Ethyl 5-bromothiophene-2-carboxylate Chemical Properties

Boiling point:

94-96°C/4mm

Density 

1.572±0.06 g/cm3(Predicted)

refractive index 

1.5600 to 1.5640

Flash point:

94-96°C/4mm

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

clear liquid

color 

Light orange to Yellow to Green

Water Solubility 

Slightly soluble in water

λmax

277nm(Hexane)(lit.)

InChI

InChI=1S/C7H7BrO2S/c1-2-10-7(9)5-3-4-6(8)11-5/h3-4H,2H2,1H3

InChIKey

PZNHMXAOMDQLLE-UHFFFAOYSA-N

SMILES

C1(C(OCC)=O)SC(Br)=CC=1

Safety Information

HS Code 

29349990

Ethyl 5-bromothiophene-2-carboxylate Usage And Synthesis

Chemical Properties

Colourless to light yellow liquid

Uses

Ethyl 5-bromothiophene-2-carboxylate is used as an intermediate in organic syntheses

Synthesis

GENERAL STEPS: To a solution of commercially available 5-bromothiophene-2-carboxylic acid (10 g, 0.048 mol) and cesium carbonate (31.6 g, 0.096 mol) in N,N-dimethylformamide (100 mL) was slowly added ethyl iodide (11.3 g, 0.072 mol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the reaction was quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product. The crude product was purified by silica gel column chromatography to afford pure ethyl 5-bromothiophene-2-carboxylate (9 g, 80% yield) as a light yellow oil.ESI-MS m/z: 234.1 [M + H]+ (calculated value: C7H7BrO2S).1H NMR (CDCl3, 400 MHz): δ 7.54-7.53 (d, J = 4 Hz, 1H, Harom), 7.07-7.53 (d, J = 4 Hz, 1H, Harom). Harom), 7.07-7.06 (d, J = 4 Hz, 1H, Harom), 4.35-4.30 (m, 2H, O-CH2-CH3), 1.38-1.34 (m, 3H, O-CH2-CH3).

References

[1] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 506 - 524

Ethyl 5-bromothiophene-2-carboxylate(5751-83-7)Related Product Information

• Urethane
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• ISOXADIFEN-ETHYL
• Ethyl propiolate
• Tris(trimethylsilyl)phosphate
• Triethyl orthoformate
• Ethylparaben
• RESMETHRIN
• Ethyl cyanoacetate
• Ethyl cyanoformate
• Ethyl acrylate
• Methyl acrylate
• Ethyl formate
• Ethanol
• Ethyl acetate
• 5-Bromothiazole
• 5-Bromothiophene-2-carbaldehyde