| Identification | More | [Name]
4,4'-Biphenyldiboronic acid | [CAS]
4151-80-8 | [Synonyms]
4,4'-BIPHENYLDIBORONIC ACID
4,4-BIPHENYLDIBORONIC ACID
BIPHENYL-4,4'-DIBORONIC ACID
RARECHEM AH PB 0032
4,4'-Biphenyldiboronicacid,97%
4,4'-biphenylenediboronic acid
4,4'-Biphenyldiboronic acid
4,4'-Biphenylboronic acid | [Molecular Formula]
C12H12B2O4 | [MDL Number]
MFCD00151795 | [Molecular Weight]
241.84 | [MOL File]
4151-80-8.mol |
| Chemical Properties | Back Directory | [Appearance]
white to light yellow crystal powde | [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 Data | Back Directory | [Hazard Codes ]
Xn,C | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S37/39:Wear suitable gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
3
| [Hazard Note ]
Corrosive | [HS Code ]
29163990 |
| Hazard Information | Back Directory | [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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