(2-chloropyridin-3-yl)boronic acid

• ChemBase ID: 32692
• Molecular Formular: C5H5BClNO2
• Molecular Mass: 157.3627
• Monoisotopic Mass: 157.01018649
• SMILES: c1(c(cccn1)B(O)O)Cl
• Canonical SMILES: OB(c1cccnc1Cl)O
• InChI: InChI=1S/C5H5BClNO2/c7-5-4(6(9)10)2-1-3-8-5/h1-3,9-10H
• InChIKey: VRDAOVQZVXYRNH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-chloropyridin-3-yl)boronic acid
• IUPAC Traditional name: 2-chloropyridin-3-ylboronic acid
• Synonyms: 2-Chloropyridine-3-boronic acid; (2-Chloro-3-pyridyl)boronic acid; (2-Chloropyridin-3-yl)boronic acid; Dihydroxy(2-chloro-3-pyridyl)borane; 2-Chloropyridine-3-boronic acid; 2-Chloro-3-pyridylboronic acid; (2-chloropyridin-3-yl)boronic acid; 2-Chloropyridine-3-boronic acid 96%; 2-Chloro-3-pyridylboronic acid; 2-氯吡啶-3-硼酸

Database IDs

• CAS Number: 381248-04-0
• EC Number: 000-000-0
• MDL Number: MFCD03094997
• Beilstein Number: 9119913
• PubChem SID: 160995999
• PubChem CID: 2762704

CALCULATED PROPERTIES

• Acid pKa: 8.074363
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.2154486
• LogD (pH = 7.4): 1.133597
• Log P: 1.2166
• Molar Refractivity: 34.3127 cm^3
• Polarizability: 14.629703 Å^3
• Polar Surface Area: 53.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 121°C; 121-134 °C; 160 - 162°C; 160°C
• Hydrophobicity(logP): 0.895

Safety Information

• Storage Warning: IRRITANT; Irritant/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: 95%; 95+%; 96%; 98%
• Empirical Formula (Hill Notation): C5H5BClNO2

DETAILS

Sigma Aldrich - 697095

Frequently Asked Questions
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Application
May contain varying amounts of anhydride
Reactant for:
• Synthesis of Et canthinone-3-carboxylates from Et 4-bromo-6-methoxy-1,5-naphthyridine-3-carboxylate via a Pd-catalyzed Suzuki-Miyaura coupling and a Cu-catalyzed amidation reaction1
• Preparation of arylmethylpyrrolidinylmethanols and amine derivatives via reaction with MIDA followed by Suzuki reaction with halides or amination with amines2
• Preparation of arylazabicyclooctane derivatives as potential arginine vasopressin receptor antagonists3
• Regioselective preparation of halo-oligopyridines and oligopyridines by the Suzuki-Miyaura cross-coupling reaction4
Packaging
1 g in glass bottle
250 mg in glass bottle