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| | 2-Acetyl-5-bromothiophene Basic information |
| | 2-Acetyl-5-bromothiophene Chemical Properties |
| Melting point | 94-96 °C (lit.) | | Boiling point | 103 °C/4 mmHg (lit.) | | density | 1.649 (estimate) | | Fp | 103°C/4mm | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | solubility | soluble in Methanol | | form | Crystalline Flakes or Powder | | color | Yellow | | Sensitive | Light Sensitive | | BRN | 113949 | | InChI | InChI=1S/C6H5BrOS/c1-4(8)5-2-3-6(7)9-5/h2-3H,1H3 | | InChIKey | IGBZCOWXSCWSHO-UHFFFAOYSA-N | | SMILES | C(=O)(C1SC(Br)=CC=1)C | | CAS DataBase Reference | 5370-25-2(CAS DataBase Reference) | | NIST Chemistry Reference | 2-Acetyl-5-bromothiophene(5370-25-2) |
| Hazard Codes | Xn | | Risk Statements | 36/37/38-20/21/22 | | Safety Statements | 36/37/39-26-22 | | RIDADR | UN2811 | | WGK Germany | 3 | | HazardClass | LIGHT SENSITIVE | | HS Code | 29339900 | | Storage Class | 11 - Combustible Solids |
| | 2-Acetyl-5-bromothiophene Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses | 2-Acetyl-5-bromothiophene was used as a starting reagent in the synthesis of bithiophene bis-imidazo[1,2-a]pyridine derivatives. It was also used in the preparation of phosphorus-containing fused bicyclic 5,6-membered compounds. | | Synthesis Reference(s) | Journal of Heterocyclic Chemistry, 18, p. 1345, 1981 DOI: 10.1002/jhet.5570180714
Synthetic Communications, 11, p. 29, 1981 DOI: 10.1080/00397918108064279 | | Synthesis | The general procedure for the synthesis of 2-acetyl-5-bromothiophene from 2-acetylthiophene was as follows: 2-acetylthiophene (1.08 mL, 10 mmol), N-bromosuccinimide (NBS) (1.78 g, 30 mmol), and acetic anhydride (3.78 mL, 40 mmol) were added sequentially to a dry, 25 mL round-bottomed flask, which was equipped with a protective tube. Acetic acid (0.40 mL) was subsequently added to the mixture. The reaction mixture was stirred at 50 °C for 1 h protected from light and the color of the solution was observed to change from colorless to light yellow. Upon completion of the reaction, the mixture was cooled to room temperature and poured into 100 mL of water with continuous stirring until the acetic anhydride was completely hydrolyzed. At this point, 2-acetyl-5-bromothiophene precipitated as white crystals. The product was collected by filtration and washed in batches with 50 mL of water to give a final yield of 82%. The melting point of the product was 92-94 °C (acetone).1H NMR (300 MHz, CDCl3) data were as follows: δ 7.40 (d, J=3.9 Hz, 1H), 7.08 (d, J=3.9 Hz, 1H), 2.48 (s, 3H). | | References | [1] Tetrahedron Letters, 2010, vol. 51, # 1, p. 205 - 208
[2] Journal of Organic Chemistry, 2009, vol. 74, # 23, p. 9180 - 9187
[3] Tetrahedron Letters, 2014, vol. 55, # 5, p. 996 - 1001
[4] Organic Letters, 2013, vol. 15, # 9, p. 2108 - 2111 |
| | 2-Acetyl-5-bromothiophene Preparation Products And Raw materials |
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