4,4,5,5-tetraMethyl-2-[1,1':3',1''-terphenyl]-3-yl-1,3,2-dioxaborolane

4,4,5,5-tetraMethyl-2-[1,1':3',1''-terphenyl]-3-yl-1,3,2-dioxaborolane Property

Melting point:

101 °C

Boiling point:

507.9±29.0 °C(Predicted)

Density 

1.10±0.1 g/cm3(Predicted)

storage temp. 

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

form 

powder to crystal

color 

White to Almost white

CAS DataBase Reference

1115023-84-1

Safety

HS Code 

2931.90.6000

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.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

4,4,5,5-tetraMethyl-2-[1,1':3',1''-terphenyl]-3-yl-1,3,2-dioxaborolane Chemical Properties,Usage,Production

Synthesis

3-Bromo-1,1':3',1''-terphenyl (26.60 g, 86.03 mmol, 1.0 eq.) and pinacol ester of biphenylboronic acid (103.23 g, 1.2 eq.) were added to a 1 L three-necked round-bottomed flask with potassium acetate (25.33 g, 3 eq.) and bis(diphenylphosphino)ferrocene(II) dichlorodichloromethane complex ( 2.11 g, 0.03 eq.). After the system was degassed and nitrogen displaced, 300 mL of cyclopentyl methyl ether was added under nitrogen atmosphere. Subsequently, the mixture was heated to 100 °C and refluxed with stirring. The heating was stopped after 3 h. The reaction mixture was extracted three times with toluene. The organic layers were combined, dried by adding anhydrous sodium sulfate and allowed to stand for a period of time. After removal of sodium sulfate by filtration, the solution was concentrated under reduced pressure. The oil obtained was purified by activated carbon column chromatography using toluene as eluent. The fraction containing the desired product 3-boronic acid pinacol ester-3′-phenyl-biphenyl was collected and concentrated under reduced pressure. The yellow oil obtained was dissolved in hot methanol and allowed to stand at room temperature before cooling in an ice bath. The precipitated needle-like crystals were collected to afford the target product P3Bpin (Yield: 28.48 g, Yield: 92.9%).

References

[1] Patent: JP2016/88927, 2016, A. Location in patent: Paragraph 0211; 0213
[2] Patent: US2018/94000, 2018, A1. Location in patent: Paragraph 0506
[3] Patent: KR2016/11036, 2016, A. Location in patent: Paragraph 0263 - 0267
[4] Patent: KR2015/135070, 2015, A. Location in patent: Paragraph 0204-0207
[5] Patent: KR2016/19747, 2016, A. Location in patent: Paragraph 0224-0227