3-Thiopheneboronic acid Chemical Properties

Melting point:

164-169 °C (lit.)

Boiling point:

287.9±32.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

soluble in Methanol

pka

8.25±0.10(Predicted)

form 

Powder

color 

Almost white to grayish

BRN 

113573

InChI

InChI=1S/C4H5BO2S/c6-5(7)4-1-2-8-3-4/h1-3,6-7H

InChIKey

QNMBSXGYAQZCTN-UHFFFAOYSA-N

SMILES

C1SC=CC=1B(O)O

CAS DataBase Reference

6165-69-1(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,Xi

Risk Statements 

22-36/37/38

Safety Statements 

26-37/39-36

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, IRRITANT-HARMFUL, KEEP COLD

HS Code 

29339900

MSDS

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

3-Thiopheneboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powder

Uses

suzuki reaction

Uses

3-Thiopheneboronic Acid is used in the synthesis of porphyrins as inhibitiors of telomerase. It is also used to prepare 1,4-disubstituted imidazoles as potential antibacterial agents.

Synthesis

General procedure for the synthesis of 3-thiophene boronic acid from 3-bromothiophene: Triphenylphosphine (0.131 g, 0.5 mmol, 20 mol%), p-iodoiodobenzene (0.585 g, 2.5 mmol), and triethylamine (1.78 mL, 12.5 mmol) were added sequentially to a 50 mL round-bottomed flask (equipped with a side arm, a condenser, and a stir bar). The reaction system was degassed by alternating vacuum and argon filling three times. Palladium dichloride (0.023 g, 0.13 mmol, 5 mol%) was added under positive argon pressure. After stirring for 15 minutes at room temperature, diisopropylaminoborane (5 mL, 1 M THF solution, 5 mmol) was added and the reaction mixture was again degassed by alternating vacuum and argon filling three times. The reaction solution was heated to reflux and kept at reflux for 12 hours. Upon completion of the reaction, the reaction solution was cooled to 0 °C and 6 mL of methanol was slowly added (note: this is an exothermic reaction, which releases hydrogen). After stirring for 15 minutes, all solvent was removed by distillation under reduced pressure to give a black solid. The solid was dissolved in 3M sodium hydroxide solution (8 mL) and subsequently washed with hexane (3 x 10 mL). The aqueous layer was cooled to 0°C (ice bath) and acidified with concentrated hydrochloric acid to pH ≤ 1, at which point 3-thiopheneboronic acid precipitated as a white solid. The aqueous layer was extracted with ether (3 x 10 mL), the organic phases were combined, dried with magnesium sulfate and filtered. Finally, the solvent was removed by distillation under reduced pressure to obtain 3-thiopheneboronic acid in white solid form.

References

[1] Journal of Medicinal Chemistry, 2005, vol. 48, # 1, p. 224 - 239
[2] Organic Letters, 2011, vol. 13, # 17, p. 4479 - 4481
[3] Journal of Organic Chemistry, 2013, vol. 78, # 13, p. 6427 - 6439
[4] Patent: US6342610, 2002, B2. Location in patent: Page column 77
[5] Tetrahedron, 2011, vol. 67, # 3, p. 576 - 583

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