ChemicalBook > Product Catalog > Organic Chemistry > Amides > Naphthenic amines derivatives > 4-Nitroaniline
4-Nitroaniline Chemical Properties
- Melting point:147 °C
- Boiling point:332 °C
- Density 1,437 g/cm3
- vapor density 4.77 (vs air)
- vapor pressure 1.33 hPa (142 °C)
- refractive index 1.6465 (estimate)
- Flash point:329 °F
- storage temp. Store at R.T.
- solubility ethanol: soluble25mg/mL, slightly hazy, yellow to brownish-yellow
- form crystalline
- Colour Index 37035
- pka1(at 25℃)
- color yellow
- Specific Gravity1.437
- OdorAmmonia odor
- PH Range7
- Water Solubility 0.8 g/L (20 ºC)
- Merck 14,6584
- BRN 508690
- Henry's Law Constant1.15 x 10-9 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999)
- Exposure limitsNIOSH REL: TWA 3; IDLH 300; OSHA PEL: TWA 6; ACGIH TLV: TWA 3 (adopted).
- Stability:Stable. Incompatible with sodium hydroxide, strong oxidizing agents, strong reducing agents. May attack some plastics, rubber and coatings. May decompose explosively in the presence of initiators. Moisture sensitive. May be light and air-sensitive.
- CAS DataBase Reference100-01-6(CAS DataBase Reference)
- NIST Chemistry Referencep-Nitroaniline(100-01-6)
- EPA Substance Registry Systemp-Nitroaniline (100-01-6)
- Hazard Codes T,F
- Risk Statements 23/24/25-33-52/53-39/23/24/25-11
- Safety Statements 28-36/37-45-61-28A-16-1/2-7
- RIDADR UN 1661 6.1/PG 2
- WGK Germany 2
- RTECS BY7000000
- F 8
- Autoignition Temperature500 °C
- Hazard Note Toxic
- TSCA Yes
- HazardClass 6.1
- PackingGroup II
- HS Code 29214210
- Hazardous Substances Data100-01-6(Hazardous Substances Data)
- ToxicityAcute LD50 for wild birds 75 mg/kg, guinea pigs 450 mg/kg, mice 810 mg/kg, quail 1,000 mg/kg, rats 750 mg/kg (quoted, RTECS, 1985).
4-Nitroaniline Usage And Synthesis
- Chemical PropertiesYellow fine crystals
- Chemical Propertiesp-Nitroaniline consists of yellow crystals with a pungent, faint ammonia-like odor.
- Physical propertiesBright yellow crystalline powder or flakes with a faint, ammonia-like, slightly pungent odor. Combustible.
- UsesProduct of chromogenic reactions.
- Uses4-Nitroaniline is used in the synthesis of photorefractive polymers, as novel chromophores in analytical study. As well, due to the absorption spectrum associated with 4-Nitroaniline, it is used to de termine catechol derivatives in syntheses.
- UsesDyestuff intermediate.
- DefinitionChEBI: A nitroaniline carrying a nitro group at position 4.
- General DescriptionYellow solid with a mild odor. Sinks in water.
- Air & Water Reactions4-Nitroaniline may be sensitive to prolonged exposure to air and light. Insoluble in water. 4-Nitroaniline is sensitive to moisture.
- Reactivity ProfileP-NITROANILINE may react vigorously with sulfuric acid above 392° F. 4-Nitroaniline may also react with sodium hydroxide at 266° F. Under pressure, 4-Nitroaniline may produce an explosive compound. 4-Nitroaniline is incompatible with strong oxidizers and strong reducing agents. 4-Nitroaniline is capable of explosive decomposition with strong initiators. 4-Nitroaniline will attack some forms of plastics, rubber and coatings.
- HazardExplosion risk. Toxic when absorbed by skin. Methemoglobinemia, liver damage and eye irritant. Questionable carcinogen.
- Health HazardInhalation or ingestion causes headache, drowsiness, shortness of breath, nausea, methemoglobinemia, and unconsciousness; fingernails, lips, and ears become bluish; prolonged and excessive exposures may also cause liver damage. Contact with eyes causes irritation and possible corneal damage. Contact with skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion.
- Safety ProfilePoison by ingestion, intravenous, and intraperitoneal routes. Moderately toxic by intramuscular route. Mutation data reported. Acute symptoms of exposure are headache, nausea, vomiting, weakness and stupor, cyanosis and methemoglobinemia. Chronic exposure can cause liver damage. Experimental reproductive effects. Combustible when exposed to heat or flame. See NITRATES for explosion and disaster hazards. To fight fire, use water spray or mist, foam, dry chemical, CO2. Vigorous reaction with sulfuric acid above 200°C. Reaction with sodium hydroxide at 13O°C under pressure may produce the explosive sodium-4-nitrophenoxide. When heated to decomposition it emits toxic fumes of NOx. See also m- NITROANILINE, o-NITROANILINE, NITRO COMPOUNDS OF AROMATIC HYDROCARBONS, and ANILINE DYES.
- Potential Exposurep-Nitroaniline is used as an intermediate in the manufacture of dyes; antioxidants, pharmaceuticals, and pesticides.
- Carcinogenicityp-Nitroaniline has been tested in several strains of S. typhimurium. It was mutagenic in strain TA98 but not in strains TA97, TA100, TA1535, and TA1537, with and without S9. It caused gene mutation in mouse lymphoma cells and chromosomal aberrations in CHO cells in the presence of S9.
- Environmental FateBiological. A Pseudomonas sp. strain P6, isolated from a Matapeake silt loam, was grown using
a yeast extract. After 8 d, 4-nitroaniline degraded completely to carbon dioxide (Zeyer and
Kearney, 1983). In activated sludge inoculum, following a 20-d adaptation period, no degradation
was observed (Pitter, 1976).
Chemical/Physical: Spacek et al. (1995) investigated the photodegradation of 4-nitroaniline using titanium dioxide-UV light and Fenton’s reagent (hydrogen peroxide:substance – 10:1; Fe2+ 2.5 x 10-4 mol/L). Both experiments were conducted at 25 °C. The decomposition rate of 4-nitroaniline was very high by the photo-Fenton reaction in comparison to titanium dioxide-UV light (λ = 365 nm). Decomposition products identified in both reactions were nitrobenzene, pbenzoquinone, hydroquinone, oxalic acid, and resorcinol. Oxalic acid, hydroquinone, and pbenzoquinone were identified as intermediate products using HPLC.
At influent concentrations of 10, 1.0, 0.1, and 0.01 mg/L, the GAC adsorption capacities were 250, 140, 74, and 40 mg/g, respectively (Dobbs and Cohen, 1980).
- ShippingUN1661 Nitroanilines (m-, o-, p-), Hazard Class: 6.1; Labels: 6.1-Poisonous materials.
- Purification MethodsIt also crystallises from acetone. It is freed from o-and m-isomers by zone melting and sublimation. [Beilstein 12 IV 1613.]
- IncompatibilitiesA combustible liquid. A strong oxidizer. Incompatible with strong acids; sulfur, combustibles, organics, and other easily oxidizable materials. Will accelerate the burning of combustible materials. If large quantities are involved in a fire or the combustible material is finely divided, an explosion may result. Prolonged exposure to fire or heat may result in an explosion.
- Waste DisposalIncineration (982℃, 2.0 seconds minimum) with scrubbing for nitrogen oxides abatement. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≥100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
4-Nitroaniline Preparation Products And Raw materials
- Raw materialsAmmoniaWater4-Chloronitrobenzene2-BENZOYLACETANILIDE
- Preparation ProductsDisperse Orange 29AMIDO GREEN BLACK B6-AminoquinolineAcid Black 11,4-DINITROBENZENESIRIUS YELLOW GCAmsacrineDirect Black 192-BROMO-4-NITROANILINEdisodium 4-[[2,4-diamino-5-[(3-sulphonatophenyl)azo]phenyl]azo]-2-[[2,6-dihydroxy-3-[(4-nitrophenyl)azo]phenyl]azo]benzenesulphonate 3-CHLOROQUINOLIN-6-AMINEDisperse Red 74N-(4,6-DIMETHYLPYRIMIDIN-2-YL)BENZENE-1,4-DIAMINEDIRECT FAST BLACK G3-CHLORO-6-NITROQUINOLINEVACORDirect Green 89Disperse Orange 73Direct Green 26Acid Brown 75Catonic Dark Yellow 2RLFAST BLACK K SALT PRACTICAL GRADEDisperse Red 135Direct Grey DAcid Black 210N-BOC-L-leucylglycyl-arginine-p-nitroanilide hydrochloride2-[N-(2-acetoxyethyl)-4-chloro-2-nitro-5-[2-(propionamido)anilino]anilino]ethyl acetate DISPERSE RED 17Disperse Scarlet SE-RFast Black Base LSDISPERSE BLACK 14-Nitrophenyl isocyanateN-(4-NITROPHENYL)-4,6-DIMETHYL-2-PYRIMIDINAMINE[2-[ethyl[4-[(4-nitrophenyl)azo]phenyl]amino]ethyl]trimethylammonium chloride 3-[[2-(acetyloxy)ethyl][4-[(4-nitrophenyl)azo]phenyl]amino]propiononitrile CADIONDisperse Orange 25Disperse Blue 183methyl N-[4-[(2-chloro-4-nitrophenyl)azo]phenyl]-N-(2-cyanoethyl)-beta-alaninate Disperse Orange 37
- 3,4-Difluoronitrobenzene 4'-NITROACETANILIDE 2-Nitroaniline Nitroaniline 4-Nitrobenzonitrile 4-Nitrotoluene N-Methyl-4-nitroaniline 2-Methyl-4-nitroaniline 2,6-Dichloro-4-nitroaniline 1,3-Dinitrobenzene 4-Nitroaniline 6-Aminocaproic acid 3-Nitrochlorobenzene 4-Nitrobenzenesulfonyl chloride Nitrosobenzene Glycine 5-Nitroanthranilonitrile AMINO ACIDS