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CAS

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8-Quinolineboronic acid is an organic compound with the chemical formula C9H8BNO2. It is a derivative of quinoline, a heterocyclic aromatic compound, and features a boronic acid functional group. 8-Quinolineboronic acid is known for its reactivity and stability, making it a versatile building block in organic synthesis.

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  • 86-58-8 Structure
  • Basic information

    1. Product Name: 8-Quinolineboronic acid
    2. Synonyms: 8-QUINOLINEBORONIC ACID;8-QUINOLINEBORONIC ACID, DIMER;8-QUINOLINYLBORONIC ACID;QUINOLINE-8-BORONIC ACID;QUINOLIN-8-YLBORONIC ACID;TIMTEC-BB SBB003824;RARECHEM AH PB 0127;8-QUINOLINEBORONIC ACID 95%
    3. CAS NO:86-58-8
    4. Molecular Formula: C9H8BNO2
    5. Molecular Weight: 172.98
    6. EINECS: -0
    7. Product Categories: blocks;BoronicAcids;Heterocycles;Boronic acids;Boronic Acid;Organoborons;Quinoline;Quinolines;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;OLED materials,pharm chemical,electronic;Boric Acid| Boric Acid Ester| Potassium Trifluoroborate
    8. Mol File: 86-58-8.mol
  • Chemical Properties

    1. Melting Point: >300 °C(lit.)
    2. Boiling Point: 160-165°C
    3. Flash Point: 195.871 °C
    4. Appearance: Yellow to beige/Powder
    5. Density: 1.289 g/cm3
    6. Refractive Index: N/A
    7. Storage Temp.: 0-6°C
    8. Solubility: soluble in Methanol
    9. PKA: 4.61±0.30(Predicted)
    10. Merck: 14,8069
    11. BRN: 147522
    12. CAS DataBase Reference: 8-Quinolineboronic acid(CAS DataBase Reference)
    13. NIST Chemistry Reference: 8-Quinolineboronic acid(86-58-8)
    14. EPA Substance Registry System: 8-Quinolineboronic acid(86-58-8)
  • Safety Data

    1. Hazard Codes: Xi
    2. Statements: 36/37/38-36/38
    3. Safety Statements: 26-37/39-36
    4. WGK Germany: 3
    5. RTECS:
    6. HazardClass: IRRITANT
    7. PackingGroup: N/A
    8. Hazardous Substances Data: 86-58-8(Hazardous Substances Data)

86-58-8 Usage

Uses

Used in Suzuki Reaction:
8-Quinolineboronic acid is used as a reactant in Suzuki reactions for the formation of C-C bonds between aryl and vinyl halides or triflates and arylboronic acids. This palladium-catalyzed cross-coupling reaction is widely employed in the synthesis of various organic compounds, including pharmaceuticals and natural products.
Used in C-H and C-S Bond Activations:
8-Quinolineboronic acid is used as a reactant involved in C-H and C-S bond activations, enabling the functionalization of unactivated carbon-hydrogen and carbon-sulfur bonds. This allows for the synthesis of diverse quinoline-containing compounds with potential applications in medicinal chemistry and materials science.
Used in Synthesis of Pyridazine:
8-Quinolineboronic acid is used as a building block in the synthesis of pyridazine via sequential amination, Suzuki coupling, and alkylation reactions. Pyridazine is a fused bicyclic compound with potential applications as a pharmaceutical intermediate and in the development of novel agrochemicals.
Used in Synthesis of Biaryl Monophosphorus Ligands:
8-Quinolineboronic acid is used as a reactant in Suzuki-Miyaura coupling reactions for the synthesis of biaryl monophosphorus ligands. These ligands are valuable in asymmetric catalysis, enabling the enantioselective synthesis of chiral compounds with potential applications in the pharmaceutical industry.
Used in Synthesis of Fused Tricyclic Oxa-Quinolones:
8-Quinolineboronic acid is used as a reactant in the synthesis of fused tricyclic oxa-quinolones, which are structurally diverse and exhibit a range of biological activities. These compounds have potential applications as anticancer agents, antimalarials, and antitubercular drugs.
Used in Synthesis of Substituted β-Amino Acids:
8-Quinolineboronic acid is used as a building block in the synthesis of substituted β-amino acids via Suzuki-Miyaura coupling reactions. These non-natural amino acids are valuable in the development of peptidomimetics, which can serve as bioactive molecules with potential applications in drug discovery.
Used in Copper-Catalyzed Azidation:
8-Quinolineboronic acid is used as a reactant in copper-catalyzed azidation with sodium azide, enabling the introduction of azide groups into organic molecules. This reaction can be used for the synthesis of various functionalized compounds, including those with potential applications in click chemistry.
Used in Studies of Fluoride Effects on Boronic Acid Stability:
8-Quinolineboronic acid is used as a model compound in studies investigating the effects of fluoride on the stability of boronic acids during click reactions. Understanding these effects can help optimize reaction conditions and improve the efficiency of click chemistry processes.

Check Digit Verification of cas no

The CAS Registry Mumber 86-58-8 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 6 respectively; the second part has 2 digits, 5 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 86-58:
(4*8)+(3*6)+(2*5)+(1*8)=68
68 % 10 = 8
So 86-58-8 is a valid CAS Registry Number.

86-58-8 Well-known Company Product Price

  • Brand
  • (Code)Product description
  • CAS number
  • Packaging
  • Price
  • Detail
  • Alfa Aesar

  • (L19640)  Quinoline-8-boronic acid, 99%   

  • 86-58-8

  • 250mg

  • 763.0CNY

  • Detail
  • Alfa Aesar

  • (L19640)  Quinoline-8-boronic acid, 99%   

  • 86-58-8

  • 1g

  • 2121.0CNY

  • Detail
  • Aldrich

  • (542865)  8-Quinolinylboronicacid  technical grade

  • 86-58-8

  • 542865-250MG

  • 656.37CNY

  • Detail
  • Aldrich

  • (542865)  8-Quinolinylboronicacid  technical grade

  • 86-58-8

  • 542865-1G

  • 1,623.96CNY

  • Detail

86-58-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name 8-Quinolinylboronic acid

1.2 Other means of identification

Product number -
Other names Quinoline-8-boronic acid

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:86-58-8 SDS

86-58-8Related news

Determination of trace alkaline phosphatase by affinity adsorption solid substrate room temperature phosphorimetry based on wheat germ agglutinin labeled with 8-Quinolineboronic acid (cas 86-58-8) phosphorescent molecular switch and prediction of diseases07/16/2019

The 8-quinolineboronic acid phosphorescent molecular switch (abbreviated as PMS-8-QBA. Thereinto, 8-QBA is 8-quinolineboronic acid, and PMS is phosphorescent molecular switch) was found for the first time. PMS-8-QBA, which was in the “off” state, could only emit weak room temperature phosphore...detailed

8-Quinolineboronic acid (cas 86-58-8) as a potential phosphorescent molecular switch for the determination of alpha-fetoprotein variant for the prediction of primary hepatocellular carcinoma07/15/2019

8-Quinolineboronic acid phosphorescent molecular switch (8-QBA-PMS) in the “off” state emitted weak room temperature phosphorescence (RTP) of 8-QBA on the acetylcellulose membrane (ACM) with the perturbation of Pb2+. When 8-QBA-PMS was used to label concanavalin agglutinin (Con A) to form 8-QB...detailed

86-58-8Relevant articles and documents

NOVEL PYRIDIN-2(1H)ONE DERIVATIVES, THEIR PREPARATION AND THEIR USE FOR THE TREATMENT OF PAIN

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Page/Page column 15; 23, (2021/04/10)

The present invention concerns novel pyridin-2(1H)one derivatives, their process of preparation and their use in therapeutics, in particular as agents for treating and/or preventing pain.

Silicon-bridged metallocene complex containing nitrogen heterocyclic ring structures and application thereof

-

Paragraph 0045-0048, (2020/06/04)

The invention relates to a preparation method and application of an olefin polymerization reaction catalyst, in particular to a silicon-bridged metallocene complex with nitrogen heterocyclic ring structures and application thereof. Molecules of the designed novel silicon-bridged metallocene complex contain three different nitrogen heterocyclic ring structures, and the distances from nitrogen atomsto a metal center are different, so that different chemical environments are provided for the metal center, and the metallocene complex with a novel structure is constructed. By changing a skeleton structure and a substituent group, the three-dimensional effect and the electronic effect of the metallocene complex can be conveniently regulated and controlled, the catalytic performance is regulatedand controlled, and polyolefin high polymer materials with different structures and properties are prepared.

Silicon-bridged metallocene complex with C2 symmetrical structure and application thereof

-

Paragraph 0037-0040, (2020/06/09)

The invention relates to a preparation method and application of an olefin polymerization reaction catalyst, in particular to a silicon-bridged metallocene complex with a C2 symmetrical structure andapplication thereof. Molecules of the silicon-bridged metallocene complex with the novel C2 symmetric structure in the invention contain seven different ligand structures, and ligands have chemical groups with different electron donating capacities, so different chemical environments are provided for a metal center, and the metallocene complex with the novel structure is constructed. By changing askeleton structure and substituent groups, the three-dimensional effect and the electronic effect of the metallocene complex can be conveniently regulated and controlled, so the catalytic performanceis regulated and controlled, and polyolefin high polymer materials with different structures and properties are prepared.

Pyridin-2(1H)one derivatives: A possible new class of therapeutics for mechanical allodynia

Abrunhosa-Thomas, Isabelle,Anizon, Fabrice,Artola, Alain,Dallel, Radhouane,Descheemaeker, Amélie,Giraud, Francis,Moreau, Pascale,Nauton, Lionel,Pinto-Pardo, Nicolas,Théry, Vincent,Visseq, Alexia

, (2019/12/24)

Mechanical Allodynia (MA), a frequent chronic pain symptom caused by innocuous stimuli, constitutes an unmet medical need, as treatments using analgesics available today are not always effective and can be associated with important side-effects. A series of 3,5-disubstituted pyridin-2(1H)-ones was designed, synthesized and evaluated in vivo toward a rat model of inflammatory MA. We found that the series rapidly and strongly prevented the development of MA. 3-(2-Bromophenyl)-5-(phenylamino)pyridin-2(1H)-one 69, the most active compound of the series, was also able to quickly reverse neuropathic MA in rats. Next, when 69 was evaluated toward a panel of 50 protein kinases (PK) in order to identify its potential biological target(s), we found that 69 is a p38α MAPK inhibitor, a PK known to contribute to pain hypersensitivity in animal models. 3,5-Disubstituted pyridin-2(1H)-ones thus could represent a novel class of analgesic for the treatment of MA.

COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME

-

Paragraph 0248; 0249, (2016/09/12)

A compound represented by Formula 1 or Formula 2, and an organic light-emitting device including a first electrode; a second electrode facing the first electrode; and an organic layer between the first electrode and the second electrode, the organic layer including an emission layer and the compound represented by Formula 1 or Formula 2.

COMPOUND FOR ORGANIC ELECTRONIC ELEMENT, ORGANIC ELECTRONIC ELEMENT USING THE SAME, AND AN ELECTRONIC DEVICE THEREOF

-

Paragraph 0157; 0166; 0168, (2016/10/07)

The present invention provides a novel compound capable of improving light emitting efficiency, stability and lifespan of an element, an organic electronic element using the same and an electronic device thereof.(110) Substrate(120) Positive electrode(130) Hole injection layer(140) Hole transfer layer(141) Buffer layer(150) Light emitting layer(151) Light-emitting assisting layer(160) Electron transfer layer(170) Electron injection layer(180) Negative electrodeCOPYRIGHT KIPO 2016

Investigation of a lithium-halogen exchange flow process for the preparation of boronates by using a cryo-flow reactor

Newby, James A.,Huck, Lena,Blaylock, D. Wayne,Witt, Paul M.,Ley, Steven V.,Browne, Duncan L.

, p. 263 - 271 (2014/01/17)

Conducting low-temperature organometallic reactions under continuous flow conditions offers the potential to more accurately control exotherms and thus provide more reproducible and scalable processes. Herein, progress towards this goal with regards to the lithium-halogen exchange/borylation reaction is reported. In addition to improving the scope of substrates available on a research scale, methods to improve reaction profiles and expedite purification of the products are also described. On moving to a continuous system, thermocouple measurements have been used to track exotherms and provide a level of safety for continuous processing of organometallic reagents. The use of an in-line continuous liquid-liquid separation device to circumvent labour intensive downstream off-line processing is also reported. A cool setup: A small footprint, modular setup based around a cryo-flow reactor is reported for the preparation of gram quantities of boronic esters. With minimum alteration, including the addition of a data logger with thermocouples and a liquid-liquid separator, the same equipment can be used to scale the process, inclusive of an in-line extraction. Copyright

Synthesis of functionalized porphyrins as oxygen ligand receptors

Wada, Kenji,Mizutani, Tadashi,Kitagawa, Susumu

, p. 5123 - 5131 (2007/10/03)

Oxophilic synthetic receptors were designed and synthesized using a porphyrin scaffold, with the aim of constructing a preorganized complementary binding site for phenols and carbohydrates. We pursued three strategies for phenol recognition: (1) Lewis aci

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