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
Canonical 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
The molarity calculator equation

Mass (g) = Concentration (mol/L) × Volume (L) × Molecular Weight (g/mol)

The dilution calculator equation

Concentration (start) × Volume (start) = Concentration (final) × Volume (final)

This equation is commonly abbreviated as: C1V1 = C2V2

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