| Use | AS A REAGENT FOR THE DETECTION &
DETERMINATION OF NICOTINIC ACID, NICOTINAMIDE AND OTHER PYRIDINE
CMPD. [R2]
DYES; ORGANIC SYNTHESIS [R1]
ALGICIDE IN COOLANT WATER OF AIR CONDITIONING SYSTEMS.
[R8]| Apparent Color | Yellow crystals
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| Odor | Almond odor
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| Boiling Point | 315 DEG C
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| Melting Point | 54 DEG C
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| Molecular Weight | 202.56
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| Misc | DENSITY: 1.7
SOLUBILITY: IN ETHER, BENZENE & CARBON DISULFIDE; SPARINGLY SOL IN
COLD, FREELY SOL IN HOT ALC; Water solubility: 8 mg/l at 15 deg C
SADTLER REF NUMBER: 964 (IR, PRISM); 196 (IR, GRATING); INDEX OF
REFRACTION: 1.5857 @ 60 DEG C/D; IR: 347 (Coblentz Society Spectral Collection); UV:
5204 (Sadtler Research Laboratories Spectral Collection); MASS: 164 (Aldermaston, Eight Peak
Index of Mass Spectra, UK)
6.98 (air=1)
MELTING POINT: 43 DEG C /BETA FORM, UNSTABLE/
MP: 27 DEG C /GAMMA FORM, UNSTABLE/
DENSITY OR SP GR : 1.6867 @ 16 DEG C /BETA FORM/; MELTING POINT: 53 DEG C
/ALPHA FORM, STABLE/
YELLOW RHOMBIC CRYSTALS /ALPHA FORM/
YELLOW RHOMBIC CRYSTALS FROM ETHER, NEEDLES FROM ALCOHOL /BETA
FORM/
PRIMARY IRRITANT; SEVERE ALLERGIC DERMATITIS IN ALMOST EVERYONE
AFTER REPEATED SKIN CONTACT. SYSTEMIC ACTIONS INCLUDE
METHEMOGLOBINEMIA. MORE TOXIC THAN NITROCHLOROBENZENE. [R16]
... 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/ ... .
[R17]
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. [R17]
THE REACTION /TO DINITROCHLOROBENZENES/ MAY VARY FROM A SMALL
AREA OF PRURITIC VESICULOPAPULAR ERUPTION TO A GENERALIZED
EXFOLIATIVE DERMATITIS. [R18]
SKIN REACTIVITY TO DNCB WAS EVALUATED IN 94 HEALTHY TERM NEONATES,
AGED 1-30 DAYS & IN 190 INFANTS (2-9 MO). INITIAL DOSE OF 1 MG & CHALLENGE
OF 0.1 MG WERE USED. SENSITIZATION WAS INDUCED IN 6.7% IN 1ST 15 DAYS OF
LIFE, 25.7% BY 1ST MO, 63% IN 3RD MO, & TO 91% IN 9TH MO. [R19]
TOXIC BY INGESTION, INHALATION, AND SKIN ABSORPTION. [R1]
MAY CAUSE DERMATITIS OF BOTH PRIMARY AND ALLERGIC TYPES. [R2]
/IT/ IS OF LITTLE IMPORTANCE AS A SYSTEMIC POISON, ALTHOUGH IT IS ALMOST
A UNIVERSAL SENSITIZER, CAUSING CONTACT DERMATITIS IN FROM 60 TO 80%
OF INDIVIDUALS HAVING EVEN MINUTE CONTACT WITH IT. [R8]
A chemical plant, where an increased number of non-Hodgkin's lymphomas and myelomas had
been observed, was monitored for genotoxic effects occurring in peripheral mononuclear
leukocyte samples from 76 exposed workers. Biochemical markers sensitive to DNA repair and
drug metabolism were used as the indicators of genotoxic risk. Unscheduled DNA synthesis
(UDS) and covalent binding induced by N-acetoxy-N-acetyl-2-aminofluorene (NA-AAF) and
constitutive and gamma ray induced adenosine diphosphate ribosyl transferase (ADPRT) activities
were highly and significantly elevated over the corresponding values for a control group of 48
postal workers. Microsomal and soluble epoxide hydrolases and glutathione transferase activities
directed towards trans-stilbene oxide and 1-chloro-2,4-dinitrobenzene were not significantly
altered in the exposed group. The exposure in this factory was complex, involving over 100
chemicals including several well known carcinogens. However, no apparent significant
associations to exposure could be established. [R20]
IN THE SALMONELLA/MICROSOME TEST, DNCB WAS MUTAGENIC FOR TA100,
TA1538, & TA98 STRAINS. [R21]
SEVEN DAILY PAINTINGS OF 1 MG DNCB TO GUINEA PIG EAR STIMULATED THE
EAR LEUCINE AMINOPEPTIDASE, SUGGESTING ACTIVATION OF LYSOSOMAL
CATABOLISM. [R22]
EXPOSURE OF ADULT FEMALE RATS TO 1 ML SOLN, TWICE WEEKLY OVER 1 WK,
DID NOT INFLUENCE CYTOCHROME P450 SYSTEM OR ENZYME ACTIVITIES IN
LIVER & SKIN MICROSOMES. DNCB (1-100 UG/PLATE) WAS MUTAGENIC IN
SALMONELLA/MICROSOME TEST WITH & WITHOUT MAMMALIAN METABOLIZING
SYSTEM. [R23]
2,4-DINITROCHLOROBENZENE WAS INACTIVE /IN TUMOR INDUCTION AFTER
12-13 MONTHS/ AFTER DIETARY ADMIN TO MALE CHARLES RIVER RATS & MALE
& FEMALE HAM/ICR MICE. [R24]
THE MUTAGENICITY OF CDNB IN SALMONELLA TYPHIMURIUM TESTER STRAINS
TA1535, TA100, TA1538 & TA98 WAS DRASTICALLY LOWERED IN PRESENCE OF S9
FRACTION BUT NOT IN PRESENCE OF MICROSOMES. PRESENCE OF GSH &
GSH-TRANSFERASES IN S9 FRACTIONS DECREASED &/OR ABOLISHED THE
MUTAGENICITY. [R25]
Age associated alterations of hepatic cytosolic glutathione S-transferase activities towards
1-chloro-2,4-dinitrobenzene and 1,2-dichloro-4-nitrobenzene were investigated in Brown Norway
rats of both sexes (11-144 weeks old), under control conditions and after administration of
phenobarbital. With both substrates, small changes in glutathione S-transferase activities are
observed for the control rats (15-53 weeks old). For these specific age groups, male glutathione
S-transferase activities are significantly higher than those of their female counterparts, with sex
related differences being most pronounced after 1,2-dichloro-4-nitrobenzene conjugation. Using
1-chloro-2,4-dinitrobenzene as a general substrate, the sex differences tend to decrease from the
age of 53 weeks onwards to become non-significant at the age of 112 weeks. Phenobarbital
administration significantly increases the total and the isoenzymes 3-3 and 3-4 activities in both
sexes, with the highest and the lowest increase being observed in the youngest and oldest animals,
respectively. It therefore can be concluded that some age related variations exist as far as the
glutathione S-transferase activity of both control and phenobarbital treated rats are concerned, but
that the changes observed are rather small. On the contrary, the parameters sex and phenobarbital
treatment are found to be responsible for the major activity changes observed. [R26]
LD50 Rat oral 1.07 g/kg [R2]
Nitrobenzene is readily absorbed by contact with the skin, inhalation of the vapor, or by ingestion.
... Nitrobenzene is also readily absorbed through the lung, which can retain up to 80% of the
chemical. ... /Nitrobenzene/ [R27]
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.
[R28]
YIELDS S-(4-CHLORO-3-NITROPHENYL)GLUTATHIONE IN TICKS, LOCUST,
HOUSEFLIES, GRASS GRUBS AND PIGEONS /FROM TABLE/ [R29]
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. [R30]
DIETARY 2(3)-TERT-BUTYL-4-HYDROXYANISOLE (BHA) CAUSED INCREASES IN
MOUSE & RAT HEPATIC GLUTATHIONE S-TRANSFERASE (EC 2.5.1.18) SPECIFIC
ACTIVITIES WITH 1-CHLORO-2,4-DINITROBENZENE. [R31]
1-Chloro-2,4-dinitrobenzene can be released to the environment in waste streams from the
production of azo and sulfur dyes. If released to water, some 1-chloro-2,4-dinitrobenzene may
partition to sediment. Volatilization from water is not expected to be an environmentally
significant fate process (volatilization half-life of approximately 166 days from a model river).
Data are available suggesting that it may not biodegrade in water systems; however, data are
limited. In soil, its Koc of about 1,390 suggests low soil mobility. No data are available on other
potential degradation processes in soil or water. If released to the atmosphere, vapor phase
1-chloro-2,4-dinitrobenzene is degraded slowly by reaction with photochemically produced
hydroxyl radicals (estimated half-life of 2 yrs in air). In occupational settings, exposure may occur
through inhalation of vapors or through eye and skin contact. (SRC)
1-Chloro-2,4-dinitrobenzene is used primarily in the manufacture of azo dyes; other areas include
the manufacture of fungicides, rubber chemicals and explosives(1). It has been qualitatively
detected in water effluent from sulfur dye production(2), which suggests that it is released to the
environment during its production and use in the manufacture of azo and sulfur dyes(SRC). [R33]
TERRESTRIAL FATE: The estimated Koc of approximately 1390(1,SRC) indicates that
1-chloro-2,4-dinitrobenzene would probably have low mobility in soil(2,SRC). No data are
available regarding biodegradation or other chemical processes in soil(SRC). [R34]
AQUATIC FATE: If released to water, 1-chloro-2,4-dinitrobenzene will not evaporate
significantly into the atmosphere based on an estimated volatilization half-life of approximately
166 days from a model river(1,SRC). Based on the estimated Koc of about 1,390(1,SRC),
1-chloro-2,4-dinitrobenzene may partition from the water column to sediment(SRC). Hydrolysis
in water is not expected to be an environmentally significant fate process(1,SRC). One
biodegradation test in water reported 1-chloro-2,4-dinitrobenzene as being non-biodegradable(2).
No data are available on other potential degradation processes in water. [R35]
ATMOSPHERIC FATE: Vapor-phase 1-chloro-2,4-dinitrobenzene is degraded slowly in the
ambient atmosphere by reaction with photochemically formed hydroxyl radicals; the half-life for
this reaction in typical air can be estimated to be about 2 yrs(1,SRC). [R36]
BIOD: 1-Chloro-2,4-dinitrobenzene is reported as non-biodegradable in water based on an
aqueous screening biodegradation test using 100 ppm as an initial concn, activated sludge
inoculum and a 2 week incubation period(1). [R37]
ABIO: The rate constant for the vapor-phase reaction of 1-chloro-2,4-dinitrobenzene with
photochemically produced hydroxyl radicals has been estimated to be 2.17X10-14 cu
cm/molecule-sec at 25 deg C which corresponds to an atmospheric half-life of about 2 yrs at an
atmospheric concn of 5X10+5 hydroxyl radicals per cu cm(1,SRC). Aromatic nitro compounds
and halogenated aromatics are generally resistant to hydrolysis(2); therefore, hydrolysis is not
expected to be significant(SRC). [R38]
Based on a measured water solubility of 8 mg/L at 15 deg C(2), the bioconcentration factor
(BCF) for 1-chloro-2,4-dinitrobenzene can be estimated to be about 191 from a recommended
regression-derived equation(1,SRC). [R39]
Based on a measured water solubility of 8 mg/L at 15 deg C(1) and a recommended regression
derived equation(2), a Koc of approximately 1390 can be estimated(SRC). This Koc value
suggests that 1-chloro-2,4-dinitrobenzene will have low soil mobility(3). [R40]
The Henry's Law constant for 1-chloro-2,4-dinitrobenzene can be estimated to be approximately
3.15X10-7 atm-cu m/mole at 25 deg C using a chemical structure estimation method(2,SRC).
This value of Henry's Law constant suggests that 1-chloro-2,4-dinitrobenzene will volatilize
slowly from water(1). Based on this value, the volatilization half-life of
1-chloro-2,4-dinitrobenzene from a model river 1 m deep flowing 1 m/sec with a wind velocity of
3 m/sec has been estimated to be approximately 166 days(1,SRC). [R41]
SURFACE WATER: 1-Chloro-2,4-dinitrobenzene has been detected in the Rhine river at concns
of <0.01 ug/L in 1978 and 1979(1). [R42]
1-Chloro-2,4-dinitrobenzene has been qualitatively detected in water effluent from sulfur dye
production(1). [R43]
1-Chloro-2,4-dinitrobenzene is used primarily in the manufacture of azo dyes; other areas include
the manufacture of fungicides, rubber chemicals and explosives(1). It has been qualitatively
detected in water effluent from sulfur dye production(2). Therefore, workers involved in the
preparation of these dyes and other chemicals may be exposed through inhalation of vapors or
through eye and skin contact(SRC). [R33]
In industrial exposure ... /skin/ contact. [R8]
NIOSH (NOHS Survey 1972-1974) has statistically estimated that 3,015 workers are exposed to
1-chloro-2,4-dinitrobenzene in the USA(1). NIOSH (NOES Survey 1981-1983) has statistically
estimated that 170 workers are exposed to 1-chloro-2,4-dinitrobenzene in the USA(2). [R44]
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