4,4'-Biphenyldiboronic acid Chemical Properties

Melting point:

300 °C (dec.)(lit.)

Boiling point:

505.9±60.0 °C(Predicted)

Density 

1.31±0.1 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

pka

8.25±0.17(Predicted)

color 

White to Green to Brown

Water Solubility 

Soluble in water.

BRN 

2941876

InChIKey

SLHKDOGTVUCXKX-UHFFFAOYSA-N

CAS DataBase Reference

4151-80-8(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn,C

Risk Statements 

36/37/38-22

Safety Statements 

37/39-26-`37

WGK Germany 

3

Hazard Note 

Corrosive

HS Code 

29163990

MSDS

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

4,4'-Biphenyldiboronic acid Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

Reactant involved in synthesis of:

• Organic field-effect transistors based on organic semiconductors containing diazaboroles
• Cycloparaphenylenes via Suzuki coupling
• 1,3,2-Diazaboroine derivatives for organic thin-film transistor applications
• Back-to-back coupled 2,6-bis(triazol-1-yl)pyridine molecules
• Rectangular host via electrochemical reactions with methylaquacobaloxime and diamine
• Arylboronates from reactions with catechol, dihydroxynaphthalene and diaminobenzenedithiol for use as organic field-effect transistors and light emitting diodes

Synthesis

The general procedure for the synthesis of 4,4'-biphenyl diboronic acid from 4,4'-dibromobiphenyl was as follows: to a solution of 4,4'-dibromo-1,1'-biphenyl (5.00 g, 16.03 mmol) in anhydrous THF (100 mL) was added slowly and dropwise n-butyllithium (1.0 M hexanes solution, 40.1 mL, 64.1 mmol) at -78 °C, and was stirred for 1 hour. Subsequently, the reaction mixture was slowly warmed to -30 °C and trimethyl borate (4.83 mL, 43.3 mmol) was added dropwise and then stirring was continued for 1 hour at room temperature. Upon completion of the reaction, the reaction mixture was acidified to pH=2 with 1.5 N HCl. The resulting precipitate was filtered to afford 4,4'-biphenyldiboronic acid in the form of an off-white solid (2.5 g, 10.34 mmol, 64.5% yield). The structure of the product was confirmed by NMR (DMSO-d6, δ=2.50 ppm, 400 MHz): δ 8.06 (broad peak, 4H), 7.88 (double peak, J=8.53 Hz, 4H), 7.65 (double peak, J=8.4 Hz, 4H).

References

[1] Patent: WO2015/5901, 2015, A1. Location in patent: Page/Page column 490
[2] Chemistry Letters, 2008, vol. 37, # 11, p. 1122 - 1123
[3] Journal of Materials Chemistry, 2011, vol. 21, # 18, p. 6607 - 6613
[4] Journal of Materials Chemistry, 2012, vol. 22, # 10, p. 4502 - 4510
[5] Angewandte Chemie - International Edition, 2014, vol. 53, # 51, p. 14144 - 14148

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