3-Aminobenzeneboronic acid Chemical Properties

Melting point:

225 °C

Boiling point:

376.0±44.0 °C(Predicted)

Density 

1.23±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder or crystals

pka

pK1: 4.46;pK2: 8.81 (25°C)

color 

Off-white to light brown

Water Solubility 

Soluble in water (partly miscible).

InChI

InChI=1S/C6H8BNO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H,8H2

InChIKey

JMZFEHDNIAQMNB-UHFFFAOYSA-N

SMILES

B(C1=CC=CC(N)=C1)(O)O

CAS DataBase Reference

30418-59-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36/37/39-37

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29310095

3-Aminobenzeneboronic acid Usage And Synthesis

Chemical Properties

hexagonal plates

Uses

3-Aminobenzeneboronic acid is used as an organic chemical synthesis intermediate. It is a boronic acid with potential use for biochemical research.

Uses

3-Aminobenzeneboronic acid is a boronic acid with potential use for biochemical research,it ie also used for suzuki reaction.

Synthesis

General method: 3-nitrophenylboronic acid (1 eq.), hexafluoroisopropanol (HFIP, 10 eq.) and iron powder (5 eq.) were added to the reaction tube and mixed. Subsequently, 2N aqueous hydrochloric acid solution was added dropwise to the reaction mixture. The reaction mixture was stirred at room temperature for 30 minutes and then neutralized with saturated aqueous sodium bicarbonate (NaHCO3). The organic layer was extracted three times with saturated aqueous sodium bicarbonate solution and combined. The organic layer was subsequently washed with brine, dried over anhydrous sodium sulfate (Na2SO4), filtered, and concentrated under reduced pressure. Finally, the crude product was purified by silica gel column chromatography to afford the target compound 3-aminophenylboronic acid.

References

[1] Tetrahedron Letters, 2017, vol. 58, # 37, p. 3646 - 3649
[2] Journal of the American Chemical Society, 1932, vol. 54, p. 4415,4418
[3] Journal of Organic Chemistry, 1937, vol. 2, p. 522,533
[4] Journal of the American Chemical Society, 1931, vol. 53, p. 713
[5] Patent: US2007/209123, 2007, A1. Location in patent: Page/Page column 7

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