3-Bromothiophene-2-carboxylic acid Chemical Properties

Melting point:

197-201 °C(lit.)

Boiling point:

318.0±27.0 °C(Predicted)

Density 

1.923±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

form 

powder to crystal

pka

3.09±0.10(Predicted)

color 

White to Almost white

BRN 

121585

CAS DataBase Reference

7311-64-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

43-36/37/38

Safety Statements 

36/37-37/39-26

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29349990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

3-Bromothiophene-2-carboxylic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Synthesis

Under nitrogen protection, 2,3-dibromothiophene (12.1 g, 0.025 mol) was dissolved in anhydrous ether (15 mL) and cooled to -78°C. A solution of n-butyllithium (2.5 M, 22 mL, 0.055 mol) in ether was slowly added dropwise. After the dropwise addition, stirring was continued at -78 °C for 10 minutes. Subsequently, gaseous carbon dioxide was passed into the reaction system and a white precipitate was immediately observed to form. After keeping the reaction at -78 °C for 30 min, the reaction was slowly warmed up to room temperature. Upon completion of the reaction, the reaction was quenched with Milli-Q water and the aqueous phase was extracted with 10% sodium hydroxide solution (3 x 50 mL). The aqueous phase was combined, acidified with 6 N hydrochloric acid and the precipitate precipitated was collected by filtration. The resulting solid was recrystallized with ethanol (50 mL) and water (200 mL) and dried in vacuum to give the white powdery product 3-bromothiophene-2-carboxylic acid (9.23 g). The product was analyzed by 19F NMR, mass spectrometry (70 eV, EI): m/z 208 (M-1), 1H NMR (CDCl3): δ 7.81 (d, 1H, J=5.2 Hz), 7.19 (d, 1H, J=5.2 Hz) and 13C NMR (CDCl3): δ 117.6, 133.8, 134.6, 162.6, 207.6 Confirmed structure.

References

[1] Chemical Communications, 2011, vol. 47, # 43, p. 11840 - 11842
[2] Patent: WO2012/156948, 2012, A1. Location in patent: Page/Page column 21-22
[3] Synthesis, 1980, # 4, p. 327 - 329
[4] Archiv der Pharmazie, 1998, vol. 331, # 12, p. 405 - 411

3-Bromothiophene-2-carboxylic acid(7311-64-0)Related Product Information

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• Methyl 4-(bromomethyl)benzoate
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• Tetrahydrothiophene
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• METHYL 3-BROMOTHIOPHENE-2-CARBOXYLATE
• 4,5-DIBROMOTHIOPHENE-2-CARBOXYLIC ACID
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• Methyl 4-bromothiophene-2-carboxylate
• 5-BROMOTHIOPHENE-2-CARBOXYLIC ACID
• METHYL4,5-DIBROMOTHIOPHENE-2-CARBOXYLATE
• 4-BROMOTHIOPHENE-3-CARBOXYLIC ACID
• 4-Bromo-2-thiophenecarboxylic acid