| 词条 | 4-Nitroaniline |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 477223057 | Name = 4-Nitroaniline | ImageFileL1 = p-Nitroanilin.svg | ImageSizeL1 = 65px | ImageAltL1 = Skeletal formula of p-nitroaniline | ImageFileR1 = 4-Nitroaniline-3D-balls.png | ImageSizeR1 = 110 | ImageAltR1 = Ball-and-stick model of the p-nitroaniline molecule | PIN = 4-Nitroaniline | SystematicName = 4-Nitrobenzenamine | OtherNames = p-Nitroaniline 1-Amino-4-nitrobenzene p-Nitrophenylamine |Section1={{Chembox Identifiers | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 1MRQ0QZG7G | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 13846959 | SMILES = c1cc(ccc1N)N(=O)=O | InChI = 1/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 | InChIKey = TYMLOMAKGOJONV-UHFFFAOYAW | StdInChI_Ref = {{stdinchicite|changed|chemspider}} | StdInChI = 1S/C6H6N2O2/c7-5-1-3-6(4-2-5)8(9)10/h1-4H,7H2 | StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} | StdInChIKey = TYMLOMAKGOJONV-UHFFFAOYSA-N | ChEBI_Ref = {{ebicite|changed|EBI}} | ChEBI = 17064 | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 14282 | CASNo_Ref = {{cascite|correct|CAS}} | CASNo = 100-01-6 |Section2={{Chembox Properties | Formula = C6H6N2O2 | MolarMass = 138.12 g/mol | Appearance = yellow or brown powder | Odor = faint, ammonia-like | Density = 1.437 g/ml, solid | Solubility = 0.8 mg/ml at 18.5 °C (IPCS) | MeltingPtC = 146 to 149 | MeltingPt_notes = (lit.) | BoilingPtC = 332 | BoilingPt_notes = | VaporPressure = 0.00002 mmHg (20°C)[1] | MagSus = -66.43·10−6 cm3/mol |Section7={{Chembox Hazards | ExternalSDS = JT Baker | MainHazards = Toxic | EUClass = {{hazchem T}} {{hazchem N}} | NFPA-H = 2 | NFPA-F = 1 | NFPA-R = 0 | NFPA-S = | RPhrases = {{R23/24/25}} {{R33}} {{R52/53}} | SPhrases = {{S28}} {{S36/37}} {{S45}} {{S61}} | FlashPtC = 199 | PEL = TWA 6 mg/m3 (1 ppm) [skin][1] | IDLH = 300 mg/m3[1] | REL = TWA 3 mg/m3 [skin][1] | LD50 = 3249 mg/kg (rat, oral) 750 mg/kg (rat, oral) 450 mg/kg (guinea pig, oral) 810 mg/kg (mouse, oral)[2] |Section8={{Chembox Related | OtherCompounds = 2-Nitroaniline, 3-Nitroaniline }} 4-Nitroaniline, p-nitroaniline or 1-amino-4-nitrobenzene is an organic compound with the formula C6H6N2O2. It is an organic chemical compound, consisting of a benzene ring in which an amino group is para to a nitro group. This chemical is commonly used as an intermediate in the synthesis of dyes, antioxidants, pharmaceuticals, gasoline, gum inhibitors, poultry medicines, and as a corrosion inhibitor. SynthesisIt is produced industrially via the amination of 4-nitrochlorobenzene:[3] ClC6H4NO2 + 2 NH3 → H2NC6H4NO2 + NH4Cl Below is a laboratory synthesis of 4-nitroaniline from aniline. The key step in this reaction sequence is an electrophilic aromatic substitution to install the nitro group para to the amino group. The amino group can be easily protonated and become a meta director. Therefore, a protection of the acetyl group is required. After this reaction, a separation must be performed to remove 2-nitroaniline, which is also formed in a small amount during the reaction.[4] Applications4-Nitroaniline is mainly consumed industrially as a precursor to p-phenylenediamine, an important dye component. The reduction is effected using iron metal and by catalytic hydrogenation.[3] It is a starting material for the synthesis of Para Red, the first azo dye:[5] When heated with sulfuric acid, it polymerizes explosively into a rigid foam.[6] Laboratory useNitroaniline is a solvatochromic dye used for determining Kamlet-Taft solvent parameters. The position of its UV-visual peak changes with the balance of hydrogen bonding acceptors and donors in the solvent.{{Citation needed|date=June 2015}} ToxicityThe compound is toxic by way of inhalation, ingestion, and absorption, and should be handled with care. Its {{LD50}} in rats is 750 mg/kg when administered orally. 4-Nitroaniline is particularly harmful to all aquatic organisms, and can cause long-term damage to the environment if released as a pollutant.{{Citation needed|date=June 2015}} See also
References1. ^1 2 3 {{PGCH|0449}} 2. ^{{IDLH|100016|p-Nitroaniline}} 3. ^1 {{cite journal|author=Gerald Booth|title=Nitro Compounds, Aromatic|encyclopedia=Ullmann's Encyclopedia of Industrial Chemistry|year=2007|publisher=Wiley-VCH|location=Weinheim|doi=10.1002/14356007.a17_411}} 4. ^Mohrig, J.R.; Morrill, T.C.; Hammond, C.N.; Neckers, D.C. "Synthesis 5: Synthesis of the Dye Para Red from Aniline." Experimental Organic Chemistry. Freeman: New York, NY, 1997; pp 456-467. 5. ^{{cite book |last = Williamson |first = Kenneth L. |title = Macroscale and Microscale Organic Experiments, Fourth Edition |publisher = Houghton-Mifflin |year = 2002 |isbn = 0-618-19702-8}} 6. ^{{cite journal|title=Studies on nitroaniline–sulfuric acid compositions: Aphrogenic pyrostats|doi=10.1002/app.1970.070140813}} External links
5 : Anilines|Dyes|Hazardous air pollutants|IARC Group 3 carcinogens|Nitrobenzenes |
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