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| | 5-Bromothiophene-2-carbaldehyde Basic information |
| | 5-Bromothiophene-2-carbaldehyde Chemical Properties |
| Melting point | 55°C | | Boiling point | 105-107 °C11 mm Hg(lit.) | | density | 1.607 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.637(lit.) | | Fp | 210 °F | | storage temp. | 2-8°C | | solubility | Soluble in chloroform and methanol. | | form | Liquid After Melting | | color | Clear yellow to brown | | Sensitive | Air Sensitive | | BRN | 108404 | | InChI | 1S/C5H3BrOS/c6-5-2-1-4(3-7)8-5/h1-3H | | InChIKey | GFBVUFQNHLUCPX-UHFFFAOYSA-N | | SMILES | [H]C(=O)c1ccc(Br)s1 | | LogP | 2.566 (est) | | CAS DataBase Reference | 4701-17-1(CAS DataBase Reference) | | NIST Chemistry Reference | 5-Bromo-2-thiophenecarboxaldehyde(4701-17-1) |
| | 5-Bromothiophene-2-carbaldehyde Usage And Synthesis |
| Chemical Properties | clear yellow to brown liquid after melting | | Uses | 5-Bromo-2-thiophenecarboxaldehyde was used to prepare 5-[18F]fluoro-2-2-thiophene carboxaldehyde. Also is used in biological studies as anti-inflammatory and anti-tumor activity of the marine mangrove Rhizophora apiculata. | | Synthesis Reference(s) | Journal of the American Chemical Society, 72, p. 1422, 1950 DOI: 10.1021/ja01159a527 | | Synthesis | 2.1.1 Synthesis of 5-bromo-2-thiophenecarboxaldehyde
Under nitrogen protection, 2-thiophenecarboxaldehyde (6.0 g, 53.5 mmol) was dissolved in anhydrous chloroform (125 mL). Subsequently, N-bromosuccinimide (10.4 g, 58.9 mmol) was slowly added and the reaction mixture was stirred for 12 h at room temperature. After completion of the reaction, the mixture was extracted with chloroform (3 × 50 mL), and the organic phases were combined and washed with deionized water (2 × 50 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. The crude product was purified by silica gel column chromatography using chloroform as eluent to afford 5-bromo-2-thiophenecarboxaldehyde as a colorless oil (10.0 g, 98% yield).
1H NMR (400 MHz, CDCl3): δ 7.20 (d, 1H, J = 4.0 Hz), 7.53 (d, 1H, J = 8.0 Hz), 9.79 (s, 1H). | | References | [1] Physica B: Condensed Matter, 2017, vol. 519, p. 53 - 58
[2] Tetrahedron, 2007, vol. 63, # 37, p. 9188 - 9194
[3] Tetrahedron Letters, 2005, vol. 46, # 12, p. 1989 - 1992
[4] Patent: WO2018/67786, 2018, A1. Location in patent: Page/Page column 134; 135
[5] Journal of the Chemical Society, 1958, p. 1721 |
| | 5-Bromothiophene-2-carbaldehyde Preparation Products And Raw materials |
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