| Identification | More | [Name]
8-Quinolineboronic acid | [CAS]
86-58-8 | [Synonyms]
8-QUINOLINEBORONIC ACID
8-QUINOLINEBORONIC ACID, DIMER
8-QUINOLINYLBORONIC ACID
QUINOLIN-8-YLBORONIC ACID
QUINOLINE-8-BORONIC ACID
RARECHEM AH PB 0127
TIMTEC-BB SBB003824
8-QUINOLINEBORONIC ACID 95%
Quinoline-8-boronicacid,99%
8-Quinolineboronic
8-quindineboronic acid
8-QUINOLINBORONIC ACID
Quinolin-8-yl-8-boronic acid | [EINECS(EC#)]
626-756-7 | [Molecular Formula]
C9H8BNO2 | [MDL Number]
MFCD01114698 | [Molecular Weight]
172.98 | [MOL File]
86-58-8.mol |
| Questions And Answer | Back Directory | [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. 
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| Chemical Properties | Back Directory | [Appearance]
yellow crystal powder | [Melting point ]
>300 °C(lit.) | [Boiling point ]
160-165°C | [density ]
1.28±0.1 g/cm3(Predicted) | [storage temp. ]
0-6°C | [solubility ]
soluble in Methanol | [form ]
Powder | [pka]
4.61±0.30(Predicted) | [color ]
Yellow to beige | [Detection Methods]
HPLC | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R36/38:Irritating to eyes and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HazardClass ]
IRRITANT | [HS Code ]
29334900 |
| Hazard Information | Back Directory | [Chemical Properties]
yellow crystal powder | [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
| [Uses]
suzuki reaction |
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