(3,4-dichlorophenyl)boronic acid

• ChemBase ID: 10574
• Molecular Formular: C6H5BCl2O2
• Molecular Mass: 190.8197
• Monoisotopic Mass: 189.97596516
• SMILES: c1c(c(cc(c1)B(O)O)Cl)Cl
• Canonical SMILES: OB(c1ccc(c(c1)Cl)Cl)O
• InChI: InChI=1S/C6H5BCl2O2/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3,10-11H
• InChIKey: JKIGHOARKAIPJI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3,4-dichlorophenyl)boronic acid
• IUPAC Traditional name: 3,4-dichlorophenylboronic acid
• Synonyms: 3,4-Dichlorobenzeneboronic acid; 3,4-Dichlorophenylboronic acid; 3,4-Dichlorobenzeneboronic acid; (3,4-dichlorophenyl)boranediol; 3,4-Dichlorophenylboronic acid; 3,4-Dichlorobenzeneboronic acid; 3,4-Dichlorophenylboronic acid; 3,4-二氯苯硼酸

Database IDs

• CAS Number: 151169-75-4
• EC Number: 000-000-0
• MDL Number: MFCD01074646
• Beilstein Number: 7369790
• PubChem SID: 160973881; 24870771
• PubChem CID: 2734330

CALCULATED PROPERTIES

• Acid pKa: 8.652279
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.6754959
• LogD (pH = 7.4): 2.652286
• Log P: 2.6758
• Molar Refractivity: 40.2131 cm^3
• Polarizability: 17.376898 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 270-274°C; 270-274°C; 280 - 285°C; 280-285 °C(lit.); 280-285°C
• Hydrophobicity(logP): 2.901

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under Argon/Keep Cold
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37-60
• 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: 95%; 97%; 98%
• Linear Formula: Cl2C6H3B(OH)2

DETAILS

Sigma Aldrich - 471917

Packaging
5, 25 g in glass bottle
Application
Reactant involved in:
• Lithiation/borylation-protodeboronation of homoallyl carbamates1
• Suzuki coupling reactions2,3Precursor / reactant involved in synthesis of biologically active molecules including:
• Mycobacterium tuberculosis H37Rv chorismate mutase inhibitors2
• Pyrrole derivatives as PDE4B inhibitors3
• Nitrovinyl biphenyls as anticancer agents4
• Dual immunosuppressive and anti-inflammatory agents5
• Pyrazolopyrimidines as Cryptosporidium and Toxoplasma CDPK1 inhibitors6