(4-methylphenyl)boronic acid

• ChemBase ID: 9649
• Molecular Formular: C7H9BO2
• Molecular Mass: 135.95616
• Monoisotopic Mass: 136.06955993
• SMILES: OB(O)c1ccc(cc1)C
• Canonical SMILES: OB(c1ccc(cc1)C)O
• InChI: InChI=1S/C7H9BO2/c1-6-2-4-7(5-3-6)8(9)10/h2-5,9-10H,1H3
• InChIKey: BIWQNIMLAISTBV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-methylphenyl)boronic acid
• IUPAC Traditional name: p-tolueneboronic acid
• Synonyms: (4-methylphenyl)boronic acid; (p-Methylphenyl)boronic acid; 4-Methylbenzeneboronic acid; 4-Tolueneboronic acid; NSC 62870; p-Methylbenzeneboronic acid; 4-Methylphenylboronic acid; p-Tolueneboronic acid; p-Tolylboronic acid; 4-Tolylboronic acid; 4-Tolylboronic acid; 4-Methylbenzeneboronic acid; 4-Metylphenylboronic acid; p-Tolylboronic acid; 4-Methylbenzeneboronic acid; 4-Tolylboronic acid; 4-METHYLPHENYLBORONIC ACID; (4-methylphenyl)boranediol; 4-甲基苯基硼酸; 4-甲苯硼酸; 对甲基苯硼酸; 4-甲基苯硼酸

Database IDs

• CAS Number: 5720/5/8; 5720-05-8
• MDL Number: MFCD00039138
• Beilstein Number: 2935970
• PubChem SID: 160972956; 24888998; 24864529
• PubChem CID: 79799

CALCULATED PROPERTIES

• Acid pKa: 8.860393
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.1068118
• LogD (pH = 7.4): 2.0922892
• Log P: 2.107
• Molar Refractivity: 35.6447 cm^3
• Polarizability: 15.298302 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: ~250 °C (dec. after the formation of the anhydride); 246-254°C; 248-250°C; 256-263 °C(lit.); 256-263°C; 262 - 263°C
• Hydrophobicity(logP): 2.094

Safety Information

• Storage Warning: IRRITANT; Irritant/Store under Argon/Keep Cold
• RTECS: XS7400000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36; 26-37
• 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: ≥98.0% (HPLC); 95%; 97%; 98%
• Grade: purum
• Linear Formula: CH3C6H4B(OH)2

DETAILS

Sigma Aldrich - 393622

Packaging
1, 10 g in glass bottle
Application
Reagent used for
• Palladium (Pd)-catalyzed direct arylation1
• Direct Palladium(II)-Catalyzed Synthesis2
• Palladium-catalyzed arylation by Suzuki-Miyaura cross-coupling in water3
• Cyclopalladation4
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence5
• Ruthenium catalyzed direct arylation6
• Rhodium-catalyzed asymmetric conjugate addition7
• Ligand-free copper-catalyzed cross-coupling reactions8
• Regioselective arylation and alkynylation by Suzuki-Miyaura and Sonogashira cross-coupling reactions9
• Ligand-free Suzuki, Sonogashira, and Heck cross-coupling reactions10Reagent used in Preparation of
• Catalysts for Suzuki-Miyaura cross-coupling of aryl bromides4
• Recyclable Palladium nanoparticle catalysts immobilized by click ionic copolymers as for Suzuki-Miyaura cross-coupling reactions in water11

REFERENCES

• GC reagent for diols: J. Chromat., 158, 33 (1978); 186, 307 (1979).
• For general chemistry of boronic acids, see Appendix 5.