| Identification | Back Directory | [Name]
5-Chlorothiophene-3-carbo... | [CAS]
36155-85-8 | [Synonyms]
5-Chlorothiophene-3-carbo...
5-chlorothiophene-3-carbaldehyde
5-Chlorothiophene-3-carboxaldehyde
3-Thiophenecarboxaldehyde, 5-chloro- | [Molecular Formula]
C5H3ClOS | [MDL Number]
MFCD17016115 | [MOL File]
36155-85-8.mol | [Molecular Weight]
146.59 |
| Chemical Properties | Back Directory | [Boiling point ]
208.8±20.0 °C(Predicted) | [density ]
1.429±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,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 |
| Hazard Information | Back Directory | [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 |
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