| Identification | More | [Name]
3-Quinolineboronic acid | [CAS]
191162-39-7 | [Synonyms]
3-QUINOLINEBORONIC ACID
3-QUINOLINYLBORONI ACID
3-QUINOLINYLBORONIC ACID
3-QUINOLYL BORONIC ACID
AKOS BRN-0151
CHEMBRDG-BB 4003837
QUINOLIN-3-YLBORONIC ACID
QUINOLINE-3-BORONIC ACID
RARECHEM AK VD 0023
3-Quinolineboronic
Quinoline-3-boronic Acid (contains varying amounts of Anhydride)
Quinolin-3-yl-3-boronic acid
3-Quinolineboronic acid ,97% | [EINECS(EC#)]
640-162-5 | [Molecular Formula]
C9H8BNO2 | [MDL Number]
MFCD02183527 | [Molecular Weight]
172.98 | [MOL File]
191162-39-7.mol |
| Chemical Properties | Back Directory | [Appearance]
light pink or orange to light brown powder | [Melting point ]
148-155°C | [Boiling point ]
400.3±37.0 °C(Predicted) | [density ]
1.28±0.1 g/cm3(Predicted) | [storage temp. ]
Keep Cold | [solubility ]
DMSO (Slightly), Methanol (Slightly) | [form ]
Powder | [pka]
4.61±0.30(Predicted) | [color ]
Light pink or orange to light brown | [Detection Methods]
T,NMR | [BRN ]
8764547 | [InChI]
InChI=1S/C9H8BNO2/c12-10(13)8-5-7-3-1-2-4-9(7)11-6-8/h1-6,12-13H | [InChIKey]
YGDICLRMNDWZAK-UHFFFAOYSA-N | [SMILES]
N1C2C(=CC=CC=2)C=C(B(O)O)C=1 | [CAS DataBase Reference]
191162-39-7(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin .
R22:Harmful if swallowed. | [Safety Statements ]
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S22:Do not breathe dust .
S37:Wear suitable gloves .
S36:Wear suitable protective clothing . | [WGK Germany ]
3 | [Hazard Note ]
Irritant | [HazardClass ]
IRRITANT, KEEP COLD | [HS Code ]
29334900 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Chemical Properties]
light pink or orange to light brown powder | [Uses]
3-Quinolineboronic acid can be used as a reactant for: Preparation of P1-substituted symmetry-based human immunodeficiency virus protease inhibitors with antiviral activity against drug-resistant viruses Preparation of heterobiaryls via Suzuki-Miyaura cross-coupling with heteroaryl halides in co
| [Uses]
May contain varying amounts of anhydride. | [General Description]
May contain varying amounts of anhydride | [Synthesis]
General procedure for the synthesis of quinoline-3-boronic acid from 3-bromoquinoline: triisopropyl borate (3.30 mL, 29.06 mmol) and 3-bromoquinoline (3.00 g, 14.49 mmol) were added to a 250 mL two-necked round-bottomed flask under nitrogen protection and dissolved in anhydrous tetrahydrofuran (100 mL). The reaction system was cooled to -78 °C and a 2M hexane solution of n-butyllithium (14.50 mL, 29.00 mmol) was slowly added dropwise through a dropping funnel over a controlled period of 1 hour. After the dropwise addition, the reaction was kept at -78 °C for 2 hours. Subsequently, the acetone/dry ice bath was removed and the reaction system was slowly warmed to 0 °C. The reaction was quenched with 2 M hydrochloric acid solution, followed by adjusting the pH with 2 M sodium bicarbonate solution to 7. The reaction mixture was extracted with ethyl acetate (3 x 100 mL). The organic phases were combined, dried over anhydrous magnesium sulfate and concentrated to dryness under reduced pressure. The product was precipitated by addition of hexane to give a white solid in 80% yield. | [References]
[1] Dyes and Pigments, 2013, vol. 99, # 1, p. 105 - 115
[2] Synthetic Communications, 2003, vol. 33, # 5, p. 795 - 800
[3] Journal of Organic Chemistry, 2002, vol. 67, # 15, p. 5394 - 5397
[4] Patent: US2009/181941, 2009, A1. Location in patent: Page/Page column 49-50
[5] Journal of the American Chemical Society, 2012, vol. 134, # 28, p. 11667 - 11673 |
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