5-TERT-BUTOXYCARBONYLTHIOPHENE-2-BORONIC ACID Chemical Properties

Boiling point:

391.1±52.0 °C(Predicted)

Density 

1.24±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

pka

7.90±0.53(Predicted)

Safety Information

HS Code 

2934999090

5-TERT-BUTOXYCARBONYLTHIOPHENE-2-BORONIC ACID Usage And Synthesis

Uses

5-tert-Butoxycarbonylthiophene-2-boronic Acid is used as a reactant in the synthesis of oxotetrahydrofuropyrrolyl derivatives as cathepsin inhibitors.

Synthesis

General procedure for the synthesis of (5-(tert-butoxycarbonyl)thiophen-2-yl)boronic acid from tert-butyl 5-bromothiophene-2-carboxylate and triisopropyl borate: tert-butyl 5-bromothiophene-2-carboxylate (19 g, 72 mmol) was added drop-wise to tetrahydrofuran (THF, 400 mL) solution of tert-butyl 5-bromothiophene-2-carboxylate (29 mL, 72 mmol) at -78 °C. After dropwise addition, the reaction mixture was continued to be stirred for 30 min, followed by slow addition of triisopropyl borate (15 g, 79 mmol). After 2 hours of reaction, the reaction was quenched by the addition of saturated aqueous ammonium chloride (NH4Cl, 100 mL) and the mixture was gradually warmed to room temperature. Upon completion of the reaction, the organic and aqueous layers were separated, and the organic layer was dried over anhydrous sodium sulfate (Na2SO4), concentrated and purified by silica gel column chromatography (eluent: 0-75% ethyl acetate/hexanes) to afford the target product, (5-(tert-butoxycarbonyl)thiophen-2-yl)boronic acid (8.9 g, 56% yield), as a brown solid. Its 1H NMR (500 MHz, DMSO-d6) data were as follows: δ 7.71 (d, J=3.5 Hz, 1H), 7.49 (d, J=3.5 Hz, 1H), 1.49 (s, 9H).

References

[1] Patent: WO2007/18941, 2007, A2. Location in patent: Page/Page column 116-117

5-TERT-BUTOXYCARBONYLTHIOPHENE-2-BORONIC ACID(925921-29-5)Related Product Information

• 5-Hydroxymethylthiophene-2-boronic acid
• THIOPHENE-2-CARBOXYLIC ACID METHYL ESTER-5-BORIC ACID
• 5-Carboxythiophene-2-boronic acid
• 5-PROPIONYL-2-THIOPHENEBORONIC ACID
• 5-Formyl-2-thiopheneboronic acid
• 5-TERT-BUTOXYCARBONYLTHIOPHENE-2-BORONIC ACID