| Identification | More | [Name]
2-Bromopyridine-5-boronic acid | [CAS]
223463-14-7 | [Synonyms]
2-BROMO-5-PYRIDINEBORONIC ACID
2-BROMOPYRIDINE-5-BORONIC ACID
2-BROMOPYRIDYL-5-BORONIC ACID
6-BROMO-3-PYRIDINEBORONIC ACID
(6-BROMO-3-PYRIDINYL)-BORONIC ACID
6-BROMOPYRIDIN-3-YL-3-BORONIC ACID
(6-BROMOPYRIDIN-3-YL)BORONIC ACID
6-BROMOPYRIDINE-3-BORONIC ACID
AKOS BRN-0200
RARECHEM AK ML 0443
6-BROMOPYRIDIN-3-LBORONIC ACID
2-Bromopyridine-5-Boronic
2-bromo-5-pyridylboronic acid
2-Bromopyridine-5-boronic acid 97%
2-BROMOPYRIDIN-5-LBORONIC ACID
2-Bromo-5-pyridineboronic Acid (contains varying amounts of Anhydride)
2-Bromopyridine-5-boronic acid ,96% | [EINECS(EC#)]
672-028-7 | [Molecular Formula]
C5H5BBrNO2 | [MDL Number]
MFCD03411558 | [Molecular Weight]
201.81 | [MOL File]
223463-14-7.mol |
| Chemical Properties | Back Directory | [Melting point ]
161-166 °C | [Boiling point ]
358.2±52.0 °C(Predicted) | [density ]
1.78±0.1 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [solubility ]
soluble in Methanol | [form ]
solid | [pka]
6.62±0.10(Predicted) | [color ]
white to off-white | [Detection Methods]
HPLC,NMR | [BRN ]
9119918 | [InChI]
1S/C5H5BBrNO2/c7-5-2-1-4(3-8-5)6(9)10/h1-3,9-10H | [InChIKey]
BCYWDUVHAPHGIP-UHFFFAOYSA-N | [SMILES]
OB(O)c1ccc(Br)nc1 | [CAS DataBase Reference]
223463-14-7(CAS DataBase Reference) | [Storage Precautions]
Store under nitrogen |
| Hazard Information | Back Directory | [Chemical Properties]
Off-white solid | [Uses]
Reactant involved in:
- Iterative cross-coupling reactions for synthesis of non-cytotoxic terpyridines
- The Garlanding approach for synthesis of phenyl-pyridyl scaffolds
- Cyanation for synthesis of aromatic nitriles
- Suzuki-Miyaura cross-coupling with dihalopyridines and dihalobipyridines
- Petasis boronic Mannich reaction
| [General Description]
May contain varying amounts of anhydride | [Synthesis]
General procedure for the synthesis of 2-bromopyridine-5-boronic acid from 2,5-dibromopyridine and triisopropyl borate:
1. 2,5-dibromopyridine (2.37 g, 10 mmol) was dissolved in 90 mL of ether/THF (8:1) at -78 °C and 7.5 mL of n-BuLi (1.6 M hexane solution) was added dropwise slowly. After the dropwise addition was completed, the reaction mixture was continued to be stirred at -78°C for 2 hours.
2. Triisopropyl borate (4.49 g, 24 mmol) was added and the reaction mixture was stirred at -78 °C for 2 h, followed by slow warming to room temperature.
3. The reaction was quenched with 10 mL of water and stirring was continued overnight.
4. The organic solvent was evaporated and the remaining aqueous layer was adjusted to pH 10 with 5% NaOH and washed with ether (30 mL x 3).
5. The aqueous layer was carefully acidified to pH 4 with 48% HBr to precipitate the target product 2-bromopyridine-5-boronic acid (1.46 g, 72%).
NMR data (300 MHz, DMSO-d6): δ 8.68 (dd, J = 2.1, 0.7 Hz, 1H), 8.53 (br.s, 2H), 8.05 (dd, J = 2.1, 7.8 Hz, 1H), 7.67 (dd, J = 7.8, 0.7 Hz, 1H). | [References]
[1] Patent: WO2012/125832, 2012, A2. Location in patent: Page/Page column 80 |
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