2-Nitroaniline CAS 88-74-4
Introduction：Basic information about 2-Nitroaniline CAS 88-74-4, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
2-Nitroaniline Basic information
| Product Name: | 2-Nitroaniline |
| Synonyms: | 1-amino-2-nitro-benzen;1-Nitro-2-aminobenzene;2-Aminonitrobenzene;2-nitro-benzenamin;2-Nitrobenzenamine;2-nitro-Benzenamine;2-Nitro-benzeneamine;2-Nitro-phenylamine |
| CAS: | 88-74-4 |
| MF: | C6H6N2O2 |
| MW: | 138.12 |
| EINECS: | 201-855-4 |
| Product Categories: | Chemical Class;N;NA - NI;N-OAlphabetic;Indicators for non-aqueous titrations;Indicators;Titration;Amines;C2 to C6Photonic and Optical Materials;Nitrogen Compounds;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Building Blocks;Chemical Synthesis;Materials Science;Nitrogen Compounds;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Organic and Printed Electronics;Organic Building Blocks;Photonic and Optical Materials;amine| nitro-compound;Alpha Sort;AromaticsVolatiles/ Semivolatiles;Intermediates;Pyridines;Anilines, Aromatic Amines and Nitro Compounds;Organics;Functional Materials;Organic Nonlinear Optical Materials;Intermediates of Dyes and Pigments;C6 |
| Mol File: | 88-74-4.mol |
2-Nitroaniline Chemical Properties
| Melting point | 70-73 °C (lit.) |
| Boiling point | 284 °C (lit.) |
| bulk density | 500kg/m3 |
| density | 1,255 g/cm3 |
| vapor pressure | 8.1 at 25 °C (Mabey et al., 1982) |
| refractive index | 1.6349 (estimate) |
| Fp | 168 °C |
| storage temp. | Store below +30°C. |
| solubility | methanol: 0.1 g/mL, clear |
| pka | -0.26(at 25℃) |
| form | Crystals or Flakes |
| Colour Index | 37025 |
| color | Orange to brown |
| PH | 6.1 (10g/l, H2O, 20℃)(slurry) |
| Water Solubility | 1.1 g/L (20 ºC) |
| Merck | 14,6582 |
| BRN | 509275 |
| Henry's Law Constant | 5.88 x 10-8 atm?m3/mol at 25 °C (thermodynamic method-GC/UV spectrophotometry, Altschuh et al., 1999) |
| Stability: | Stable. Incompatible with acids, acid chlorides, acid anhydrides, strong oxidizing agents, chloroformates, hexanitroethane. |
| InChI | 1S/C6H6N2O2/c7-5-3-1-2-4-6(5)8(9)10/h1-4H,7H2 |
| InChIKey | DPJCXCZTLWNFOH-UHFFFAOYSA-N |
| SMILES | Nc1ccccc1[N+]([O-])=O |
| LogP | 1.85 at 25℃ |
| CAS DataBase Reference | 88-74-4(CAS DataBase Reference) |
| NIST Chemistry Reference | o-Nitroaniline(88-74-4) |
| EPA Substance Registry System | o-Nitroaniline (88-74-4) |
Safety Information
| 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-16-7 |
| RIDADR | UN 1661 6.1/PG 2 |
| WGK Germany | 2 |
| RTECS | BY6650000 |
| F | 8 |
| Autoignition Temperature | 521 °C |
| TSCA | TSCA listed |
| HazardClass | 6.1 |
| PackingGroup | II |
| HS Code | 29214210 |
| Storage Class | 6.1A - Combustible acute toxic Cat. 1 and 2 very toxic hazardous materials |
| Hazard Classifications | Acute Tox. 3 Dermal Acute Tox. 3 Inhalation Acute Tox. 3 Oral Aquatic Chronic 3 STOT RE 2 |
| Hazardous Substances Data | 88-74-4(Hazardous Substances Data) |
| Toxicity | LD50 orally in Rabbit: 1600 mg/kg LD50 dermal Rabbit > 7940 mg/kg |
| Chemical Properties | orange solid |
| Uses | Dyestuff intermediate. |
| Uses | 2-Nitroaniline is the main precursor to?phenylenediamines, which are converted to?benzimidazoles, a family of?heterocycles?that are key components in pharmaceuticals. |
| Production Methods | 2-Chloronitrobenzene is heated with excess (10 mol/mol) strong aqueous ammonia in an autoclave. The temperature is gradually increased to 180 ℃ over 4 h and held there for 5 h more. The pressure builds up to around 4 MPa and is released to an ammonia recycle loop before the product is isolated by filtration and washing. The reaction is extremely exothermic, and too rapid heating or inadequate temperature control can result in a runaway reaction. Because of this hazard, I.G. Farbenindustrie developed a continuous amination unit for amination of chloronitrobenzenes; the process is summarized under 4-nitroaniline. |
| Synthesis Reference(s) | Journal of the American Chemical Society, 77, p. 5688, 1955 DOI: 10.1021/ja01626a066 Organic Syntheses, Coll. Vol. 1, p. 388, 1941 |
| General Description | Orange solid with a musty odor. Sinks and mixes slowly with water. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | 2-Nitroaniline may be sensitive to prolonged exposure to light. Mixtures of 2-Nitroaniline with magnesium are hypergolic on contact with nitric acid. 2-Nitroaniline forms extremely explosive addition compounds with hexanitroethane. 2-Nitroaniline has a vigorous reaction with sulfuric acid above 392° F. 2-Nitroaniline is incompatible with acids, acid chlorides, acid anhydrides, chloroformates and strong oxidizers. |
| Hazard | Explosion risk. Toxic when absorbed byskin. |
| Health Hazard | Inhalation or ingestion causes headache, nausea, methemo- globinemia, vomiting, weakness, and stupor; cyanosis caused by contact usually develops in 4-6 hrs.; prolonged and excessive exposure may also cause liver damage. Contact with eyes or skin causes irritation; continued exposure may cause same symptoms as inhalation or ingestion. |
| Fire Hazard | Special Hazards of Combustion Products: Toxic oxides of nitrogen may form in fire. |
| Safety Profile | A poison. Moderatelytoxic by ingestion. Mildly toxic by skincontact. Mutation data reported. Mixtureswith magnesium are hypergolic on contactwith nitric acid. Forms extremely explosiveaddltion compounds with hexanitroethane.Vigorous reaction with sulfuric acid above200°C. When heated to decomposition itemits toxic fumes of NOx. See also m-NITROANILINE, p-NITROANILINE,and ANILINE DYES. |
| Environmental fate | Biological. Under aerobic and anaerobic conditions using a sewage inoculum, 2-nitroanilinedegraded to 2-methylbenzimidazole and 2-nitroacetanilide (Hallas and Alexander, 1983). APseudomonas sp. strain P6, isolated from a Matapeake silt loam, did not grow on 2-nitroaniline asthe sole source of carbon. However, in the presence of 4-nitroaniline, approximately 50% of theapplied 2-nitroaniline metabolized to nonvolatile products which could not be identified by HPLC(Zeyer and Kearney, 1983). In activated sludge inoculum, following a 20-d adaptation period, nodegradation was observed (Pitter, 1976). Plant. 2-Nitroaniline was degraded by tomato cell suspension cultures (Lycopericonlycopersicum). Transformation products identified were 2-nitroanilino-β-D-glucopyranoside, β-(2-amino-3-nitrophenyl)glucopyranoside, and β-(4-amino-3-nitrophenyl)-glucopyranoside (Pogány etal., 1990). |
| Purification Methods | Crystallise the aniline from hot water (charcoal), then from aqueous 50% EtOH, or EtOH, and dry it in a vacuum desiccator. It has also been chromatographed on alumina, then recrystallised from *benzene. [Beilstein 12 IV 1563.] |
2-Nitroaniline Preparation Products And Raw materials
| Raw materials | Ammonia-->2-Nitrochlorobenzene |
| Preparation Products | o-Phenylenediamine-->2-Nitrochlorobenzene-->2-[3-(2H-Benzotriazol-2-yl)-4-hydroxyphenyl]ethyl methacrylate-->3,5-Dichloroaniline-->Albendazole-->Clemizole-->4-(Propylthio)benzene-1,2-diamine-->Bathophenanthroline-->Olaquindox-->2-Mercaptobenzimidazole-->2-Bromoaniline-->1,2-Dinitrobenzene-->Vat Red 14-->8-Nitroquinoline-->Pigment Yellow 5-->1-Bromo-2-nitrobenzene-->MEQUINDOX-->2-Nitro-4-thiocyanatoaniline-->Disperse Yellow 119-->2'-NITROACETANILIDE |
