4-Butylphenylboronic acid Chemical Properties

Melting point:

91-97 °C(lit.)

Boiling point:

313.5±35.0 °C(Predicted)

Density 

1.03±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

solubility 

Soluble in methanol.

form 

powder to crystal

pka

8.78±0.10(Predicted)

color 

White to Orange to Green

BRN 

6920034

CAS DataBase Reference

145240-28-4(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,F

Risk Statements 

36/37/38-10

Safety Statements 

26-36/37/39-16-7/9-24/25

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

29319090

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ALFA

4-Butylphenylboronic acid Usage And Synthesis

Chemical Properties

White powder

Uses

Reactant for Suzuki-Miyaura cross-couplings, NHC-Iron-catalyzed aerobic oxidative aromatic esterification of aldehydes, Palladium-catalyzed oxidative Heck-type reactions.

Uses

Intermediates of Liquid Crystals

Uses

suzuki reaction

Synthesis

A. Synthesis of 4-n-butylphenylboronic acid To a mixed solution of tetrahydrofuran (32 mL) and ether (96 mL) of 1-bromo-4-n-butylbenzene (6.24 g, 29.3 mmol) was added dropwise n-butyllithium (1.6 M hexane solution, 21.9 mL, 35.1 mmol) at -78 °C. The reaction mixture was stirred at -78 °C for 30 min, and then slowly added dropwise over 20 min to a solution of trimethyl borate (6.1 g, 58.6 mmol) in ether (64 mL) pre-cooled to -78 °C. After the dropwise addition was completed, the reaction mixture was continued to be stirred at -78 °C for 30 minutes, then slowly warmed to room temperature and stirred overnight. After the reaction was completed, 10% aqueous hydrochloric acid solution (150 mL) was added, shaken vigorously for 10 minutes, and left to stratify. The ether layer was separated and the aqueous layer was extracted with ether (100 mL). All organic phases were combined and extracted with 1N sodium hydroxide solution (3 x 100mL). Combine the alkaline aqueous phases, wash once with ether, then acidify to pH 1 with 6N hydrochloric acid and extract with ether (3 x 100mL). All organic phases were combined, washed with water, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure to afford the target product 4-n-butylphenylboronic acid (2.0 g, 38% yield).

References

[1] Patent: US5514696, 1996, A
[2] Advanced Functional Materials, 2017, vol. 27, # 45,

4-Butylphenylboronic acid(145240-28-4)Related Product Information

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