(quinolin-8-yl)boronic acid

• ChemBase ID: 8745
• Molecular Formular: C9H8BNO2
• Molecular Mass: 172.97632
• Monoisotopic Mass: 173.0648089
• SMILES: c1cc(c2c(c1)cccn2)B(O)O
• Canonical SMILES: OB(c1cccc2c1nccc2)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (quinolin-8-yl)boronic acid
• IUPAC Traditional name: 8-quinolineboronic acid
• Synonyms: Quinoline-8-boronic acid; 8-Boronoquinoline; Quinoline-8-boronic acid; 8-Quinolineboronic acid; 8-Quinolineboronic acid; 8-Quinolinylboronic acid; quinolin-8-ylboronic acid; 喹啉-8-硼酸; 喹啉-8-硼酸; 8-喹啉硼酸

Database IDs

• CAS Number: 662138-96-7; 86-58-8
• EC Number: 000-000-0
• MDL Number: MFCD01114698
• Beilstein Number: 147522
• Merck Index: 148069
• PubChem SID: 160972052; 24878641
• PubChem CID: 2734380

CALCULATED PROPERTIES

• Acid pKa: 8.332415
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.7236936
• LogD (pH = 7.4): 1.6813616
• Log P: 1.7292
• Molar Refractivity: 44.5248 cm^3
• Polarizability: 20.179743 Å^3
• Polar Surface Area: 53.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300 °C(lit.); >300°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26; 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338; P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%; 99%
• Grade: technical grade
• Empirical Formula (Hill Notation): C9H8BNO2

DETAILS

Apollo Scientific Ltd - OR4993

Exists as dimer.Note: NMR spectrum must be run in D2O.

Sigma Aldrich - 542865

Other Notes
Contains varying amounts of anhydride
Packaging
1 g in glass bottle
250 mg in glass bottle
Application
Reactant involved in:
• C-H and C-S bond activations1
• Synthesis of pyridazine via sequential amination / Suzuki coupling / alkylation reactions2
• Suzuki-Miyaura coupling reactions for synthesis of biaryl monophosphorus ligands3, fused tricyclic oxa-quinolones4, or substituted β-amino acids5
• Copper-catalyzed azidation with sodium azide6
• Studies of the affect of fluoride on the stability of boronic acids during click reactions7