2-Nitrobenzaldehyd
O-NITROBENZALDEHYDE · 2-nitro-benzaldehyd · 2-NBA · 2-Nitrobenzenecarboxaldehyde · 2-Nitobenzaldehyde · 1-ForMyl-2-nitrobenzene · NSC 5713 · AKOS 93864
Identifikatoren & physikalische Daten
| CAS No. | 552-89-6 |
|---|---|
| Summenformel | C7H5NO3 |
| Durchschnittliche Molmasse | 151,12 g/mol |
| Monoisotopische Masse | 151,02694302 g/mol |
| SMILES | O=Cc1ccccc1[N+](=O)[O-] |
| InChIKey | CMWKITSNTDAEDT-UHFFFAOYSA-N |
| PubChem CID | 11101 |
| ChEMBL | CHEMBL166559 |
| ChEBI | CHEBI:66927 |
| EC No. | 209-025-3 |
| DTXSID | DTXSID0022060 |
| Lokaler Name | 2-Nitrobenzaldehyd |
Chemische & physikalische Eigenschaften
| XLogP | 1,7 |
|---|---|
| Polarare Oberfläche (TPSA) | 62,9 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 11 |
| Formalladung | 0 |
| Komplexität | 164 |
| Stoffklassen | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| SpringerMaterials Properties | 13C nuclear magnetic resonance spectrum |
| LogP (Verteilungskoeffizient) | 1.74 |
| Physical Description | Partially soluble in water (2.32 g/L at 25 deg C)[ChemIDplus] Yellow crystalline powder[MSDSonline] |
| Ionization Efficiency | Positive0.782.7Agilent XCTElectrospray ionizationformic acid (5.3nM) |
| Schmelzpunkt | 42-44 °C(lit.) |
| Siedepunkt | 153 °C23 mm Hg(lit.) |
| Dichte | 1,284 g/cm3 |
| Dampfdichte | 5.2 (vs air) |
| Brechungsindex | 1.5800 (estimate) |
| Flammpunkt | >230 °F |
| Lagerbedingungen | Store below +30°C. |
| Löslichkeit | Chloroform (Slightly), Ethyl Acetate (Slightly)Insoluble in water. |
| Aggregatzustand | Crystalline Powder, Needles and/or Chunks |
| Farbe | Yellow |
| Merck | 14,6586 |
| BRN | 742624 |
| InChI | 1S/C7H5NO3/c9-5-6-3-1-2-4-7(6)8(10)11/h1-5H |
| InChIKey | CMWKITSNTDAEDT-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)c1ccccc1C=O |
| LogP (Verteilungskoeffizient) | 1.74 at 25℃ |
| CAS Datenbank | 552-89-6(CAS DataBase Reference) |
| NIST chemische Informationen | Benzaldehyde, 2-nitro-(552-89-6) |
| EPA chemische Informationen | Benzaldehyde, 2-nitro- (552-89-6) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (97.5%): Harmful if swallowed [Warning Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 120 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzaldehyde, 2-nitro-Status: Active Update: 06-09-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/11680Restricted substance: o-NitrobenzaldehydeBenzaldehyde, 2-nitro-: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - Benzaldehyde, 2-nitro-: Human health tier I assessment |
| Gefahrenübersicht | An irritant[MSDSonline] See 3-Nitrobenzaldehyde. |
| Hazard Classes and Categories | Acute Tox. 4 (97.5%) |
| F | 8 |
| Wassergefährdungsklasse (WGK) | 2 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29130000 |
| RTECS-Nr. | CU7300000 |
| R-Sätze (R) | 22-36/37/38-68 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Irritant |
| Sicherheitshinweise (S) | 26-24/25-36/37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
| Gefahrenklasse | Acute Tox. 4 OralAquatic Chronic 3Eye Irrit. 2Skin Irrit. 2STOT SE 3 |
Anwendungen & Verwendung
Beschreibung
2-Nitrobenzaldehyde (2-NBA) is a multifunctional compound used in dyes, pharmaceuticals, food, and organic synthesis. Due to its distinctive yellow crystalline appearance, 2-NBA is used as an intermediate in the synthesis of indigo dyes. It is also used in the synthesis of 2-Nitrobenzyl-chitosan and nifedipine. Furthermore, 2-NBA can be used as a preservative in meat products, for the preservation of meat and food (preventing light damage), and has applications in the packaging industry.
Verwenden
2-Nitrobenzaldehyde is a benzaldhyde with a nitro group substituted in the ortho position. 2-Nitrobenzaldehyde is used in the preparation of dyes and colorants such as Indigo carmine. 2-Nitrobenzaldehyde gas been shown to be a useful photoremovable protecting group as well as in the preparation of more effective ones such as o-Nitrophenylethylene glycol.
Herstellung & Synthese
synthetische
2-Nitrobenzaldehyde is synthesized from 2-Nitrotoluene by nitration and oxidation.Synthesis of 2-Nitrobenzaldehyde from 2-Nitrotoluene