4-(Dimethylamino)phenylboronic acid Chemical Properties

Melting point:

227 °C(lit.)

Boiling point:

329.9±44.0 °C(Predicted)

Density 

1.12±0.1 g/cm3(Predicted)

storage temp. 

0-6°C

pka

8.78±0.10(Predicted)

form 

Crystalline Powder

color 

White to green-gray or blue-gray

Water Solubility 

Sparingly soluble in water. (~2.5%)

InChI

InChI=1S/C8H12BNO2/c1-10(2)8-5-3-7(4-6-8)9(11)12/h3-6,11-12H,1-2H3

InChIKey

RIIPFHVHLXPMHQ-UHFFFAOYSA-N

SMILES

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

CAS DataBase Reference

28611-39-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

Hazard Note 

Irritant

HazardClass 

IRRITANT, AIR SENSITIVE, KEEP COLD

HS Code 

29319090

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

4-(Dimethylamino)phenylboronic acid Usage And Synthesis

Chemical Properties

white to green-grey or blue-grey crystalline

Uses

suzuki reaction

Uses

4-(Dimethylamino)phenylboronic Acid can be used as reactant/reagent in preparation of biaryls via palladium-catalyzed Suzuki-Miyaura coupling of nitroarenes with boronic acids.

Synthesis

Under argon protection, 20 g (100 mmol) of 4-bromo-N,N-dimethylaniline was dissolved in 400 mL of anhydrous tetrahydrofuran and the mixture was cooled to -40°C. The reaction was carried out with the aid of a liquid solution of 1.6 M n-butyllithium in hexane. Subsequently, 63 mL (100 mmol) of a hexane solution of 1.6 M n-butyllithium was slowly added dropwise, stirring was maintained and the reaction mixture was gradually warmed to 0 °C for 1 hour. The reaction mixture was again cooled to -78 °C and 50 mL of anhydrous tetrahydrofuran was added. A solution containing 26 g (250 mmol) of trimethyl borate was added dropwise, followed by raising the reaction mixture to room temperature and stirring for 5 hours. After completion of the reaction, 200 mL of 1 N hydrochloric acid solution was added and stirred for 1 h. The aqueous layer was separated and discarded. The organic layer was dried with anhydrous magnesium sulfate and subsequently concentrated under reduced pressure. The resulting solid was washed with toluene to afford 12.38 g (75 mmol) of the target product 4-(N,N-dimethylamino)phenylboronic acid in 75% yield.

References

[1] Patent: CN108276337, 2018, A. Location in patent: Paragraph 0057; 0058; 0059

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