Methyl 2,2-dithienylglycolate Chemical Properties

Melting point:

93-95°C

Boiling point:

406.5±40.0 °C(Predicted)

Density 

1.392±0.06 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

DMSO (Slightly), Methanol (Slightly, Heated)

form 

Solid

pka

10.43±0.29(Predicted)

color 

White to Light Brown

InChI

InChI=1S/C11H10O3S2/c1-14-10(12)11(13,8-4-2-6-15-8)9-5-3-7-16-9/h2-7,13H,1H3

InChIKey

SYHWYWHVEQQDMO-UHFFFAOYSA-N

SMILES

C(C1SC=CC=1)(C1SC=CC=1)(O)C(=O)OC

CAS DataBase Reference

26447-85-8(CAS DataBase Reference)

Safety Information

HS Code 

2934999090

Methyl 2,2-dithienylglycolate Usage And Synthesis

Chemical Properties

White Solid

Uses

Methyl Di(2-thienylglycolate) (Tiotropium EP Impurity E) is an intermediate in the production of Tiotropium Bromide, a long-acting bronchodilator.

Synthesis

Under nitrogen protection, 2-bromothiophene (9.68 mL, 0.1 mol) was slowly added dropwise to a stirred mixture of magnesium scrapings (2.7 g, 0.11 mol) and ether (100 mL), keeping the reaction temperature at 0 °C. Subsequently, the reaction mixture was warmed up to 35 °C with continuous stirring. Next, a solution of dimethyl oxalate (5.9 g, 0.05 mol) in ether (150 mL) was slowly added dropwise over a period of 3 hours. After the dropwise addition was completed, the reaction mixture was heated to reflux (45 °C) and maintained for 45 minutes. Upon completion of the reaction, the mixture was cooled to room temperature and 1.25 M sulfuric acid (150 mL) was added. After stirring for 1 h at room temperature, the organic layer was separated and washed sequentially with dilute aqueous sodium bicarbonate (100 mL) and water (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting solid residue was recrystallized with carbon tetrachloride (1 g / 3 mL) to afford methyl 2,2-dithienyl ethanoate (7.68 g, 30 mmol, 60% yield).

References

[1] Patent: US2004/242622, 2004, A1. Location in patent: Page 29

Methyl 2,2-dithienylglycolate(26447-85-8)Related Product Information

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