4-(2-Hydroxyethyl)phenylboronicacid

4-(2-Hydroxyethyl)phenylboronicacid Property

Boiling point:

359.9±44.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

8.82±0.10(Predicted)

Appearance

White to off-white Solid

Safety

HS Code 

2931900090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4-(2-Hydroxyethyl)phenylboronicacid Chemical Properties,Usage,Production

Synthesis

General procedure for the synthesis of (4-(2-hydroxyethyl)phenyl)boronic acid from 4-bromophenylethanol: To a stirred solution of 4-bromophenylethanol (5.00 g, 24.9 mmol) in THF (80 ml) was slowly added a hexane solution (39.8 ml, 59.7 mmol) of 1.5 M n-butyllithium (n-BuLi) at -78 °C for 30 minutes. The reaction temperature was maintained at -78 °C and after 1 h of reaction, a THF (20 ml) solution of triisopropoxyboron (B(OiPr)3, 8.61 ml, 37.3 mmol) was slowly added. The reaction mixture was gradually warmed up to room temperature and treated with 2M hydrochloric acid (HCl, 100 ml) for 1 hour. After completion of the reaction, the reaction mixture was extracted with dichloromethane (CH2Cl2), the organic phase was dried with anhydrous magnesium sulfate (MgSO4) and filtered. The filtrate was concentrated by vacuum evaporation and the residue was purified by silica gel column chromatography with dichloromethane/methanol as eluent (CH2Cl2/MeOH = 20/1, v/v) to afford 2.61 g of the target product (4-(2-hydroxyethyl)phenyl)boronic acid in 63% yield. The product was characterized by 1H-NMR (CD3OD): δ 7.64-7.48 (2H, m), 7.19-7.13 (2H, m), 3.70 (2H, t, J = 7.2 Hz), 2.77 (2H, t, J = 7.2 Hz). Mass spectrum (ESI) m/z: 165 ([MH]-).

References

[1] Patent: US2003/236260, 2003, A1. Location in patent: Page 114
[2] Patent: US2004/19045, 2004, A1. Location in patent: Page 52