HuagongsheHuagongshe Chemistry Print Report · For research reference only
2,4-Dinitroaniline
2,4-Dinitroaniline,~99% · 2.4-Dinitr · 2,4-DinitroaniL · 2,4-Nitroaniline · 4-Dinitroaniline · 2,4-Dinitraniline · 2,4-Dinitroanilin · dinitro-2,4aniline
Identifiers & Physical Properties
| CAS No. | 97-02-9 |
|---|---|
| Molecular formula | C6H5N3O4 |
| Average molar mass | 183.12 g/mol |
| Monoisotopic mass | 183.02800564 g/mol |
| SMILES | Nc1ccc([N+](=O)[O-])cc1[N+](=O)[O-] |
| InChIKey | LXQOQPGNCGEELI-UHFFFAOYSA-N |
| PubChem CID | 7321 |
| ChEMBL | CHEMBL354318 |
| ChEBI | CHEBI:34242 |
| EC No. | 202-553-5 |
| DTXSID | DTXSID1021823 |
Chemical & Physical Properties
| XLogP | 1 |
|---|---|
| Topological polar surface area | 118 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 0 |
| Heavy atoms | 13 |
| Formal charge | 0 |
| Complexity | 221 |
| Chemical classes | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | Chemical shift |
| LogP (partition coefficient) | 1.84 (estimated)1.9 |
| Odor | Musty odor |
| Density | 1.615 at 59 °F (USCG, 1999) - Denser than waterwill sink1.615 g/ml @ 14 °C1.62 g/cm³1.615 @25 °C1,61 g/cm3 |
| Color/Form | YELLOW NEEDLES FROM DIL ACETONE, GREENISH-YELLOW PLATES FROM ALCOHOL. |
| Solubility | less than 0.1 mg/mL at 73 °F (NTP, 1992)SOL IN HOT HYDROCHLORIC ACIDPRACTICALLY INSOL IN COLD WATERVERY SPARINGLY SOL IN BOILING WATER5.8 PARTS SOL IN 100 PARTS 88% ALCOHOL @ 18 °C1 PART SOL IN 132.6 PARTS OF 95% ALCOHOL @ 21 °CSolubility in water: noneDMSO (Slightly), Methanol (Slightly)0.06 g/L (20 ºC) |
| Flash point | 435 °F (NTP, 1992)223 °C435 °F (CLOSED CUP)222-224 °C c.c. |
| Boiling point | 56.7 °C316.77°C (rough estimate) |
| Decomposition | WHEN HEATED TO DECOMP, IT EMITS HIGHLY TOXIC FUMES. |
| Melting point | 349 to 352 °F (NTP, 1992)187.5-188 °C187-188 °C177 °C |
| Vapor density | 6.31 (NTP, 1992) - Heavier than airwill sink (Relative to Air)6.31 (AIR= 1) |
| Bulk density | 800kg/m3 |
| Vapor pressure | <0.001 hPa ( 25 °C) |
| Refractive index | 1.6910 (estimate) |
| Storage conditions | Flammables area |
| pKa (acidity coefficient) | pK1:-14.25(+1) (25°C) |
| Physical state | Crystalline Powder |
| Color | Yellow to yellow-green or yellow-brown |
| pH | 7 (1g/L in H2O) |
| Merck | 14,3270 |
| BRN | 982999 |
| Henry's law constant | 6.5×104 mol/(m3Pa) at 25℃, HSDB (2015) |
| Stability | Stable. Incompatible with oxidizing agents. May decompose violently at elevated temperatures. |
| InChI | 1S/C6H5N3O4/c7-5-2-1-4(8(10)11)3-6(5)9(12)13/h1-3H,7H2 |
| InChIKey | LXQOQPGNCGEELI-UHFFFAOYSA-N |
| SMILES | Nc1ccc(cc1[N+]([O-])=O)[N+]([O-])=O |
| CAS DataBase Reference | 97-02-9(CAS DataBase Reference) |
| EWG's Food Scores | 1-2 |
| FDA UNII | 5BI780R6W6 |
| NIST Chemistry Reference | Benzenamine, 2,4-dinitro-(97-02-9) |
| EPA Substance Registry System | 2,4-Dinitroaniline (97-02-9) |
| UNSPSC Code | 41116107 |
| NACRES | NA.22 |
| GHS pictogram | GHS06,GHS08,GHS09 |
| Signal word | Danger |
| GHS hazard statements | H300+H310+H330-H373-H411 |
| GHS precautionary statements | P262-P264-P273-P280-P302+P352+P310-P304+P340+P310 |
| Hazard symbols | T+,N |
| Risk statements (R) | 26/27/28-33-51/53 |
| Safety statements (S) | 28-36/37-45-61-28A |
| UN transport number | UN 1596 (DINITROANILINES) |
| Water hazard class (WGK) | 2 |
| RTECS number | BX9100000 |
| Autoignition temperature | >365°C |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 1 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralAquatic Chronic 2STOT RE 2 |
| Packing group | II |
| Customs code | 29214210 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Hazardous substances data | 97-02-9(Hazardous Substances Data) |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
Safety & Regulations
| GHS classification | DangerH300: 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)H300 (100%): Fatal if swallowed [Danger Acute toxicity, oral] |
|---|---|
| Regulatory information | Chemical: Benzenamine, 2,4-dinitro-2,4-Dinitroaniline: HSNO Approval: HSR004142 Approved with controls |
| DOT label | Poison |
| Fire hazards | Special Hazards of Combustion Products: Vapors and combustion gases are irritatingCombustible. Gives off irritating or toxic fumes (or gases) in a fire. |
| Fire potential | SLIGHT, WHEN EXPOSED TO HEAT OR FLAME. |
| Health hazards | May cause headache, nausea, stupor. Irritating to skin and mucous membrane. (USCG, 1999) |
| Hazards summary | A skin, eye, and respiratory tract irritantCan induce methemoglobinemiaMay be absorbed through skin[ICSC] A skin, eye, and respiratory tract irritantOral 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 ratsEmergency treatment: AnilineAniline can induce methemoglobinemia and secondary hemolytic anemia and liver damage. [HSDB] ExplosiveA skin and mucous membrane irritant[CAMEO] Very toxic by inhalation, ingestion, and skin contact[eChemPortal: ESIS] An irritantCan be absorbed through skinMay induce methemoglobinemia[Alfa Aesar MSDS] |
| Reactive group | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| EC classification | Symbol: T+, NR: 26/27/28-33-51/53S: (1/2)-28-36/37-45-61 |
| UN classification | UN Hazard Class: 6.1UN Pack Group: II |
| TSCA requirements | 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. |
| Reactivity Alerts | Explosive |
| Reactivity Profile | 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 fighting | Fire Extinguishing Agents Not to Be Used: Water or foam may cause frothingUse water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. |
| First aid measures | 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 . |
| First aid | 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. |
| Safe storage | Separated from strong oxidants and food and feedstuffs. Well closed. |
| Fire fighting procedures | WATER, CARBON DIOXIDE, DRY CHEMICALUse 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/ |
| Storage conditions | 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 ... . |
| Nonfire spill response | 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. |
| Spillage disposal | 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. |
| Preventive Measures | 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. |
| Isolation and Evacuation | Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]: |
| Eye Prevention | Wear safety goggles. |
| Fire Prevention | NO open flames. |
| Ecotoxicity values | 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. |
| Environmental fate | 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 stepsa 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). |
| Adverse effects | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation. |
| Exposure routes | The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion. |
| Signs and Symptoms | Cough. Sore throat.MAY BE ABSORBED! Redness. Pain. |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Soil Adsorption/Mobility | Aromatic amines have been observed to undergo rapid and reversible covalent bonding with humic materials in aqueous solutionthe 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 quinonethese 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). |
| Artificial Pollution Sources | 2,4-Dinitroaniline may be released to the environment during its production and use in the preparation of azo dyes(1,SRC). |
| Environmental Biodegradation | 2,4-Dinitroaniline at an initial concn of 100 ppm showed no biodegradation in river and sea water after 3 days using a cultivation test method(1). |
| Environmental Bioconcentration | 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). |
| Volatilization from Water/Soil | 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). |
| Non-Human Toxicity Excerpts | 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. |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | BX9100000 |
| UN transport number | UN 1596 (DINITROANILINES) |
| Customs code | 29214210 |
| Risk statements (R) | 26/27/28-33-51/53 |
| Signal word | Danger |
| GHS pictogram | GHS06,GHS08,GHS09 |
| Hazard symbols | T+,N |
| Safety statements (S) | 28-36/37-45-61-28A |
| Hazard class | 6.1Acute Tox. 1 DermalAcute Tox. 2 InhalationAcute Tox. 2 OralAquatic Chronic 2STOT RE 2 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | II |
| GHS hazard statements | H300+H310+H330-H373-H411 |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
| Autoignition temperature | >365°C |
| GHS precautionary statements | P262-P264-P273-P280-P302+P352+P310-P304+P340+P310 |
| Hazardous substances data | 97-02-9(Hazardous Substances Data) |
Applications & Uses
Uses
2,4-Dinitroaniline is a nitro substituted benzamide derivative with anti-inflammatory activities in vitro.
General Description
Yellow powder or crystals with a musty odor. Sinks in water.