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| | 4-Bromothiophene-2-carboxaldehyde Basic information |
| | 4-Bromothiophene-2-carboxaldehyde Chemical Properties |
| Melting point | 44-46 °C (lit.) | | Boiling point | 114-115 °C/11 mmHg (lit.) | | density | 1.770 (estimate) | | Fp | >230 °F | | storage temp. | 2-8°C | | solubility | soluble in Methanol | | form | Powder or Granules | | color | White to beige | | Sensitive | Air Sensitive | | BRN | 108455 | | InChI | InChI=1S/C5H3BrOS/c6-4-1-5(2-7)8-3-4/h1-3H | | InChIKey | PDONIKHDXYHTLS-UHFFFAOYSA-N | | SMILES | C1(C=O)SC=C(Br)C=1 | | CAS DataBase Reference | 18791-75-8(CAS DataBase Reference) |
| | 4-Bromothiophene-2-carboxaldehyde Usage And Synthesis |
| Chemical Properties | white to light yellow crystal powder | | Uses |
4-Bromothiophene-2-carboxaldehyde has been used:
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as building block for the synthesis of tetrahydroisoquinolinones
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in the synthesis of 3-[(4-bromo-2-thienyl)methylenehydrazinocarbonyl]-1H-1,2,4-triazole
| | Application | 4-Bromothiophene-2-carboxaldehyde is an important and commonly used intermediate in medicinal chemistry.
| | Synthesis | General procedure: a THF solution of 1 M NaHMDS (8.8 mL, 8.8 mmol) was slowly added dropwise to the substrate (6.8 mmol) at 0°C. The reaction mixture was stirred for 30 min at 0 °C, then a solution of anhydrous THF (2 mL) with electrophilic reagent (8.3 mmol) was slowly added and stirring was continued for 3 h at 0 °C. Upon completion of the reaction, the reaction was quenched with saturated NH4Cl solution (5 mL) and diluted with hexane (20 mL). The organic layer was separated and washed with 15 wt% NaCl aqueous solution (10 mL) and subsequently concentrated to give the crude product. The product was purified by fast chromatography using a silica gel column pretreated with Et3N and 0.1% Et3N/4.9% EtOAc/95% hexane as eluent. | | Toxicity evaluation |
4-Bromothiophene-2-carboxaldehyde has acute oral toxicity and acute dermal toxicity, it causes skin corrosion/irritation and serious eye damage/eye irritation.
| | References | [1] Tetrahedron Letters, 2012, vol. 53, # 2, p. 166 - 169 |
| | 4-Bromothiophene-2-carboxaldehyde Preparation Products And Raw materials |
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