(3-chlorophenyl)boronic acid

• ChemBase ID: 8351
• Molecular Formular: C6H6BClO2
• Molecular Mass: 156.37464
• Monoisotopic Mass: 156.01493751
• SMILES: B(c1cccc(c1)Cl)(O)O
• Canonical SMILES: Clc1cccc(c1)B(O)O
• InChI: InChI=1S/C6H6BClO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H
• InChIKey: SDEAGACSNFSZCU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-chlorophenyl)boronic acid
• IUPAC Traditional name: 3-chlorophenylboronic acid
• Synonyms: 3-Chloro benzene boronic acid; (m-Chlorophenyl)boronic acid; 3-Chlorobenzeneboronic acid; m-Chlorobenzeneboronic acid; 3-Chlorophenylboronic acid; 3-Chlorobenzeneboronic acid; 3-Chlorophenylboronic acid; 3-Chlorobenzeneboronic acid; 3-Chlorophenylboronic acid; 3-氯苯基硼酸; 3-氯苯硼酸

Database IDs

• CAS Number: 63503-60-6
• EC Number: 000-000-0
• MDL Number: MFCD00161354
• Beilstein Number: 2936343
• PubChem SID: 24866158; 160971658
• PubChem CID: 2734323

CALCULATED PROPERTIES

• Acid pKa: 8.653718
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.157497
• LogD (pH = 7.4): 2.134362
• Log P: 2.1578
• Molar Refractivity: 35.4083 cm^3
• Polarizability: 15.412833 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 180-185°C; 185-189 °C(lit.); 185-189°C

Safety Information

• Storage Warning: IRRITANT; Irritant
• European Hazard Symbols: Irritant (Xi); Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22; 36/37/38
• Safety Statements: 26-37; 36
• TSCA Listed: false; 否
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332; H315-H319-H335
• GHS Precautionary statements: P261-P305+P351+P338-P302+P352-P321-P405-P501A; P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: 97%; 98%
• Linear Formula: ClC6H4B(OH)2

DETAILS

Sigma Aldrich - 417521

Other Notes
Contains varying amounts of anhydride
Packaging
1, 10 g in glass bottle
Application
Reactant involved in:
• 1,4-conjugate addition reactions with ethenesulfonamides to form arylethanesulfonamides1
• Suzuki-Miyaura reactions with dibromotrifluoromethylbenzene2
• Cross-coupling reactions with diazoesters3 or potassium cyanate4
• Synthesis of biarylketones and phthalides5
• Synthesis of inhibitors including PDE4 inhibitors6 among others