3-CHLORO-2-METHOXYPHENYLBORONIC ACID

3-CHLORO-2-METHOXYPHENYLBORONIC ACID Property

Boiling point:

356.9±52.0 °C(Predicted)

Density 

1.32±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

7.58±0.58(Predicted)

form 

solid

color 

Off-white

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P271Use only outdoors or in a well-ventilated area.

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

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.

P330Rinse mouth.

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P337+P313IF eye irritation persists: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

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

P405Store locked up.

P501Dispose of contents/container to..…

3-CHLORO-2-METHOXYPHENYLBORONIC ACID Chemical Properties,Usage,Production

Uses

3-Chloro-2-methoxyphenylboronic Acid is a reagent used in the synthesis of a selective 17β-?HSD1 inhibitor in the therapeutic treatment of endometriosis.

Synthesis

General procedure for the synthesis of 3-chloro-2-methoxyphenylboronic acid from 1-bromo-3-chloro-2-methoxybenzene and triisopropyl borate: 1-bromo-3-chloro-2-methoxybenzene (113.2 g, 426.4 mmol) was dissolved in tetrahydrofuran (1000 mL), and cooled to -78°C. At the same temperature 1.7 M tertiary-butyllithium (t-BuLi) was added slowly to a tert-butyl lithium (t-BuLi) ) to a hexane solution (251.7 mL, 426.4 mmol). The reaction mixture was stirred at -78°C for 1 h. Triisopropyl borate (B(OiPr)3) (113.2 mL, 852.4 mmol) was added, followed by gradual warming of the reaction mixture to room temperature and continued stirring for 3 hours. Upon completion of the reaction, 2 N aqueous hydrochloric acid (800 mL) was added to the mixture and stirred at room temperature for 1.5 hours. The resulting precipitate was collected by filtration, washed sequentially with water and ether and dried under vacuum. The crude product was recrystallized by a solvent mixture of chloroform and ethyl acetate and dried to give 3-chloro-2-methoxyphenylboronic acid as a white solid (89.6 g, 91% yield; Mass Spectrometry (MS): [M + H]+ = 230.

References

[1] Patent: KR2018/10165, 2018, A. Location in patent: Paragraph 0207-0210