(2,4-dichlorophenyl)boronic acid

• ChemBase ID: 32595
• Molecular Formular: C6H5BCl2O2
• Molecular Mass: 190.8197
• Monoisotopic Mass: 189.97596516
• SMILES: c1(c(cc(cc1)Cl)Cl)B(O)O
• Canonical SMILES: Clc1ccc(c(c1)Cl)B(O)O
• InChI: InChI=1S/C6H5BCl2O2/c8-4-1-2-5(7(10)11)6(9)3-4/h1-3,10-11H
• InChIKey: QNEGDGPAXKYZHZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2,4-dichlorophenyl)boronic acid
• IUPAC Traditional name: 2,4-dichlorophenylboronic acid
• Synonyms: 2,4-Dichlorophenylboronic acid; 2,4-Dichlorobenzeneboronic acid; 2,4-Dichlorobenzeneboronic acid; 2,4-Dichlorophenylboronic acid; 2,4-Dichlorophenylboronic acid; 2,4-Dichlorobenzeneboron dihydroxide; 2,4-Dichlorobenzeneboronic acid; (2,4-dichlorophenyl)boranediol; 2,4-二氯苯基硼酸; 2,4-二氯苯硼酸

Database IDs

• CAS Number: 68716-47-2
• EC Number: 000-000-0
• MDL Number: MFCD00013930
• Beilstein Number: 4983878
• PubChem SID: 24874203; 160995902
• PubChem CID: 2734659

CALCULATED PROPERTIES

• Acid pKa: 8.388575
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6752422
• LogD (pH = 7.4): 2.633571
• Log P: 2.6758
• Molar Refractivity: 40.2131 cm^3
• Polarizability: 17.361109 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 242-245 deg. C; 242-245°C; 246-249 °C(lit.); 246-249°C
• Hydrophobicity(logP): 3.021

Safety Information

• Storage Warning: IRRITANT, KEEP COLD; Irritant/Keep Cold/Store under Argon
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-37
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 95%; 98%; 98+%
• Linear Formula: Cl2C6H3B(OH)2

DETAILS

Sigma Aldrich - 521388

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Reactant involved in:
• Suzuki coupling reactions with alkynyl bromides1,2 or aniline / thiophenol 3
• Selective hydroxylation to phenols4Reactant involved in synthesis of biologically active molecules including:
• N-hydroxyindole-2-carboxylates for use as lactate dehydrogenase inhibitors5
• Non-ATP competitive MK2 inhibitors6