2-Furanboronic acid Chemical Properties

Melting point:

112 °C (dec.) (lit.)

Boiling point:

247.7±32.0 °C(Predicted)

Density 

1.25±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

solubility 

Chloroform (Slightly, Sonicated), DMSO (Slightly)

pka

8.29±0.53(Predicted)

form 

Crystalline Powder

color 

Light beige

Water Solubility 

Slightly soluble in water.

Sensitive 

Air Sensitive

BRN 

112370

InChI

InChI=1S/C4H5BO3/c6-5(7)4-2-1-3-8-4/h1-3,6-7H

InChIKey

PZJSZBJLOWMDRG-UHFFFAOYSA-N

SMILES

O1C=CC=C1B(O)O

CAS DataBase Reference

13331-23-2(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39-3

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, AIR SENSITIVE, KEEP COLD

HS Code 

29321900

MSDS

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

2-Furanboronic acid Usage And Synthesis

Chemical Properties

light beige crystalline powder

Uses

It is used in Suzuki reaction for generalized route for the synthesis of β-furyl-α,β-unsaturated aldehydes.

Synthesis

The general procedure for the synthesis of 2-furanboronic acid from 2-(furan-2-yl)-6-methyl-1,3,6,2-dioxaborolane-4,8-dione was as follows: a solution of MIDA borate (5 mmol) in THF (50 mL) was added to a 100 mL flask fitted with a stir bar under an ambient atmosphere followed by the addition of an aqueous 1.0 M NaOH solution (15 mL ). The reaction mixture was stirred vigorously for 20 minutes. Upon completion, the mixture was transferred to a partition funnel and diluted with ether (50 mL) and 0.5 M pH 7 sodium phosphate buffer (50 mL). The phases were separated after sufficient shaking. The aqueous phase was extracted with a solvent mixture of THF/ether (1:1, 2 x 25 mL). The organic phases were combined, dried with anhydrous MgSO4, filtered and concentrated in vacuum. The residual solvent was co-evaporated with acetonitrile and the resulting solid was dried under vacuum at about 1 Torr for 30 min. The resulting boric acid was analyzed by 1H-NMR to be >95% pure and was immediately used in the subsequent cross coupling reaction. Specific examples are as follows: 2-furanboronic acid (0.531 g, 95% yield) was obtained as an off-white solid using MIDA borate (1.127 g, 5.002 mmol) following the general procedure described above.TLC (unfolding reagent: ethyl acetate) Rf = 0.46, stained with potassium permanganate to develop color.1H-NMR (500 MHz, DMSO-d6:D2O 1H-NMR (500 MHz, DMSO-d6:D2O 95:5, with TMS) δ 7.81 (dd, J = 1.5, 5.5 Hz, 1H), 7.07 (dd, J = 3.0, 0.5 Hz, 1H), 6.48 (dd, J = 3.5, 2.0 Hz, 1H). 13C-NMR (125 MHz, DMSO-d6:D2O 95:5, with TMS) δ 146.4, 121.5, 110.3. 121.5, 110.3. HRMS (EI+) calculated value C4H3O3B [M]+: 112.0332, measured value: 112.0332.

References

[1] Journal of the American Chemical Society, 2009, vol. 131, p. 6961 - 6963
[2] Patent: WO2010/36921, 2010, A2. Location in patent: Page/Page column 41

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