|
|
| | 3-Thiophenecarboxaldehyde, 5-chloro- Basic information |
| | 3-Thiophenecarboxaldehyde, 5-chloro- Chemical Properties |
| Boiling point | 208.8±20.0 °C(Predicted) | | density | 1.429±0.06 g/cm3(Predicted) | | storage temp. | under inert gas (nitrogen or Argon) at 2–8 °C | | Appearance | light yellow liquid | | InChI | InChI=1S/C5H3ClOS/c6-5-1-4(2-7)3-8-5/h1-3H | | InChIKey | BGOGYRKWKJGOHZ-UHFFFAOYSA-N | | SMILES | C1SC(Cl)=CC=1C=O |
| | 3-Thiophenecarboxaldehyde, 5-chloro- Usage And Synthesis |
| Uses | 5-Chloro-3-thiophenecarboxaldehyde is a useful reagent in the preparation of 2,4-Diaminopyrimidine derivatives as potent growth hormone secretagogue receptor antagonists. | | Synthesis | General procedure for the synthesis of 5-chlorothiophene-3-carbaldehyde from 3-thiophenecarboxaldehyde: The reaction was carried out to a solution of thiophene-3-carbaldehyde (20.0 g, 178.3 mmol) and N-chlorosuccinimide (23.8 g, 178.3 mmol) in acetic acid (180 mL) with stirring for 4 hours at 110 °C. After completion of the reaction, the reaction solution was cooled to room temperature, then diluted with ethyl acetate (120 mL), washed sequentially with water (100 mL x 3), saturated sodium bicarbonate solution (50 mL x 2) and brine, and the organic phase was dried with anhydrous sodium sulfate. After concentration under reduced pressure, 5-chlorothiophene-3-carbaldehyde (8.0 g, 54.6 mmol, 31% yield) was obtained as a yellow solid, which could be used for subsequent reactions without further purification. | | References | [1] Patent: WO2015/140133, 2015, A1. Location in patent: Page/Page column 110
[2] Journal of Medicinal Chemistry, 2006, vol. 49, # 8, p. 2568 - 2578
[3] Patent: WO2015/142903, 2015, A2. Location in patent: Page/Page column 98 |
| | 3-Thiophenecarboxaldehyde, 5-chloro- Preparation Products And Raw materials |
|