kg
Combustible; in case of open flame or heated to above 150℃, there is a risk of combustion and explosion; high heat decomposition of toxic nitrogen oxides and chloride fumes
1.9-22%(V)
Almond odor
Henry's Law constant = 2.45X10-6 atm-cu m/mole at 25 °C (est)
Can exist in three forms: one stable and two labile; the stable alpha-form crystallizes in yellow rhombic crystals from diethyl ether; MP alpha-form is 53.4 °C, beta-form 43 °C, and 27 °C|DENSITY OR SP GR : 1.6867 @ 16 °C /BETA FORM/; MELTING POINT: 53 °C /ALPHA FORM, STABLE/|YELLOW RHOMBIC CRYSTALS /ALPHA FORM/|YELLOW RHOMBIC CRYSTALS FROM ETHER, NEEDLES FROM ALCOHOL /BETA FORM/|Hydroxyl radical reaction rate constant = 2.14X10-14 cu cm/molecule-sec at 25 °C (est)
No rapid reaction with air No rapid reaction with water
Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic
Explosive
Self-reactive [Halpern, Chem. and Eng. News, 29:2666(1951)]. The mixture of this ompound with hydrazine hydrate caused a violent reaction.
432 °C
Lower flammable limit: 2% by volume; Upper flammable limit: 22% by volume
Critical temperature: 813.8 deg K; critical pressure: 3.49X10+6 Pa (est)
Safety Information
II
6.1
UN 3441 6.1/PG 2
2
23/24/25-33-50/53-43-41-38
28-36/37-45-60-61-28A-24
CZ0525000
T,N
Treasury is ventilated at low temperature and dry; stored separately from oxidants and food additives
Toxic
Explosive when mixed with air
Stable. Combustible. Incompatible with strong oxidizing agents, ammonia. Reacts violently with hydrazine hydrate.
P261-P273-P280-P301 + P310-P302 + P350-P305 + P351 + P338
H301 + H331-H310-H315-H317-H318-H373-H410
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.
Explosive reaction with ammonia at 170 °C/40 bar.|Reacts violently with hydrazine sulfate or hydrazine hydrate.|In absence of diluent, the reaction is ... violent to shatter the flask.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors and sewers explosion hazards. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. (ERG, 2016)|Combustible. Gives off irritating or toxic fumes (or gases) in a fire. Finely dispersed particles form explosive mixtures in air.|Reactive - 4th degree
|Danger|H301: Toxic if swallowed [Danger Acute toxicity, oral]|P260, P261, P264, P270, P271, P273, P280, P301+P310, P302+P352, P304+P340, P311, P312, P314, P321, P322, P330, P361, P363, P391, P403+P233, P405, and P501|H301+H331 (35.19%): Toxic if swallowed or if inhaled [Danger Acute toxicity, oral; acute toxicity, inhalation]|P260, P261, P262, P264, P270, P271, P272, P273, P280, P301+P310, P301+P312, P302+P350, P302+P352, P304+P340, P305+P351+P338, P310, P311, P312, P314, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P391, P403+P233, P405, and P501|Aggregated GHS information provided by 109 companies from 18 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, P262, P264, P270, P271, P272, P280, P281, P301+P312, P302+P350, P302+P352, P304+P340, P305+P351+P338, P307+P311, P308+P313, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P361, P362, P363, P403+P233, P405, and P501
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: ELIMINATE all ignition sources (no smoking, flares, sparks or flames in immediate area). Do not touch damaged containers or spilled material unless wearing appropriate protective clothing. Stop leak if you can do it without risk. Prevent entry into waterways, sewers, basements or confined areas. Absorb or cover with dry earth, sand or other non-combustible material and transfer to containers. DO NOT GET WATER INSIDE CONTAINERS. (ERG, 2016)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: 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. (ERG, 2016)
Combustible when exposed to heat or flame.
A moderate explosion hazard when exposed to flame, sparks, heated to 150 °C, or when shocked in a sealed container. Explosive reaction with ammonia at 170 °C/40 bar.|It has been used as an explosive.|Explosive limits , vol% in air: 2.0-22
To fight fire use /carbon dioxide/, dry chemical.
... 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.
/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Health: 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. /Chlorodinitrobenzenes; Chlorodinitrobenzenes, liquid; Chlorodinitrobenzenes, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (COMBUSTIBLE)/ Fire or Explosion: Combustible material: may burn but does not ignite readily. When heated, vapors may form explosive mixtures with air: indoors, outdoors, and sewers explosion hazards. Those substances designated with a "P" may polymerize explosively when heated or involved in a fire. Contact with metals may evolve flammable hydrogen gas. Containers may explode when heated. Runoff may pollute waterways. Substance may be transported in a molten form. /Chlorodinitrobenzenes; Chlorodinitrobenzenes, liquid; Chlorodinitrobenzenes, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. Ventilate enclosed areas. /Chlorodinitrobenzenes; Chlorodinitrobenzenes, liquid; Chlorodinitrobenzenes, solid/|/GUIDE 153: SUBSTANCES - TOXIC AND/OR CORROSIVE (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. /Chlorodinitrobenzenes; Chlorodinitrobenzenes, liquid; Chlorodinitrobenzenes, solid/|For more DOT Emergency Guidelines (Complete) data for 1-CHLORO-2,4-DINITROBENZENE (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.
SKIN IRRITANT.|Eye irritant /2,4-Dinitrobenzene/|The cmpd is irritating to the skin of rabbits & highly irritating to their eyes.|A severe human skin & eye irritant.
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.
Fireproof. Separated from strong oxidants, strong bases, strong reducing agents, food and feedstuffs and ammonia. Store in an area without drain or sewer access.
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.
The substance is severely irritating to the skin and eyes. The substance may cause effects on the blood. This may result in the formation of methaemoglobin. Exposure to high concentrations could cause death.
Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the blood. This may result in a decrease in haemoglobin and a decrease of blood cells.
NO open flames. NO contact with incompatible substances. See Chemical Dangers. Do NOT expose to friction or shock.
PREVENT DISPERSION OF DUST! AVOID ALL CONTACT! FIRST AID: USE PERSONAL PROTECTION.
Use local exhaust or breathing protection.
Protective gloves. Protective clothing.
Wear face shield or eye protection in combination with breathing protection.
| 3 - Materials that, under emergency conditions, can cause serious or permanent injury.| 4 - Materials that rapidly or completely vaporize at atmospheric pressure and normal ambient temperature or that are readily dispersed in air and burn readily.| 0 - Materials that in themselves are normally stable, even under fire conditions.
1-Chloro-2,4-dinitrobenzene was identified, not quantified, in water effluent from sulfur dye production(1).
Toxicity
moderately toxic
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.
LD50 Rat ip 280 mg/kg|LD50 Rabbit skin 130 mg/kg|LD50 Rat oral 780 mg/kg
/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.
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).
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).
The rate constant for the vapor-phase reaction of 1-chloro-2,4-dinitrobenzene with photochemically-produced hydroxyl radicals has been estimated as 2.14X10-14 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 750 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 1-Chloro-2,4-dinitrobenzene absorbs UV light strongly above 290 nm(2) which suggests that 1-chloro-2,4-dinitrobenzene is susceptible to direct photolysis in the environment(SRC). In aqueous solution, dinitrobenzenes have quantum yields generally greater than 0.001 at 313 nm(3) indicating that direct photolysis will occur in sunlight(SRC); an average photolysis half-life of 32 hours in surface water exposed to sunlight has been reported for this class of compounds(3). 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).
The BCF in carp (Cyprinus carpio) ranged from <4.2 to <44 at test concentrations of 1-10 ppb 1-chloro-2,4-dinitrobenzene over a 6-week exposure period(1). According to a classification scheme(2), these BCF values suggest the potential for bioconcentration in aquatic organisms is low(SRC).
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).
The Henry's Law constant for 1-chloro-2,4-dinitrobenzene is estimated as 2.45X10-6 atm-cu m/mole(SRC) calculated from its vapor pressure of 8.5X10-5 mm Hg(1) and water solubility of 9.24 mg/L(2). This Henry's Law constant indicates that 1-chloro-2,4-dinitrobenzene is expected to volatilize from water surfaces(3). 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 21 days(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 160 days(SRC). 1-Chloro-2,4-dinitrobenzene's Henry's Law constant indicates that volatilization from moist soil surfaces is expected to occur slowly(SRC). 1-Chloro-2,4-dinitrobenzene is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(1).
SURFACE WATER: 1-Chloro-2,4-dinitrobenzene has been detected in the Rhine river at concentrations of <0.01 ug/L in 1978 and 1979(1). 1-Chloro-2,4-dinitrobenzene concentrations of 0.005 to 0.026 ug/L were detected in water samples collected from 3 sites on Yellow River in China (at 9 other sites, levels were below detection limits)(2).
According to the 2006 TSCA Inventory Update Reporting data, the number of persons reasonably likely to be exposed in the industrial manufacturing, processing, and use of 1-chloro-2,4-dinitrobenzene is 100 to 999; the data may be greatly underestimated(1).|NIOSH (NOES Survey 1981-1983) has statistically estimated that 170 workers (14 of these are female) are potentially exposed to 1-chloro-2,4-dinitrobenzene in the US(1). Occupational exposure to 1-chloro-2,4-dinitrobenzene may occur through dermal contact with this compound at workplaces where 1-chloro-2,4-dinitrobenzene is produced or used(SRC).
Drug Information
2,4-Dinitrochlorobenzene is a potent sensitizer that has been applied topically in the evaluation of delayed hypersensitivity. It has also been used as an immunostimulant in various conditions including some forms of cancer, and in the treatment of alopecia and warts. It has also been investigated in HIV infection and leprosy.
Drugs that act locally on cutaneous or mucosal surfaces to produce inflammation; those that cause redness due to hyperemia are rubefacients; those that raise blisters are vesicants and those that penetrate sebaceous glands and cause abscesses are pustulants; tear gases and mustard gases are also irritants. (See all compounds classified as Irritants.)|Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)
THE CONJUGATION OF DRUGS AND OTHER FOREIGN CMPD /SUCH AS 1-CHLORO-2,4-DINITROBENZENE/ WITH GLUTATHIONE LEADS TO THE FORMATION OF N-ACETYLCYSTEINE (OR MERCAPTURIC ACID) DERIVATIVES.|YIELDS S-(4-CHLORO-3-NITROPHENYL)GLUTATHIONE IN TICKS, LOCUST, HOUSEFLIES, GRASS GRUBS AND PIGEONS /FROM TABLE/|Metabolism studies have demonstrated that 1-chloro-2,4-dinitrobenzene depletes hepatic GSH levels by the biotransformation displacement of chlorine to yield 1-SG-2,4-dinitrobenzene.|1-chloro-2,4-dinitrobenzene has known human metabolites that include 2-amino-5-[[1-(carboxymethylamino)-3-(1-chloro-2,4-dinitrocyclohexa-2,5-dien-1-yl)sulfanyl-1-oxopropan-2-yl]amino]-5-oxopentanoic acid and S-(2,4-dinitrophenyl)glutathione.
The Thioredoxin (Trx)/Thioredoxin reductase (TrxR)-system has emerged as a crucial component of many cellular functions particularly antioxidant defence. We investigated the effect of the selective TrxR inhibitor 1-chloro-2,4-dinitrobenzene (CDNB) on survival and redox status in neuronal cell lines. CDNB was found to cause apoptosis without depletion of glutathione or loss of mitochondrial complex I-activity. Cells treated with CDNB displayed an early increase of reactive oxygen species and rapid activation of stress inducible protein kinases c-Jun N-terminal kinase (JNK) and mitogen activated protein kinase kinase 4 (MKK4). Thus TrxR inhibition by CDNB results in generation of reactive oxygen species and subsequent activation of stress-inducible kinases without impairment of the cellular antioxidant status or mitochondrial function. Inhibition of the specific kinases involved in cell death triggered by Trx/TrxR dysfunction could represent a novel and selective therapeutic approach in neurodegenerative disorders.|Prolonged topical exposure of BALB/c mice to chemical contact and respiratory allergens stimulates, respectively, preferential Th1- and Th2-type responses with respect to serum Ab isotype and cytokine secretion phenotypes displayed by draining lymph node cells. ... Differential cytokine secretion patterns are induced rapidly in the skin following first exposure to the contact allergen 2,4-dinitrochlorobenzene and the respiratory sensitizer trimellitic anhydride. Trimellitic anhydride induced early expression of IL-10, a cytokine implicated in the negative regulation of Langerhans cell (LC) migration, whereas exposure to 2,4-dinitrochlorobenzene resulted in production of the proinflammatory cytokine IL-1beta. Associated with this, trimellitic anhydride provoked LC migration with delayed kinetics compared with 2,4-dinitrochlorobenzene, and local neutralization of IL-10 caused enhanced LC mobilization in response to trimellitic anhydride with concomitant up-regulation of cutaneous IL-1beta. ... These differential epidermal cytokine profiles contribute to the polarization of immune responses to chemical allergens via effects on the phenotype of activated dendritic cells arriving in the draining lymph node. Thus, trimellitic anhydride-exposed dendritic cells that have been conditioned in vivo with IL-10 (a potent inhibitor of the type 1-polarizing cytokine IL-12) are effective APCs for the development of a Th2-type response.|Repeated topical exposure of BALB/c strain mice to chemical contact and respiratory allergens results in preferential T helper (Th)1- and Th2-cell activation, respectively. In addition, it has been shown that respiratory allergens, such as trimellitic anhydride, stimulate epidermal Langerhans cell (LC) migration with delayed kinetics compared with contact allergens, such as 2, 4-dinitrochlorobenzene. Experiments using anti-interleukin (IL)-10 antibodies in vivo suggest that cutaneous IL-10 may contribute to the differential regulation of LC migration by these chemicals. To investigate further the mechanistic basis for the development of polarised immune responses, we have examined the production of epidermal cytokines provoked following a single topical application to BALB/c strain mice of 2, 4-dinitrochlorobenzene (1%), trimellitic anhydride (25%) or vehicle (acetone:olive oil, 4:1; AOO). Skin explants were excised from mice exposed on the dorsum of both ears for various periods (30min-6hr) to chemical and were cultured on medium prior to analysis of supernatants for the presence of tumour necrosis factor alpha (TNF-alpha), IL-1beta, IL-1alpha, IL-6, IL-10, IL-12p40, IL-12p70 and IL-17 using the Bio-PlexTM cytokine array system. Enhanced production of IL-1beta, a cytokine involved in the initiation of LC migration, was detected only following exposure to 2, 4-dinitrochlorobenzene, with 15- fold increases induced by 6hr of exposure. In addition, only exposure to 2, 4-dinitrochlorobenzene was associated with early (2 hr) secretion of IL-17. In contrast, up-regulation of IL- 10, a cytokine that inhibits LC mobilization, was evident only for trimellitic anhydride during the first 3 hr of exposure, with 2 to 3-fold increases in IL-10 release being induced. Small increases in IL-1alpha levels were apparent for both chemicals. No alterations in either IL-6, IL-12p40 or IL-12p70 secretion were recorded and TNF-alpha remained undetectable throughout. These data suggest that discrete epidermal cytokine secretion profiles induced following exposure to chemical contact and respiratory allergens might contribute to the polarization of immune responses, possibly through effects on LC function.
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (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)
Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: Ensure that medical personnel are aware of the material(s) involved and take precautions to protect themselves. Move victim to fresh air. Call 911 or emergency medical service. Give artificial respiration if victim is not breathing. Do not use mouth-to-mouth method if victim ingested or inhaled the substance; give artificial respiration with the aid of a pocket mask equipped with a one-way valve or other proper respiratory medical device. Administer oxygen if breathing is difficult. Remove and isolate contaminated clothing and shoes. In case of contact with substance, immediately flush skin or eyes with running water for at least 20 minutes. For minor skin contact, avoid spreading material on unaffected skin. Keep victim calm and warm. Effects of exposure (inhalation, ingestion or skin contact) to substance may be delayed. (ERG, 2016)
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.
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 as necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on 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. /Nitrates, nitrites, and related compounds/|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/|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/
/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.
Chlorodinitrobenzene
The substance can be absorbed into the body through the skin and by ingestion.
Blue lips, fingernails and skin. Dizziness. Headache. Laboured breathing. Nausea. Vomiting. Blurred vision.
MAY BE ABSORBED! Redness. Pain. Further see Inhalation.
Redness. Pain.
1-Chloro-2,4-dinitrobenzene Use and Manufacturing
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).
1-Chloro-2,4-dinitrobenzene is a benzene derivative and is used in biochemical research as a substrate for glutathione S-transferase.
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#5358]|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.
Grades: technical, fused
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.
Method: EPA-RCA 8091 (ECD); Procedure: gas chromatograph with electron capture detector; Analyte: 1-chloro-2,4-dinitrobenzene; Matrix: water, soil, and waste matrices; Detection Limit: not provided.|Method: EPA-RCA 8091 (NPD); Procedure: gas chromatograph with nitrogen-phosphorus detection; Analyte: 1-chloro-2,4-dinitrobenzene; Matrix: water, soil, and waste matrices; Detection Limit: not provided.|EMSLC Method 646. The Determination of Dinitro Aromatic Pesticides in Municipal and Industrial Wastewater by Gas Chromatography. Detection limit = 0.001 ug/l.
Fire Hazards -> Reactive - 4th degree
Computed Properties
Molecular Weight:202.55
XLogP3:2.3
Hydrogen Bond Acceptor Count:4
Exact Mass:201.9781343
Monoisotopic Mass:201.9781343
Topological Polar Surface Area:91.6
Heavy Atom Count:13
Complexity:224
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Price Analysis
Recommended Suppliers of 1-Chloro-2,4-dinitrobenzene
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