3-Chloro-4-methylphenylboronic acid

3-Chloro-4-methylphenylboronic acid Property

Melting point:

210-216°C

Boiling point:

317.3±52.0 °C(Predicted)

Density 

1.26±0.1 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

soluble in Methanol

pka

7.82±0.10(Predicted)

form 

Crystalline Powder of Flakes

color 

White

InChIKey

YTJUYWRCAZWVSX-UHFFFAOYSA-N

CAS DataBase Reference

175883-63-3(CAS DataBase Reference)

Safety

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-20/21/22

Safety Statements 

26-36/37/39-36-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29163990

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.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

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

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.

P405Store locked up.

3-Chloro-4-methylphenylboronic acid Chemical Properties,Usage,Production

Chemical Properties

White solid

Uses

suzuki reaction

Synthesis

GENERAL PROCEDURE: To a tetrahydrofuran (THF, 4 mL) solution of diisopropylaminoborane (DIPAB, 863 mg, 7.5 mmol) and magnesium (Mg, 182 mg, 7.5 mmol) was added a 1 M solution of phenylmagnesium bromide (PhMgBr) THF (375 μL, 375 μmol) at room temperature. After 10 min of reaction, 30 mL of anhydrous THF was added, followed by 4-bromo-2-chlorotoluene (5 mmol). The reaction mixture was cooled to 0 °C and quenched by slowly adding 7 mL of methanol (MeOH). After 1 h of reaction, the volatiles were removed under reduced pressure and the resulting solid was dissolved in a 1 N hydrochloric acid/methanol (7:3, v/v) mixture. After 1 h of reaction at room temperature, 100 mL of ethyl acetate (AcOEt) was added, and the organic phase was washed sequentially with 1N hydrochloric acid (30 mL) and saturated saline (3 x 30 mL). The organic phase was concentrated under reduced pressure to give a solid product, which was finally purified by recrystallization from water (H2O) to give 3-chloro-4-methylphenylboronic acid.

References

[1] Tetrahedron, 2019, vol. 75, # 2, p. 164 - 171