(3-chloro-4-methoxyphenyl)boronic acid

• ChemBase ID: 32789
• Molecular Formular: C7H8BClO3
• Molecular Mass: 186.40062
• Monoisotopic Mass: 186.0255022
• SMILES: c1(cc(c(cc1)OC)Cl)B(O)O
• Canonical SMILES: COc1ccc(cc1Cl)B(O)O
• InChI: InChI=1S/C7H8BClO3/c1-12-7-3-2-5(8(10)11)4-6(7)9/h2-4,10-11H,1H3
• InChIKey: VUTJHOWRPUPHIG-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-chloro-4-methoxyphenyl)boronic acid
• IUPAC Traditional name: 3-chloro-4-methoxyphenylboronic acid
• Synonyms: 3-Chloro-4-methoxyphenylboronic acid; 4-Borono-2-chloroanisole; 3-Chloro-4-methoxybenzeneboronic acid; 3-Chloro-4-methoxyphenylboronic acid; 3-氯-4-甲氧基苯硼酸

Database IDs

• CAS Number: 175883-60-0
• MDL Number: MFCD04039888
• PubChem SID: 24880182; 160996096
• PubChem CID: 3247522

CALCULATED PROPERTIES

• Acid pKa: 8.789376
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.9048783
• LogD (pH = 7.4): 1.8878272
• Log P: 1.9051
• Molar Refractivity: 41.8715 cm^3
• Polarizability: 17.977938 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 223-228°CC; 238-242 °C(lit.); 238-242°C

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold/Store under Argon; IRRITANT, KEEP COLD
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: 98%
• Linear Formula: ClC6H3(OCH3)B(OH)2

DETAILS

Sigma Aldrich - 564486

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5 g in glass bottle
Application
Reactant for:
• Iron-catalyzed oxidative coupling with benzene derivatives through homolytic aromatic substitution1
• Preparation of microtubule inhibitors as potential antitumors2
• Rhodium/chiral ligand-catalyzed arylation/Dieckmann-type annulation3
• Copper-catalyzed oxidative N-arylation4
• Suzuki and Stille palladium-catalyzed coupling5
• Boron-Heck arylation6