Boronic acid, (5-cyano-2-methoxyphenyl)- (9CI)

Boronic acid, (5-cyano-2-methoxyphenyl)- (9CI) Property

Melting point:

211-212°

Boiling point:

412.4±55.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,2-8°C

pka

7.19±0.58(Predicted)

Appearance

Off-white to light yellow Solid

Safety

HazardClass 

IRRITANT

HS Code 

2931900090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

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

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

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.

P312Call a POISON CENTER or doctor/physician if you feel unwell.

P403+P233Store in a well-ventilated place. Keep container tightly closed.

Boronic acid, (5-cyano-2-methoxyphenyl)- (9CI) Chemical Properties,Usage,Production

Synthesis

The general procedure for the synthesis of 2-methoxy-5-cyanophenylboronic acid from triisopropyl borate and 3-bromo-4-methoxybenzonitrile was as follows: firstly, 3-bromo-4-methoxybenzonitrile (7.7 g, 36 mmol) and triisopropyl borate (14 g, 73 mmol) were dissolved in tetrahydrofuran (150 mL), and then at -78 °C, 2.5 mol/L of n butyl lithium (hexane solution, 22 mL, 55 mmol), and the addition process lasted for 20 min. After the reaction mixture was stirred at -78 °C for 2 h, 7% phosphoric acid (100 mL) was added and the mixture was gradually warmed to room temperature. Subsequently, the reaction mixture was partitioned by adding dichloromethane to the organic layer and extracting the mixture with 5% aqueous sodium hydroxide (200 mL). The aqueous layer was washed with ether and adjusted to pH 2.5 with 85% phosphoric acid and the insoluble material was collected by filtration. The resulting solid was washed with water and dried to give the final 2-methoxy-5-cyanophenylboronic acid (5.1 g, 29 mmol, 79% yield). The product was detected by mass spectrometry (ESI) at m/z 178 (M+H)+; 1H NMR (300 MHz, DMSO-d6) δ 8.03 (s, 2H), 7.86-7.78 (m, 2H), 7.13 (d, J=11.6 Hz, 1H), 3.85 (s, 3H).

References

[1] Patent: US2016/332999, 2016, A1. Location in patent: Paragraph 0649; 0650; 0651
[2] Patent: EP3330266, 2018, A1. Location in patent: Paragraph 0169