4'-Nitroacetanilid
P-NITROACETANILIDE · 4-NITROACETANILIDE · N-(4-Nitrophenyl)acetamide · n-(4-nitrophenyl)-acetamid · NSC 1315 · p-nitro-acetanilid · 4'-Nitroacetanilide · Acetanilide, p-nitro-
Identifikatoren & physikalische Daten
| CAS No. | 104-04-1 |
|---|---|
| Summenformel | C8H8N2O3 |
| Durchschnittliche Molmasse | 180,16 g/mol |
| Monoisotopische Masse | 180,05349212 g/mol |
| SMILES | CC(=O)Nc1ccc([N+](=O)[O-])cc1 |
| InChIKey | NQRLPDFELNCFHW-UHFFFAOYSA-N |
| PubChem CID | 7691 |
| ChEMBL | CHEMBL131469 |
| EC No. | 203-169-0 |
| DTXSID | DTXSID5059290 |
| Lokaler Name | 4'-Nitroacetanilid |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 74,9 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 13 |
| Formalladung | 0 |
| Komplexität | 204 |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | 1.66 |
| Schmelzpunkt | 213-215 °C(lit.) |
| Siedepunkt | 312.97°C (rough estimate) |
| Dichte | 1.340 |
| Brechungsindex | 1.6180 (estimate) |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | 2.2g/l2.2g/L(room temperature) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | 13.91±0.70(Predicted) |
| Farbe | Yellow to green-yellow or green-brown |
| Merck | 14,6581 |
| BRN | 2211962 |
| Stabilität | Stable. Combustible. Incompatible with strong oxidizing agents. |
| InChI | 1S/C8H8N2O3/c1-6(11)9-7-2-4-8(5-3-7)10(12)13/h2-5H,1H3,(H,9,11) |
| InChIKey | NQRLPDFELNCFHW-UHFFFAOYSA-N |
| SMILES | CC(=O)Nc1ccc(cc1)[N+]([O-])=O |
| CAS Datenbank | 104-04-1(CAS DataBase Reference) |
| EPA chemische Informationen | Acetamide, N-(4-nitrophenyl)- (104-04-1) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (97.8%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 46 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Acetamide, N-(4-nitrophenyl)-4'-Nitroacetanilide: Does not have an individual approval but may be used under an appropriate group standard |
| Hazard Classes and Categories | Skin Irrit. 2 (97.8%) |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29242990 |
| RTECS-Nr. | AE5075000 |
| R-Sätze (R) | 36/37/38 |
| Toxizität | rat,LDLo,intraperitoneal,500mg/kg (500mg/kg),National Academy of Sciences, National Research Council, Chemical-Biological Coordination Center, Review. Vol. 5, Pg. 10, 1953. |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Verwenden
Manufacture of nitraniline.
Herstellung & Synthese
synthetische
Preparation of 4'-Nitroacetanilide from acetanilide. Principle: Aromatic compounds can be conveniently nitrated by the use of the nitrating mixture, which is normally a mixture of concentrated nitric acid and concentrated sulphuric acid. The function of sulphuric acid is to convert nitric acid into a highly reactive, electrophilic, nitronium ion, NO2+, which is the effective nitrating agent. Nitration of activated aromatic compounds is carried out under milder condition whereas deactivated rings require drastic conditions. Activating groups are o, p-directing, while deactivating groups are m-directing for electrophilic substitution. Reaction: Procedure: Take 0.5 g acetanilide in 0.6 ml glacial acetic acid and add 1 ml conc. H2SO4 in a beaker. Cool the mixture in ice salt bath (5-10°C). To this add a mixture of 0.2 ml conc. H2SO4 and 0.25 ml conc. HNO3 dropwise. Maintain the temperature below 10°C during addition. After addition is over allow the mixture to attain room temperature and leave it for 30 minutes. Pour the mixture on to crushed ice (20 g) with stirring. Filter the separated product and wash with cold water. Dry the product, record the practical yield and re-crystallize it. Re-crystallization: Dissolve the crude product in minimum amount of ethyl alcohol in a beaker by heating on a water bath. Filter the hot solution and cool the filtrate. The crystals of the product separate out. Filter, dry and record the melting point and TLC (using toluene as solvent).