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

Safety Information

HS Code 

2934999090

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-(36155-85-8)Related Product Information

• Benzaldehyde
• 5-CHLOROTHIOPHENE-3-CARBOXYLIC ACID
• o-Phthalaldehyde
• CALCIUM ALUMINATE