2,4-Dinitroanilin

1.84 (estimated)

1.9

1.615 at 59 °F (USCG, 1999) - Denser than water; will sink

1.615 g/ml @ 14 °C

1.62 g/cm³

1.615 @25 °C

less than 0.1 mg/mL at 73 °F (NTP, 1992)

SOL IN HOT HYDROCHLORIC ACID

PRACTICALLY INSOL IN COLD WATER; VERY SPARINGLY SOL IN BOILING WATER; 5.8 PARTS SOL IN 100 PARTS 88% ALCOHOL @ 18 °C; 1 PART SOL IN 132.6 PARTS OF 95% ALCOHOL @ 21 °C

Solubility in water: none

435 °F (NTP, 1992)

223 °C

435 °F (CLOSED CUP)

222-224 °C c.c.

349 to 352 °F (NTP, 1992)

187.5-188 °C

187-188 °C

188 °C

6.31 (NTP, 1992) - Heavier than air; will sink (Relative to Air)

6.31 (AIR= 1)

Danger

H300: Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Danger

H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral]

P260, P262, P264, P270, P271, P273, P280, P284, P301+P316, P302+P352, P304+P340, P316, P319, P320, P321, P330, P361+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Chemical: Benzenamine, 2,4-dinitro-

2,4-Dinitroaniline: HSNO Approval: HSR004142 Approved with controls

Special Hazards of Combustion Products: Vapors and combustion gases are irritating

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

A skin, eye, and respiratory tract irritant; Can induce methemoglobinemia; May be absorbed through skin; [ICSC] A skin, eye, and respiratory tract irritant; Oral administration to rats induces methemoglobinemia (weak effect); Inhalation of 17 mg/m3/4hr/day in the first week of pregnancy caused increased embryo mortality and decreased embryo length in rats; Emergency treatment: Aniline; Aniline can induce methemoglobinemia and secondary hemolytic anemia and liver damage. [HSDB] Explosive; A skin and mucous membrane irritant; [CAMEO] Very toxic by inhalation, ingestion, and skin contact; [eChemPortal: ESIS] An irritant; Can be absorbed through skin; May induce methemoglobinemia; [Alfa Aesar MSDS]

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importers, and processors of listed chemical substances and mixtures to submit to EPA copies and lists of unpublished health and safety studies. Benzenamine, 2,4-dinitro- is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

2,4-DINITROANILINE may decompose violently at elevated temperatures. This compound can react with oxidizing materials, i.e. chlorine/hydrochloric acid. (NTP, 1992). In mixture with powdered charcoal ignited upon heating, [Cahiers, 1980, (99), 278].

Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothing

Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower. Refer 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. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Refer for medical attention .

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.

WATER, CARBON DIOXIDE, DRY CHEMICAL

Use water spray, dry chemical, foam, or carbon dioxide. Water or foam may cause frothing. Approach fire from upwind to avoid hazardous vapors and toxic decomposition products. /Nitropropanes/

Store in a cool, dry, well ventilated location. Separate from acids and oxidizing materials. Detached storage must be used.

MATERIALS WHICH ARE TOXIC AS STORED OR WHICH CAN DECOMPOSE INTO TOXIC COMPONENTS ... SHOULD BE STORED IN A COOL WELL VENTILATED PLACE, OUT OF THE DIRECT RAYS OF THE SUN, AWAY FROM AREAS OF HIGH FIRE HAZARD, & SHOULD BE PERIODICALLY INSPECTED. INCOMPATIBLE MATERIALS SHOULD BE ISOLATED ... .

SMALL SPILLS AND LEAKAGE: If a spill of this chemical occurs, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with acetone and transfer the dampened material to a suitable container. Use absorbent paper dampened with acetone to pick up any remaining material. Seal your contaminated clothing and the absorbent paper in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with acetone 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.

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 covered containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.

SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants.

LC50 Pimephales promelas (fathead minnow) 14.2 mg/l/96 hr (Confidence limit 13.5 to 15.0 mg/l). Affected fish lost schooling behavior and swam near the tank surface with half being hyperactive and half hypoactive. They had increased respiration and hemorrhaging, were darkly colored, and lost equilibrium prior to death.

TERRESTRIAL FATE: When released to soil, 2,4-dinitroaniline may undergo covalent chemical bonding with humic materials which can result in its chemical alteration to a latent form and tight adsorption. When covalently bound in this latent form, leaching in soil systems is not generally expected to occur. This covalent bonding proceeds in two steps; a rapid and reversible bonding followed by a slower and much less reversible reaction(1,SRC). Leaching in soil may be possible prior to the occurrence of the slower bonding reaction. In the absence of covalent bonding, moderate leaching may be possible (estimated Koc value of 240)(3,4,SRC). Although one biological screening study showed no biodegradation in river and sea water(2), insufficient data are available to assess the relative importance of biodegradation of 2,4-dinitroaniline in soil(SRC).

AQUATIC FATE: By analogy to the aromatic amine chemical class(2), 2,4-dinitroaniline in the water column may be susceptible to photooxidation via hydroxyl and peroxy radicals(SRC). Aromatic amines have also been shown to undergo covalent bonding with humic materials in the water column and in sediment(1); partitioning from the water column to sediment and suspended material may therefore be important(SRC). Although one biological degradation study found evidence of no microbial degradation(3), insufficient data are available to assess the relative importance of biodegradation of 2,4-dinitroaniline in water. An estimated BCF value of 15(4,SRC) suggests that it will not bioconcentrate significantly in aquatic organisms(SRC). Aquatic hydrolysis and volatilization do not appear to be environmentally important(SRC).

ATMOSPHERIC FATE: Based upon an estimated vapor pressure of 5.94X10-7 mm Hg at 25 °C(1), 2,4-dinitroaniline may exist in both the vapor and the particulate-phase in the ambient atmosphere(2,SRC). It is degraded relatively rapidly in the vapor phase in an average ambient atmosphere by reaction with photochemically produced hydroxyl radicals at an estimated half-life of about 17.7 hr(3,SRC).

Cough. Sore throat.

MAY BE ABSORBED! Redness. Pain.

Redness. Pain.

Aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solution; the initial bonding reaction is followed by a slower and much less reversible reaction believed to represent the addition of the amine to quinoidal structures followed by oxidation of the product to give an amino-substituted quinone; these processes represent pathways by which aromatic amines may be converted to latent forms in the biosphere(3). In the absence of covalent bonding, a Koc of approximately 240 can be estimated for 2,4-dinitroaniline based on an estimated log Kow of 1.84(2) and a recommended regression-derived equation(1,SRC); this Koc value suggests medium soil mobility(4).

Based on an estimated log Kow of 1.84(2), the bioconcentration factor (BCF) for 2,4-dinitroaniline can be estimated to be about 15 from a recommended regression-derived equation(1,SRC). This BCF value suggests that bioconcentration in aquatic organisms may not be significant(SRC).

The Henry's Law constant for 2,4-dinitroaniline can be estimated to be approximately 1.51X10-10 atm-cu m/mole at 25 °C using a chemical structure estimation method(2,SRC). This value of Henry's Law constant suggests that 2,4-dinitroaniline is essentially nonvolatile from water(1).

2,4-DINITROANILINE ADMIN ORALLY TO RATS SHOWED LOW TOXICITY. AFFECTED NERVOUS SYSTEM, CAUSED WEAK MET- & SULF-HEMOGLOBINEMIA, & DECR LEVEL OF THIOL GROUPS IN BLOOD.

THE DNA DAMAGE INDUCED BY IN VIVO ADMINISTRATION OF 2,4-DINITROANILINE WAS DETERMINED ... . THE TARGET ORGANS FOR ULTIMATE CARCINOGENS PRODUCED IN MICE APPEAR TO BE THE LIVER AND THE KIDNEY. THE VALUES OBTAINED AFTER TREATMENT WITH 2,4-DINITROANILINE FALL IN THE RANGE OF CONTROL MICE.

INHALATION OF 17 MG 2,4-DINITROANILINE/CU M FOR 4 HR/DAY WITHIN THE 1ST 19 OR 7 DAYS OF PREGNANCY INCREASED THE MORTALITY OF RAT EMBRYOS FROM 9.9 TO 18.8 AND 25.3%, RESPECTIVELY, AND DECREASED THE EMBRYO LENGTH ON THE 20TH DAY OF PREGNANCY FROM 29.0 TO 24.9 AND 25.2 MM, RESPECTIVELY. THE 7-DAY EXPOSURE ALSO DECREASED THE ALPHA2-GLOBULIN PERCENTAGE FROM 18.6 TO 14.2%. ...

TWO FRAME-SHIFT HISTIDINE MUTANTS (TA1537 AND TA98) AND 2 BASE-PAIR SUBSTITUTED HISTIDINE MUTANTS (TA1535 AND TA100) OF SALMONELLA TYPHIMURIUM WERE EMPLOYED. BOTH THE SPOT TEST AND PLATE-INCORPORATION ASSAY INDICATED THAT /2,4-DINITROANILINE/ WAS MUTAGENIC WITH THREE OF THE TEST STRAINS. ...

For more Non-Human Toxicity Excerpts (Complete) data for 2,4-DINITROANILINE (6 total), please visit the HSDB record page.

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. Benzenamine, 2,4-dinitro- is included on this list.

Section 8(a) of TSCA requires manufacturers of this chemical substance to report preliminary assessment information concerned with production, use, and exposure to EPA as cited in the preamble of the 51 FR 41329.

The disposition of 2,4-dinitroaniline was studied in rats. Male Fisher 344 rats were administered 0 to 90.0 umol/kg (14)C labeled 2,4-dinitroaniline orally or 10.0 umol/kg intravenously. Urine, feces, and bile samples from cannulated rats were analyzed for (14)C activity up to 3 days after pretreatment. Selected rats were killed between 15 minutes and 3 days after dosing and the tissue distribution of 2,4-dinitroaniline was determined. Urine and bile samples were analyzed for metabolites. 2,4-Dinitroaniline was rapidly distributed to all major tissues. Muscle, skin, and adipose tissue contained 65 to 70% of the (14)C activity in the body during the 45 minutes after dosing. Clearance from all tissues was rapid, approximately 70 to 85% of the doses being cleared from most tissues within 6 hours after administration. Three days after administration the major tissues contained very low concentrations of (14)C and variations with dose and route of administration were minimal. Urinary excretion of (14)C activity accounted for 30% of the doses after 6 hours and 63% after 24 hours. Fecal excretion over 3 days accounted for 23% of the dose. Elimination of 2,4-dinitroaniline derived (14)C activity in the bile amounted to 12.5% of the dose after 5 hours. Nine metabolites were detected. 2,4-Dinitrophenylhydroxylamine was the main metabolite. 2,4-Dinitrophenylhydroxylamine was excreted in the urine as the sulfate conjugate and in bile as the glucuronide. /It was/ concluded that 2,4-dinitroaniline appears to have little potential for bioaccumulation in animal tissues. Amine hydroxylation and sulfation of 2,4-dinitroaniline are probable detoxification processes that occur rapidly and facilitate clearance.

Used as an intermediate for azo pigments, toner pigment in printing inks, and corrosion inhibitor; [Hawley]

PREPN OF AZO DYES

... Toner pigment in printing inks, corrosion inhibitor.

(1972) 3.09X10+8 GRAMS (PRINCPL CUSTMS DISTS)

(1975) 5.10X10+7 GRAMS (PRINCPL CUSTMS DISTS)

(1983) 5.02X10+7 g

(1972) GREATER THAN 4.54X10+5 GRAMS

(1974) 2.62X10+8 GRAMS

REACTION OF 2,4-DINITROCHLOROBENZENE WITH AMMONIA

NITRATION OF PARA-NITROANILINE WITH HOT MIXED ACID.