3-Nitroaniline CAS 99-09-2
Introduction：Basic information about 3-Nitroaniline CAS 99-09-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
3-Nitroaniline Basic information
| Product Name: | 3-Nitroaniline |
| Synonyms: | 3-NitroaniL;M-NITRANILINE;M-NITROANILINE;fastorangersalt;Hiltonil Fast Orange R Base;hiltonilfastorangerbase;m-Nitroaminobenzene;m-nitro-anilin |
| CAS: | 99-09-2 |
| MF: | C6H6N2O2 |
| MW: | 138.12 |
| EINECS: | 202-729-1 |
| Product Categories: | Dyestuff Intermediates;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;Photonic and Optical Materials;Building Blocks;C6;C2 to C6Photonic and Optical Materials;Nitro Compounds;N-OAlphabetic;Chemical Synthesis;Materials Science;Nitrogen Compounds;Organic and Printed Electronics;Organic Building Blocks;Intermediates of Dyes and Pigments;Anilines, Aromatic Amines and Nitro Compounds;Organics;Amines;Nitrogen Compounds;NLO Chromophores and Intermediates;Non-Linear Optical (NLO) Materials;C2 to C6;Alpha Sort;Analytical Standards;AromaticsChemical Class;AromaticsVolatiles/ Semivolatiles;Chemical Class;N;NA - NIAnalytical Standards;NA - NI;Functional Materials;Organic Nonlinear Optical Materials |
| Mol File: | 99-09-2.mol |
3-Nitroaniline Chemical Properties
| Melting point | 111-114 °C (lit.) |
| Boiling point | 306 °C |
| density | 0,901 g/cm3 |
| vapor pressure | 1 mm Hg ( 119 °C) |
| refractive index | 1.6396 (estimate) |
| Fp | 196 °C |
| storage temp. | Store below +30°C. |
| solubility | 1.25g/l |
| Colour Index | 37030 |
| form | Crystals, Crystalline Powder and/or Chunks |
| pka | 2.466(at 25℃) |
| color | Yellow to ochre-yellow to orange |
| Specific Gravity | 0.901 |
| Water Solubility | 1.25 g/L |
| Merck | 14,6581 |
| BRN | 636962 |
| Henry's Law Constant | 1.93 x 10-5 atm?m3/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) |
| NIST Chemistry Reference | m-Nitroaniline(99-09-2) |
| EPA Substance Registry System | m-Nitroaniline (99-09-2) |
Safety Information
| Hazard Codes | T |
| Risk Statements | 23/24/25-33-52/53 |
| Safety Statements | 28-36/37-45-61-28A |
| RIDADR | UN 1661 6.1/PG 2 |
| WGK Germany | 2 |
| RTECS | BY6825000 |
| F | 8 |
| Autoignition Temperature | 521℃ |
| 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 Oral |
| 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). |
| Chemical Properties | 3-Nitroaniline is a ochre-yellow to orange crystalline powder, crystallizes as yellow needles from water. It is moderately soluble in organic solvents and sparingly soluble in water (0.11 %). |
| Physical properties | Yellow, rhombic crystals or powder. Finely dispersered particles form explosive mixtures.Combustible. |
| 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. |
| Production Methods | 1,3-Dinitrobenzene is added to warm water containing magnesium sulfate. An aqueous solution of sodium hydrogen sulfide (6 molar equivalents) is added gradually to the vigorously stirred emulsion, and reduction is completed by heating to 90 ℃. The 3-nitroaniline produced solidifies on cooling and is separated by filtration. |
| Preparation | M-nitroaniline partial reduction. |
| Synthesis Reference(s) | The Journal of Organic Chemistry, 45, p. 4992, 1980 DOI: 10.1021/jo01312a039 Tetrahedron Letters, 30, p. 251, 1989 DOI: 10.1016/S0040-4039(00)95173-6 Chemical and Pharmaceutical Bulletin, 34, p. 2013, 1986 DOI: 10.1248/cpb.34.2013 |
| General Description | Yellow needles or yellow powder. |
| Air & Water Reactions | Insoluble in water. |
| Reactivity Profile | Thermal stability of 3-Nitroaniline is reduced by various impurities. 3-Nitroaniline may be sensitive to prolonged exposure to light. 3-Nitroaniline may react explosively with ethylene oxide at 266° F. 3-Nitroaniline is incompatible with acids (nitric, sulfuric), acid chlorides, acid anhydrides, chloroformates and strong oxidizing agents. . Unstable when heated. |
| Hazard | Moderate fire risk. Toxic when absorbed byskin. |
| Fire Hazard | Flash point data for 3-Nitroaniline are not available; however, 3-Nitroaniline is probably combustible. |
| Synthesis | 1,3-Dinitrobenzene is added towarmwater containing magnesium sulfate. An aqueous solution of sodium hydrogen sulfide (6molar equivalents) is added gradually to the vigorously stirred emulsion, and reduction is completed by heating to 90℃. The 3-nitroaniline produced solidifies on cooling and is separated by filtration. |
| Environmental fate | Biological. A bacterial culture isolated from the Oconee River in North Georgia degraded 3-nitroaniline to the intermediate 4-nitrocatechol (Paris and Wolfe, 1987). A Pseudomonas sp. strainP6, isolated from a Matapeake silt loam, did not grow on 3-nitroaniline as the sole source ofcarbon. However, in the presence of 4-nitroaniline, all of the applied 3-nitroaniline metabolizedcompletely to carbon dioxide (Zeyer and Kearney, 1983). In the presence of suspended naturalpopulations from unpolluted aquatic systems, the second-order microbial transformation rateconstant determined in the laboratory was reported to be 4.6 ± 0.1 x 10-13 L/organism?h (Steen,1991). In activated sludge inoculum, following a 20-d adaptation period, no degradation was observed(Pitter, 1976). Chemical/Physical. Reacts with acids forming water soluble salts. |
| Purification Methods | Purify it as for o-nitroaniline. Warning: it is absorbed through the skin. [Beilstein 12 IV 1589.] |
3-Nitroaniline Preparation Products And Raw materials
| Raw materials | Sulfuric acid-->Nitric acid-->Sulfur-->Sodium sulfite-->Sodium sulfide-->Nitrobenzene-->1,3-Dinitrobenzene-->SODIUM TETRASULFIDE-->CALCIUM SULFIDE-->3-Bromonitrobenzene-->3-nitrophenyl azide-->3-Aminobenzeneboronic acid-->3-Nitroaniline |
| Preparation Products | 3-Bromoaniline-->3-Fluoroaniline-->1,3-Difluorobenzene-->1-(3-NITROPHENYL)-PIPERAZINE-->N-(3-Aminophenyl)methanesulfamide-->5-Aminoquinoline-->N1-(3-Aminophenyl)acetamide-->3-Hydroxy-N-(3-nitrophenyl)-2-naphthalenecarboxamide-->3-Nitrophenol-->Disperse Red 74-->4-hydroxy-1-methyl-3-[(3-nitrophenyl)azo]-2-quinolone-->Mordant Yellow 1-->3-NITROBIPHENYL-->Disperse Red S-2GFL-->3'-NITROACETANILIDE-->1,7-PHENANTHROLINE-->2,7-Naphthalenedisulfonicacid, 3-hydroxy-4-[2-(3-nitrophenyl)diazenyl]-, sodium salt (1:2)-->DISPERSE YELLOW 5 |
