| Identification | More | [Name]
4-Biphenylboronic acid | [CAS]
5122-94-1 | [Synonyms]
(1,1'-BIPHENYL-4-YL)BORONIC ACID
4-BIPHENYLBORONIC ACID
4-BIPHENYLYLBORONIC ACID
4-PHENYLBENZENEBORONIC ACID
4-PHENYLPHENYLBORONIC ACID
AKOS BRN-0030
BIPHENYL-4-BORONIC ACID
RARECHEM AH PB 0261
4-Biphenylboric acid
4-Biphenylboronic acid, 98+%
4-Diphenyl Boric Acid
Biphenyl-4-boronic acid 98%
4-Biphenylboronic Acid (contains varying amounts of Anhydride)
Biphenyl-4-boronic acid, 98+% | [EINECS(EC#)]
675-084-0 | [Molecular Formula]
C12H11BO2 | [MDL Number]
MFCD00093311 | [Molecular Weight]
198.03 | [MOL File]
5122-94-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
232-245 °C (lit.) | [Boiling point ]
385.5±35.0 °C(Predicted) | [density ]
1.18±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,Room Temperature | [solubility ]
soluble in Acetone,Methanol | [form ]
Powder | [pka]
8.61±0.10(Predicted) | [color ]
White | [Water Solubility ]
Insoluble in water. | [Usage]
Intermediates of Liquid Crystals | [Detection Methods]
HPLC,NMR | [BRN ]
2937410 | [InChI]
InChI=1S/C12H11BO2/c14-13(15)12-8-6-11(7-9-12)10-4-2-1-3-5-10/h1-9,14-15H | [InChIKey]
XPEIJWZLPWNNOK-UHFFFAOYSA-N | [SMILES]
B(C1=CC=C(C2=CC=CC=C2)C=C1)(O)O | [CAS DataBase Reference]
5122-94-1(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Chemical Properties]
Solid | [Uses]
Intermediates of Liquid Crystals | [Uses]
suzuki reaction | [Uses]
Used in Suzuki reactions and as intermediates of liquid crystals. | [Synthesis]
The general procedure for the synthesis of 4-biphenylboronic acid from 4-bromobiphenyl was as follows: 4-bromobiphenyl (30 g, 0.12 mol) was added to a single-neck flask and the reaction was carried out under argon protection. Tetrahydrofuran (THF) (500 mL) was added and stirred at -78 °C for 10 min. Slowly n-butyllithium (2.5 M in hexane) (77 mL, 0.19 mol) was added and the mixture was stirred at -78 °C for 1 hour. Subsequently, dimethyl borate (21.9 mL, 0.19 mol) was added at -78 °C and stirring was continued at -78 °C for 30 min, then brought to room temperature and stirred for 4 hours. After completion of the reaction, extraction was carried out with distilled water and ethyl acetate (EA) and the organic layer was dried with anhydrous magnesium sulfate (MgSO4). The solvent was removed using a rotary evaporator. Finally, pure 4-biphenylboronic acid (21 g, 84% yield) was isolated by column chromatography using hexane and ethyl acetate (EA) as eluents. | [References]
[1] Patent: WO2011/105700, 2011, A1. Location in patent: Page/Page column 18; 19; 21; 22
[2] Angewandte Chemie - International Edition, 2006, vol. 45, # 9, p. 1404 - 1408
[3] Tetrahedron, 2007, vol. 63, # 20, p. 4297 - 4303
[4] Journal of Organic Chemistry, 2011, vol. 76, # 4, p. 1013 - 1030
[5] Journal of the Chemical Society [Section] C: Organic, 1966, p. 566 - 571 |
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