8-Quinolinylboronic Acid
Product Information
Molecular Formula
C9H8NO2B
Molecular Weight
172.98
Description
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.
Synonyms
8-quinolinylboronic acid; quinolin-8-ylboronic acid
IUPAC Name
quinolin-8-ylboronic acid
SMILES
B(C1=C2C(=CC=C1)C=CC=N2)(O)O
InChI
InChI=1S/C9H8BNO2/c12-10(13)8-5-1-3-7-4-2-6-11-9(7)8/h1-6,12-13H
InChI Key
KXJJSKYICDAICD-UHFFFAOYSA-N
Boiling Point
400.3 °C at 760 mmHg
Melting Point
>300 °C (lit.)
Flash Point
Not applicable
Density
1.28 g/cm3
LogP
-0.08540
Safety Information
Hazards
H315 - H319 - H335
Precautionary Statement
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501
Signal Word
Warning
Computed Properties
Hydrogen Bond Donor Count
2
Hydrogen Bond Acceptor Count
3
Rotatable Bond Count
1
Exact Mass
173.0648087 g/mol
Monoisotopic Mass
173.0648087 g/mol
Topological Polar Surface Area
53.4Ų
Heavy Atom Count
13
Formal Charge
0
Complexity
177
Isotope Atom Count
0
Defined Atom Stereocenter Count
0
Undefined Atom Stereocenter Count
0
Defined Bond Stereocenter Count
0
Undefined Bond Stereocenter Count
0
Covalently-Bonded Unit Count
1
Compound Is Canonicalized
Yes
Patents
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-112778272-A | 2, 2' -biazaaryl ring bidentate ligand and preparation method and application thereof | 2021-02-02 |
| WO-2022047230-A1 | Compounds, compositions and methods for histone lysine demethylase inhibition | 2020-08-28 |
| CN-114075195-A | Pyrimidone derivatives and their use in medicine | 2020-08-21 |
| WO-2022037560-A1 | Pyrimidone derivative and application thereof in drug | 2020-08-21 |
| WO-2022032222-A1 | Compositions and methods for the treatment and diagnosis of cancer | 2020-08-07 |
| WO-2022032223-A1 | Compositions and methods for the treatment and diagnosis of cancer | 2020-08-07 |
| WO-2022032224-A1 | Compositions and methods for the treatment and diagnosis of cancer | 2020-08-07 |
| US-2022033417-A1 | Therapeutic agents and uses thereof | 2020-07-21 |
| WO-2022019892-A1 | Therapeutic agents and uses thereof | 2020-07-21 |
| KR-20220008636-A | Organic light-emitting compound and organic electroluminescent device using the same | 2020-07-14 |
Literatures
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 20967328 | 2010-12-07 | Reactivity of the bifunctional ambiphilic molecule 8-(dimesitylboryl)quinoline: hydrolysis and coordination to Cu(I), Ag(I) and Pd(II) | Dalton transactions (Cambridge, England : 2003) |
| 20452816 | 2010-09-01 | Determination of trace alkaline phosphatase by affinity adsorption solid substrate room temperature phosphorimetry based on wheat germ agglutinin labeled with 8-quinolineboronic acid phosphorescent molecular switch and prediction of diseases | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy |
| 20206009 | 2010-03-24 | 8-Quinolineboronic acid as a potential phosphorescent molecular switch for the determination of alpha-fetoprotein variant for the prediction of primary hepatocellular carcinoma | Analytica chimica acta |
| 19371087 | 2009-06-16 | Synthesis of aminoboronic acids and their applications in bifunctional catalysis | Accounts of chemical research |
| 12643902 | 2003-03-24 | A novel type of fluorescent boronic acid that shows large fluorescence intensity changes upon binding with a carbohydrate in aqueous solution at physiological pH | Bioorganic & medicinal chemistry letters |
