(isoquinolin-4-yl)boronic acid

• ChemBase ID: 12414
• Molecular Formular: C9H8BNO2
• Molecular Mass: 172.97632
• Monoisotopic Mass: 173.0648089
• SMILES: c1ccc2c(c1)cncc2B(O)O
• Canonical SMILES: OB(c1cncc2c1cccc2)O
• InChI: InChI=1S/C9H8BNO2/c12-10(13)9-6-11-5-7-3-1-2-4-8(7)9/h1-6,12-13H
• InChIKey: GDTOUTKTCGPAGY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (isoquinolin-4-yl)boronic acid
• IUPAC Traditional name: isoquinolin-4-ylboronic acid
• Synonyms: Isoquinolin-4-ylboronic acid; Isoquinoline-4-boronic acid; 4-Isoquinolineboronic acid; Isoquinoline-4-boronic acid; Isoquinoline-4-boronic acid; 4-Boronoisoquinoline; 4-异喹啉硼酸; 异喹啉-4-硼酸; 异喹啉-4-硼酸

Database IDs

• CAS Number: 192182-56-2
• MDL Number: MFCD03412093
• PubChem SID: 160975721
• PubChem CID: 3761204

CALCULATED PROPERTIES

• Acid pKa: 8.288253
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3088982
• LogD (pH = 7.4): 1.2771883
• Log P: 1.3301
• Molar Refractivity: 44.8968 cm^3
• Polarizability: 20.17581 Å^3
• Polar Surface Area: 53.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >270°C; 230-234 °C

Safety Information

• Storage Warning: IRRITANT; Irritant/Moisture Sensitive/Keep Cold/Store under Argon
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C9H8BNO2

DETAILS

Sigma Aldrich - 707929

General description
May contain varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Preparation of selective steroid-11β-hydroxylase (CYP11B1) inhibitors for treatment of cortisol dependent diseases1
• Preparation of tetrabutylammonium trifluoroborates2
• Preparation of heteroaryl substituted tetrahydropyrroloijquinolinone derivatives as aldosterone synthase inhibitors3
• Synthesis of aminoarylpyridazines as selective CB2 agonists for treatment of inflammatory pain4
• Preparation of acyl substituted indoles via palladium-catalyzed domino coupling/carbonylation/Suzuki coupling of dibromoethenylanilines5
• Synthesis of antagonists of bacterial quorum sensing6
• Preparation of potassium heteroaryl trifluoroborates from boronic acids and their use as coupling partners with various aryl and heteroaryl halides in Suzuki-Miyaura cross-coupling reactions7