Bromnitromethan
255858_ALDRICH · EINECS 209-258-0 · bromonitro-methan · nitrobromomethane · BROMONITROMETHANE · Nitromethyl bromide · Methane, bromonitro- · Bromonitromethane, tech.
Identifikatoren & physikalische Daten
| CAS No. | 563-70-2 |
|---|---|
| Summenformel | Br.C.H2.N.O2 |
| Durchschnittliche Molmasse | 139,94 g/mol |
| Monoisotopische Masse | 138,9268904 g/mol |
| SMILES | O=[N+]([O-])CBr |
| InChIKey | DNPRVXJGNANVCZ-UHFFFAOYSA-N |
| PubChem CID | 68423 |
| ChEMBL | CHEMBL2335229 |
| EC No. | 209-258-0 |
| DTXSID | DTXSID7060338 |
| Lokaler Name | Bromnitromethan |
Chemische & physikalische Eigenschaften
| XLogP | 0,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 45,8 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 0 |
| Schwere Atome | 5 |
| Formalladung | 0 |
| Komplexität | 39,4 |
| SpringerMaterials Properties | Chemical shift |
| Dichte | 2.007 @25 °C2.007 g/mL at 25 °C (lit.) |
| Schmelzpunkt | -28 °C |
| Siedepunkt | 146-148 °C/750 mmHg (lit.) |
| Brechungsindex | 1.485-1.495 |
| Flammpunkt | 4°C |
| Lagerbedingungen | Storage temp. 2-8°C |
| Löslichkeit | Chloroform (Soluble), DMSO (Sparingly), Ethyl Acetate (Slightly), Methanol (Slig |
| pKa (Säurekonstante) | 7.22±0.29(Predicted) |
| Aggregatzustand | Liquid |
| Farbe | Clear yellow |
| Stabilität | Light Sensitive, Volatile |
| InChI | 1S/CH2BrNO2/c2-1-3(4)5/h1H2 |
| InChIKey | DNPRVXJGNANVCZ-UHFFFAOYSA-N |
| SMILES | [O-][N+](=O)CBr |
| CAS Datenbank | 563-70-2(CAS DataBase Reference) |
| EPA chemische Informationen | Methane, bromonitro- (563-70-2) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH272 (97.6%): May intensify fireoxidizer [Danger Oxidizing liquidsOxidizing solids]P210, P220, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 41 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.Methane, bromonitro-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Hazard Classes and Categories | Ox. Sol. 2 (97.6%) |
| Protective Action Criteria (PAC) | 0.40 [mg/m3]4.4 [mg/m3]26 [mg/m3] |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| UN-Transportnummer | 3098 |
| Zollcode | 29049095 |
| RTECS-Nr. | PA5360000 |
| R-Sätze (R) | 8-36/37/38-20/21/22 |
| Gefahrensymbole | Xn-O,Xi,O |
| Sicherheitshinweise (S) | 36/37/39-26-17-36 |
| Gefahrenklasse | 5.1Eye Irrit. 2Ox. Sol. 2Skin Irrit. 2STOT SE 3 |
| Verpackungsgruppe | III |
| Lagerklasse | 5.1B - Oxidizing hazardous materials |
Anwendungen & Verwendung
Verwenden
Bromonitromethane has received considerable attention as a one-carbon synthon for the synthesis of a variety of important organic intermediates. Bromonitromethane is a key starting material for the preparation of the broad-spectrum antibiotic trovafloxacin, which contains the interesting 3-azabicyclo[ 3.1.0]hexane ring system. it was used in the synthesis of 2-nitrobenzofuran and 2-nitro-2,3-dihydrobenzofuran-3-ols, nitrobenzothio-phenes, and nitrothiazoles, polyfunctionalized nitrocyclopropanes. It has also been utilized in the synthesis of 1-bromo-1-nitroalkan-2-ols and aryl nitromethanes. In addition, it could be used as a bromine donor.
Herstellung & Synthese
synthetische
Bromonitromethane is commercially available and can also be easily prepared according to the procedures reported by Fishwick et al. A typical procedure is as following: freshly distilled nitromethane was stirred at 0℃ and bromine was dropped in 5 seconds. The resulted bromonitromethane could be used without further purification.