|
|
| | 5-Bromo-2-furaldehyde Basic information |
| | 5-Bromo-2-furaldehyde Chemical Properties |
| Melting point | 82-85 °C (lit.) | | Boiling point | 112 °C/16 mmHg (lit.) | | density | 1.5940 (rough estimate) | | refractive index | 1.4450 (estimate) | | Fp | 112°C/6mm | | storage temp. | 2-8°C | | solubility | Chloroform, Methanol | | form | Powder | | color | Slightly yellow | | Sensitive | Air Sensitive | | BRN | 108403 | | Stability: | 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 DataBase Reference | 1899-24-7(CAS DataBase Reference) |
| Hazard Codes | Xn,Xi | | Risk Statements | 20/21/22-36/37/38 | | Safety Statements | 26-36-36/37/39 | | WGK Germany | 3 | | Hazard Note | Harmful | | HazardClass | IRRITANT | | HS Code | 29130000 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | 5-Bromo-2-furaldehyde Usage And Synthesis |
| Chemical Properties | solid | | Physical properties | 5-Bromo-2-furfuraldehyde is a light yellow powder, soluble in carbon dichloride , carbon tetrachloride, ether and other organic solvents. | | Uses | 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. | | Uses | 5-Bromo-2-furaldehyde may be employed for the following syntheses:
- 5-substituted 2-furaldehydes
- anilines, through a novel one-pot, two-step amination/Diels-Alder procedure
- 5-(5′,8′-dimethyl-9′-tert-butoxycarbonyl-9′H-carbazol-3′-yl)-furan-2-carbaldehyde
- 5-(6-hydroxyhexyl)-2-furaldehyde
- 5-methylsulfonyl-2-furaldehyde
- 5-phenylsulfonyl-2-furaldehyde
- 5-(4-acetamidobenzylsulfonyl)-2-furaldehyde
- 5-iodo-2-furaldehyde
| | Preparation | 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). |
| | 5-Bromo-2-furaldehyde Preparation Products And Raw materials |
|