5-Bromofuran-2-carbaldehyde
5-BROMOFURFURAL · 5-Bromo-2-furaldehyde acid · 5-BROMO-FURAN-2-CARBALDEHYDE · 5- Bromofural · 5-Bromo-2-furaL · 5-BROMO-2-FURFURAL · 5-Bromofuraldehyde · 5-bromo-2-furaldehye
Identifikatoren & physikalische Daten
| CAS No. | 1899-24-7 |
|---|---|
| Summenformel | C5H3BrO2 |
| Durchschnittliche Molmasse | 174,98 g/mol |
| Monoisotopische Masse | 173,93164 g/mol |
| SMILES | O=Cc1ccc(Br)o1 |
| InChIKey | WJTFHWXMITZNHS-UHFFFAOYSA-N |
| PubChem CID | 600328 |
| ChEMBL | CHEMBL2335228 |
| EC No. | 628-757-8 |
| DTXSID | DTXSID40344910 |
Chemische & physikalische Eigenschaften
| XLogP | 1,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 30,2 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 8 |
| Formalladung | 0 |
| Komplexität | 94 |
| Schmelzpunkt | 82-85 °C (lit.) |
| Siedepunkt | 112 °C/16 mmHg (lit.) |
| Dichte | 1.5940 (rough estimate) |
| Brechungsindex | 1.4450 (estimate) |
| Flammpunkt | 112°C/6mm |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Chloroform, Methanol |
| Aggregatzustand | Powder |
| Farbe | Slightly yellow |
| BRN | 108403 |
| Stabilität | Stable. Incompatible with strong oxidizing agents. |
| InChI | InChI=1S/C5H3BrO2/c6-5-2-1-4(3-7)8-5/h1-3H |
| InChIKey | WJTFHWXMITZNHS-UHFFFAOYSA-N |
| SMILES | O1C(Br)=CC=C1C=O |
| CAS Datenbank | 1899-24-7(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (95.7%): Harmful if swallowed [Warning Acute toxicity, oral]H312 (87.2%): Harmful in contact with skin [Warning Acute toxicity, dermal]H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]H332 (87.2%): Harmful if inhaled [Warning Acute toxicity, inhalation]H335 (97.9%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposureRespiratory tract irritation]P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, 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 47 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (95.7%)Acute Tox. 4 (87.2%)Skin Irrit. 2 (100%)Eye Irrit. 2 (100%)STOT SE 3 (97.9%) |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29130000 |
| R-Sätze (R) | 20/21/22-36/37/38 |
| Gefahrensymbole | Xn,Xi |
| hazard_note | Harmful |
| Sicherheitshinweise (S) | 26-36-36/37/39 |
| Gefahrenklasse | IRRITANTAcute Tox. 4 DermalAcute Tox. 4 InhalationAcute Tox. 4 OralEye Irrit. 2Skin Irrit. 2STOT SE 3 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Verwenden
5-Bromo-2-furaldehyde is used in the preparation of isoindolinones from furfural. Also used in the preparation of brominated nitrovinylfuran which displays antibacterial activity.
Herstellung & Synthese
synthetische
A three-necked 50 mL round bottom flask was charged with [bmim]Br3 (20 mmol) followed by dropwise addition of freshly distilled 2-furfural (20 mmol) over a period of 0.5 h and the reaction mixture was stirred for at 40 ℃ 2.5 h under nitrogen atmosphere. The mixture was extracted with petroleum ether (30 mL × 3), the organic layer was washed with water, dried (sodium sulfate) and concentrated. The crude product was purified by distillation and recrystallization with 10 % ethyl acetate-ether solution. 5-Bromo-2-furfural of yellowish crystal in 88 % yield was obtained. Mp. 82-85 ℃, 1H NMR (CDCl3), δ: 9.55 (s, 1H), 7.25 (s, 1H), 6.57 (s, 1H).