(4-chlorophenyl)boronic acid

• ChemBase ID: 8352
• Molecular Formular: C6H6BClO2
• Molecular Mass: 156.37464
• Monoisotopic Mass: 156.01493751
• SMILES: OB(O)c1ccc(cc1)Cl
• Canonical SMILES: OB(c1ccc(cc1)Cl)O
• InChI: InChI=1S/C6H6BClO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• InChIKey: CAYQIZIAYYNFCS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-chlorophenyl)boronic acid
• IUPAC Traditional name: benzeneboronic acid, p-chloro-
• Synonyms: 4-Chlorobenzeneboronic acid; (p-Chlorophenyl)boronic acid; NSC 25408; p-Chlorobenzeneboronic acid; 4-Chlorobenzeneboronic acid; 4-Chlorophenylboronic acid; 4-Chlorophenylboronic acid; (4-chlorophenyl)boronic acid; 4-Chlorophenylboronic acid; 4-Chlorobenzeneboronic acid; 4-氯苯硼酸; 4-氯苯基硼酸; 4-氯苯硼酸

Database IDs

• CAS Number: 1679-18-1
• EC Number: 216-845-5
• MDL Number: MFCD00039137
• Beilstein Number: 2936346
• PubChem SID: 24866159; 160971659
• PubChem CID: 74299

CALCULATED PROPERTIES

• Acid pKa: 8.731473
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.1575465
• LogD (pH = 7.4): 2.1381185
• Log P: 2.1578
• Molar Refractivity: 35.4083 cm^3
• Polarizability: 15.419235 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 262-264°C; 268-277°C; 284-289 °C(lit.); 284-289°C

Safety Information

• Storage Warning: Harmful/Irritant/Store under Argon/Keep Cold; IRRITANT
• RTECS: CY8950000
• 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: 95%; 97%; 98%; 98+%
• Linear Formula: ClC6H4B(OH)2

DETAILS

Sigma Aldrich - 417548

Other Notes
Contains a varying amounts of anhydride
Packaging
1, 10 g in glass bottle
25 g in poly bottle
Application
Reagent used for
• Palladium-catalyzed direct arylation1
• Cyclopalladation2
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation3
• Copper-mediated ligandless aerobic fluoroalkylation4
• Pd-catalyzed arylative cyclization5
• Ruthenium catalyzed direct arylation6
• Ligand-free copper-catalyzed coupling reactions7
• Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions8 Reagent used in Preparation of
• Catalysts for Suzuki-Miyaura cross-coupling2
• Palladium(II) thiocarboxamide complexes as Suzuki coupling catalysts9
• Biaryls by Suzuki reactions of aryl chlorides, bromides, and iodides with arylboronic acids10

REFERENCES

• GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979). See also Appendix 5.