HuagongsheHuagongshe Chemistry Print Report · For research reference only
3-Nitroaniline
M-NITROANILINE · 3-Nitroanilin · Benzenamine, 3-nitro- · Nitranilin · 3-Nitrobenzenamine · 1-AMINO-3-NITROBENZENE · ci37030 · c.i.37030
Identifiers & Physical Properties
| CAS No. | 99-09-2 |
|---|---|
| Molecular formula | C6H6N2O2 |
| Average molar mass | 138.12 g/mol |
| Monoisotopic mass | 138.04292743 g/mol |
| SMILES | Nc1cccc([N+](=O)[O-])c1 |
| InChIKey | XJCVRTZCHMZPBD-UHFFFAOYSA-N |
| PubChem CID | 7423 |
| ChEMBL | CHEMBL14068 |
| EC No. | 202-729-1 |
| DTXSID | DTXSID6025725 |
Chemical & Physical Properties
| XLogP | 1.4 |
|---|---|
| Topological polar surface area | 71.8 |
| Hydrogen bond donors | 1 |
| Hydrogen bond acceptors | 3 |
| Rotatable bonds | 0 |
| Heavy atoms | 10 |
| Formal charge | 0 |
| Complexity | 132 |
| Chemical classes | Nitrogen Compounds -> Nitroanilines |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (partition coefficient) | log Kow = 1.371.43 |
| Odor | Burning sweet odor |
| Density | 0.9011 at 77 °F (NTP, 1992) - Less dense than waterwill float0.9011 at 25 °C/4 °C1.4 g/cm³0.9011 @25 °C0,901 g/cm3 |
| Color/Form | Yellow crystals from waterYELLOW RHOMBIC NEEDLES |
| Solubility | less than 1 mg/mL at 72.5 °F (NTP, 1992)Slightly soluble in benzenesoluble in ethanol, ether, acetonevery soluble in methanolSoluble in chloroform1 g/20 mL alcohol1 g/18 mL ether1 g/11.5 mL methanolIn water, 1,200 mg/L at 24 °CSolubility in water, g/100ml at 25 °C: 0.0891.25g/l1.25 g/L |
| Flash point | 199 °C196 °C |
| Boiling point | 581 to 585 °F at 760 mmHg (decomposes) (NTP, 1992)306 °C, decomposes306.4 °C @760 [mm Hg] |
| Decomposition | When heated to decomp it emits toxic fumes of /nitrogen oxides/.306 °C |
| Melting point | 237 °F (NTP, 1992)114 °CHeat of fusion at melting point = 23.6 kJ/mol111-114 °C (lit.) |
| Vapor pressure | 1 mmHg at 246.7 °F760 mmHg at 582.3 °F (NTP, 1992)0.0000956 [mmHg]9.56X10-5 mm Hg at 25 °CVapor pressure, Pa at 25 °C: 0.0050.0000362 [mm Hg] @25 °C1 mm Hg ( 119 °C) |
| Refractive index | 1.6396 (estimate) |
| Storage conditions | Store below +30°C. |
| Physical state | Crystals, Crystalline Powder and/or Chunks |
| Colour Index | 37030 |
| pKa (acidity coefficient) | 2.466(at 25℃) |
| Specific gravity | 0.901 |
| Color | Yellow to ochre-yellow to orange |
| Specific heat capacity | Cp(crystal): 1.15 J/(g·K), at 25℃ |
| Merck | 14,6581 |
| BRN | 636962 |
| Henry's law constant | 1.93 x 10-5 atmm3/mol at 25 °C (approximate - calculated from water solubility and vapor pressure) |
| InChI | 1S/C6H6N2O2/c7-5-2-1-3-6(4-5)8(9)10/h1-4H,7H2 |
| InChIKey | XJCVRTZCHMZPBD-UHFFFAOYSA-N |
| SMILES | Nc1cccc(c1)[N+]([O-])=O |
| CAS DataBase Reference | 99-09-2(CAS DataBase Reference) |
| EWG's Food Scores | 2 |
| FDA UNII | CM50SM561T |
| NIST Chemistry Reference | m-Nitroaniline(99-09-2) |
| EPA Substance Registry System | m-Nitroaniline (99-09-2) |
| UNSPSC Code | 12352100 |
| NACRES | NA.22 |
| GHS pictogram | GHS06,GHS08 |
| Signal word | Danger |
| GHS hazard statements | H301+H311+H331-H373-H412 |
| GHS precautionary statements | P273-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311-P314 |
| Target organs | Kidney,Liver,Heart,Blood |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges |
| Hazard symbols | T |
| Risk statements (R) | 23/24/25-33-52/53 |
| Safety statements (S) | 28-36/37-45-61-28A |
| UN transport number | UN 1661 (NITROANILINES (o-, m-, p-)) |
| Water hazard class (WGK) | 2 |
| RTECS number | BY6825000 |
| F | 8 |
| Autoignition temperature | 521℃ |
| TSCA inventory status | TSCA listed |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 3STOT RE 2 Oral |
| Packing group | II |
| Customs code | 29214210 |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Hazardous substances data | 99-09-2(Hazardous Substances Data) |
| Toxicity | Acute LD50 for guinea pigs 450 mg/kg, mice 308 mg/kg, quail 562 mg/kg, rats 535 mg/kg (quoted, RTECS, 1985). |
| REACH registrations | Active |
| 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 | DangerH301: Toxic if swallowed [Danger Acute toxicity, oral]P260, P261, P262, P264, P270, P271, P273, P280, P301+P316, P302+P352, P304+P340, P316, P319, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)H301+H311+H331 (97.9%): Toxic if swallowed, in contact with skin or if inhaled [Danger Acute toxicity, oralacute toxicity, dermalacute toxicity, inhalation] |
|---|---|
| Regulatory information | Chemical: Benzenamine, 3-nitro-Status: Active Update: 27-04-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/168803-Nitroaniline: Does not have an individual approval but may be used under an appropriate group standard |
| DOT label | Poison |
| Fire hazards | Flash point data for this chemical are not availablehowever, it is probably combustible. (NTP, 1992)Combustible. Many reactions may cause fire or explosion. Finely dispersed particles form explosive mixtures in air. |
| Health hazards | SYMPTOMS: Symptoms of exposure to this compound may include cyanosis and liver damage. When inhaled or ingested, this compound may cause headache, flushing of the face, difficult breathing, nausea, vomiting, weakness, drowsiness, irritability and dermatitis. Structurally similar chemicals may cause methemoglobinemia. |
| Hazards summary | m-Nitroaniline is in the ACGIH table of Industrial Chemicals for Which Methemoglobin Formation is the Principal Cause of Toxicity. It emits toxic fumes of nitrogen oxides when heated. Methemoglobinemia has been reported after acute exposure and liver injury after chronic exposure. m-Nitroaniline is toxic after ingestion, inhalation, and skin exposure. [HSDB] Can induce methemoglobinemia[ICSC] |
| Reactive group | Nitro, Nitroso, Nitrate, and Nitrite Compounds, Organic |
| EC classification | Symbol: TR: 23/24/25-33-52/53S: (1/2)-28-36/37-45-61Note: C |
| UN classification | UN Hazard Class: 6.1UN Pack Group: II |
| Special Reports | Santodonato J et alMonographs on Human Exposure to Chemicals in the Workplace: Nitroanilines 1-26 (1985). This report summarizes and evaluates toxicologic information relevant to an occupational hazard assessment of nitroanilines, including chemical and physical properties, production and use, extent of occupational exposure, pharmacokinetics, animal carcinogenicity and mutagenicity, and epidemiological studies. |
| 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, 3-nitro, is included on this list. |
| Reactivity Profile | Thermal stability of this compound is reduced by various impurities. This compound may be sensitive to prolonged exposure to light. This compound may react explosively with ethylene oxide at 266 °F. It is incompatible with acids (nitric, sulfuric), acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. (NTP, 1992). Unstable when heated. |
| Chemical Dangers | On combustion, forms toxic fumes of nitrogen oxides. Reacts with strong acids, strong oxidants and strong reducing agents. Reacts with organic materials in the presence of moisture. This generates fire hazard. |
| Fire fighting | Fires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. A water spray may also be used. (NTP, 1992)Use water spray, powder, foam, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. |
| First aid measures | Fresh air, rest. Artificial respiration may be needed. 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.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 acids, strong oxidants, combustible substances, reducing agents and food and feedstuffs. Dry. |
| Exposure control and personal protection | Biological Exposure Indices (BEI) [ACGIH] - Methemoglobin in blood = 1.5% of hemoglobin during or at end of shift. [ACGIH] |
| Fire fighting procedures | In case of fire: keep drums, etc., cool by spraying with water. Combat fire from a sheltered position. Powder, water spray, foam, carbon dioxide.If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use water foam, dry chemical, or carbon dioxide. /Nitroanilines/Wear positive pressure self-contained breathing apparatus when fighting fires involving this material. /Nitroanilines/ |
| Storage conditions | Protect against physical damage to containers and prevent from moisture contacts. |
| Cleanup methods | 1. Ventilate area of spill. 2. For small quantities, sweep onto paper or other suitable material, place in an appropriate container & burn in a safe place (such as a fume hood). Large quantities may be reclaimedhowever, if this is not practical, dissolve in a flammable solvent (such as alcohol) & atomize in a suitable combustion chamber equipped with an appropriate effluent gas cleaning device. /Nitroaniline/ |
| Nonfire spill response | SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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. |
| Disposal methods | SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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 qualitypotential migration in soil or watereffects on animal, aquatic, and plant lifeand conformance with environmental and public health regulations. |
| 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. |
| Preventive Measures | PREVENT DISPERSION OF DUST! Do not eat, drink, or smoke during work. Wash hands before eating.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.AVOID BREATHING DUSTAVOID CONTACT WITH SKIN, EYES, CLOTHING.SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.For more Preventive Measures (Complete) data for 3-NITROANILINE (7 total), please visit the HSDB record page. |
| Ecotoxicity values | LC50 Oryzias ladipes (Orange-red killfish) 158 mg/L/24 hr, 71 mg/L/48 hr, 69 mg/L/72 hr, 67 mg/L/96 hrsemi-static.LC50 Oryzias ladipes (Orange-red killfish) 96 mg/L/48 hoursEC50Species: Chlorella pyrenoidosa (Green algae, 2x10+6 cell/mL)Conditions: freshwater, static, 22 °C, pH 7.4Concentration: 58000 ug/L for 72 hrEffect: population growth inhibition />98% purity/Species: Daphnia magna (Water flea, 24 hr)Conditions: freshwater, static, 18-20 °C, pH 8.0-8.3, dissolved oxygen 8.1-9.7 mg/LConcentration: 6770 ug/L for 24 hr (95% confidence interval: 3990-11000 ug/L)Effect: intoxication, immobilization />98% purity/For more Ecotoxicity Values (Complete) data for 3-NITROANILINE (12 total), please visit the HSDB record page. |
| Environmental fate | TERRESTRIAL FATE: Based on a classification scheme(1), Koc values of 44(2) and 87(3), indicate that 3-nitroaniline is expected to have very high to high mobility in soil(SRC). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(7,8), suggesting that mobility may be much lower in some soils(SRC). Volatilization of 3-nitroaniline from moist soil surfaces is not expected to be an important fate process(SRC) given a Henry's Law constant of 7.9X10-9 atm-cu m/mole(4). 3-Nitroaniline is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 9.56X10-5 mm Hg(5). 3-Nitroaniline was determined to be non-biodegradable using the Japanese MITI protocol(6), indicating that biodegradation is not an important environmental fate process in soil(SRC).AQUATIC FATE: Based on a classification scheme(1), Koc values of 44(2) and 87(3) indicate that 3-nitroaniline is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon a Henry's Law constant of 7.9X10-9 atm-cu m/mole(5). According to a classification scheme(6), BCFs of <10(7,8), suggest bioconcentration in aquatic organisms is low(SRC). 3-Nitroaniline is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Aromatic amines react relatively rapidly in natural water with photochemically produced oxidants such as hydroxyl radicals and alkoxy radicals(9)half-lives of aniline are on the order of 30 hr of sunlight for hydroxyl radicals and 19 hr of sunlight for alkoxy radicals(9)reactions with 3-nitroaniline are likely to be somewhat slower due to the presence of the nitro function(SRC). 3-Nitroaniline was determined to be non-biodegradable using the Japanese MITI protocol(8), indicating that biodegradation is not an important environmental fate process in water(SRC).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 3-nitroaniline, which has a vapor pressure of 9.56X10-5 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 3-nitroaniline 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 41 hours(SRC), calculated from its rate constant of 9.4X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 3-nitroaniline may be removed from the air by wet or dry deposition(SRC). 3-Nitroaniline does absorb light at wavelengths >290 nm(4) and therefore may be susceptible to direct photolysis by sunlight(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 vapour, through the skin and by ingestion. |
| Ecotoxicity excerpts | /AQUATIC SPECIES/ The LC50 (96 hr) values and the bioconcentration factors (BCF) for nine anilines (aniline2-, 3-, 4-chloroaniline2-, 3-, 4-nitroaniline2,4- and 3,4-dichloroaniline) in the zebrafish (Brachydanio rerio) were determined. Biotransformation products of anilines in the zebrafish were analyzed by HPLC. The aim of the investigations was to find relationships between accumulation/elimination/metabolism and toxicity on the one hand and between chemical structure and biotransformation on the other. ... A good correlation of log BCF and of log Pow with log LC50 /was found/. This concurs with the assumption that the internal dose determines the toxicological effect. All anilines investigated, with the exception of 2- and 4-nitroaniline, were transformed into the corresponding acetanilides. The toxicity of the compounds was not altered by biotransformation. ... |
| Signs and Symptoms | Blue lips, fingernails and skin. Headache. Dizziness. Nausea. Confusion. Convulsions. Laboured breathing. Unconsciousness.MAY BE ABSORBED! Further see Inhalation.Further see Inhalation. |
| Effluent Concentrations | Raw wastewater collected from a US dye manufacturing plant on the Black River in July 1976 contained 270 ppb nitroaniline (isomers unspecified)the final treated effluent contained no detectable levels of nitroaniline(1). |
| ICSC Environmental Data | The substance is harmful to aquatic organisms. |
| Medical Surveillance | Routine checking of lips, tongue, and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular, or pulmonary diseases.Consider the points of attack (blood, heart, lungs and liver) in preplacement and periodic physical examinations. /4-Nitroaniline/Routine checking of lips, tongue and nail beds of exposed personnel for signs of cyanosis. /Protect/ from exposure those individuals with anemia, cardiovascular or pulmonary diseases. |
| Soil Adsorption/Mobility | Soil adsorption studies using four silt loam soils and a 2-hour adsorption period determined a mean log Kom of 1.70 which corresponds to a Koc of 87 for 3-nitroaniline(1). 3-Nitroaniline had a measured log Koc of 1.64 which corresponds to a Koc value of 44(2). According to a classification scheme(3), these Koc values suggest that 3-nitroaniline is expected to have very high to high mobility in soil(SRC). 3-Nitroaniline was found to have a Kd value of 3.5 L/kg in homoionic K+ Montmorillonite type soil(4). However, anilines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC). |
| Human Toxicity Excerpts | /SIGNS AND SYMPTOMS/ Acute exposure can cause methemoglobinemia, cyanosis. Chronic exposure may cause liver damage/SIGNS AND SYMPTOMS/ Symptomatology: 1. Lips, tongue, and mucous membranes navy blue to blackskin slate gray, all without signs of cardiac or pulmonary insufficiency. 2. Severe headache, nausea, sometimes vomiting, dryness of throat. 3. Central nervous symptoms: confusion, ataxia, vertigo, tinnitus, weakness, disorientation, lethargy, drowsiness, and finally, coma. Convulsions may occur but appear to be uncommon. 4. Cardiac effects: heart blocks, arrhythmias, and shock. 5. Death, although uncommon, is usually due to cardiovascular collapse and not resp paralysis. 6. Urinary signs and symptoms may incl painful micturition, hematuria, hemoglobinuria, and renal insufficiency (usually mild). 7. A late acute hemolytic episode should be anticipated at 6 to 8 days after ingestion. /Aniline//OTHER TOXICITY INFORMATION/ ... Powerful methemoglobin former with attendant hemolytic effect../OTHER TOXICITY INFORMATION/ On prolonged and excessive exposures it may ... cause liver damage. ... Its vapors are highly toxic as well. |
| Artificial Pollution Sources | 3-Nitroaniline's production and use as an intermediate in the synthesis of dyes and pigments(1) may result in its release to the environment through various waste streams(SRC). |
| F | 8 |
| Personal protective equipment (PPE) | Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges |
| Water hazard class (WGK) | 2 |
| TSCA inventory status | TSCA listed |
| RTECS number | BY6825000 |
| UN transport number | UN 1661 (NITROANILINES (o-, m-, p-)) |
| Customs code | 29214210 |
| Toxicity | Acute LD50 for guinea pigs 450 mg/kg, mice 308 mg/kg, quail 562 mg/kg, rats 535 mg/kg (quoted, RTECS, 1985). |
| Risk statements (R) | 23/24/25-33-52/53 |
| Signal word | Danger |
| GHS pictogram | GHS06,GHS08 |
| Hazard symbols | T |
| Safety statements (S) | 28-36/37-45-61-28A |
| Hazard class | 6.1Acute Tox. 3 DermalAcute Tox. 3 InhalationAcute Tox. 3 OralAquatic Chronic 3STOT RE 2 Oral |
| Storage class | 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials |
| Packing group | II |
| Target organs | Kidney,Liver,Heart,Blood |
| GHS hazard statements | H301+H311+H331-H373-H412 |
| Limited quantities | 0.5 Kg (solid) |
| Excepted quantities | Max Inner Pack (1g or 1ml) and Max Outer Pack (500g or 500ml) |
| REACH registrations | Active |
| Autoignition temperature | 521℃ |
| GHS precautionary statements | P273-P280-P301+P310+P330-P302+P352+P312-P304+P340+P311-P314 |
| Hazardous substances data | 99-09-2(Hazardous Substances Data) |
Applications & Uses
Uses
Dyestuff intermediate. Acetylation of 3-nitroaniline followed by reduction gives 3-aminoacetanilide. Diazotization, followed by reduction of the diazosulfonate with ammonium bisulfite and subsequent hydrolysis, gives (3-nitrophenyl) hydrazine; an intermediate in the production of pyrazolone azo coupling components. 3-Nitroaniline is used as a diazo component (Fast Orange R Base) in azo dyes (e.g., C.I. Disperse Yellow 5 and C.I. Acid Orange 18).
Uses
3-Nitroaniline is commonly used as a raw material for dyes. It is also used as a chemical intermediate for azo coupling component 17 and the dyes disperse yellow 5 and acid blue 29. The chemical is changed to other substances (dyestuffs and m-nitrophenol) during the dyeing process.
General Description
Yellow needles or yellow powder.
Preparation & Synthesis
Preparation
M-nitroaniline partial reduction.