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| | 8-Quinolineboronic acid Basic information | | Synthesis |
| | 8-Quinolineboronic acid Chemical Properties |
| Melting point | >300 °C(lit.) | | Boiling point | 160-165°C | | density | 1.28±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | solubility | soluble in Methanol | | pka | 4.61±0.30(Predicted) | | form | Powder | | color | Yellow to beige | | Merck | 14,8069 | | BRN | 147522 | | InChI | InChI=1S/C9H8BNO2/c12-10(13)8-5-1-3-7-4-2-6-11-9(7)8/h1-6,12-13H | | InChIKey | KXJJSKYICDAICD-UHFFFAOYSA-N | | SMILES | O([H])B(C1C([H])=C([H])C([H])=C2C([H])=C([H])C([H])=NC2=1)O[H] | | CAS DataBase Reference | 86-58-8(CAS DataBase Reference) |
| | 8-Quinolineboronic acid Usage And Synthesis |
| Synthesis | 8-Quinolineboronic acid was prepared as follows: 8-Bromoquinoline (2.08 g, 10 mmol) was dissolved in 30 mL of THF, and then n-butyllithium (4 mL, 2.5 M in hexane) was added at -78 °C. After 1 hour of addition, trimethyl borate (1.23 mL, 11 mmol) was added at the same temperature. The resulting solution was stirred for 5 hours, and then 100 mL of 2 M HCl was added, followed by three extractions using 60 mL of ethyl acetate. The resulting extracts were combined, dehydrated using anhydrous magnesium sulfate, and distilled under reduced pressure. The obtained compound was separated and purified by silica gel column chromatography to produce 1.30 g (yield: 75%) of quinoline-8-boronic acid as a white solid. The obtained compound was confirmed by LC-MS. 
| | Chemical Properties | yellow crystal powder | | Uses | suzuki reaction | | Uses | Reactant involved in:
- C-H and C-S bond activations
- Synthesis of pyridazine via sequential amination / Suzuki coupling / alkylation reactions
- Suzuki-Miyaura coupling reactions for synthesis of biaryl monophosphorus ligands, fused tricyclic oxa-quinolones, or substituted β-amino acids
- Copper-catalyzed azidation with sodium azide
- Studies of the affect of fluoride on the stability of boronic acids during click reactions
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| | 8-Quinolineboronic acid Preparation Products And Raw materials |
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