(2-methylphenyl)boronic acid

• ChemBase ID: 9647
• Molecular Formular: C7H9BO2
• Molecular Mass: 135.95616
• Monoisotopic Mass: 136.06955993
• SMILES: c1c(c(ccc1)B(O)O)C
• Canonical SMILES: OB(c1ccccc1C)O
• InChI: InChI=1S/C7H9BO2/c1-6-4-2-3-5-7(6)8(9)10/h2-5,9-10H,1H3
• InChIKey: NSJVYHOPHZMZPN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2-methylphenyl)boronic acid
• IUPAC Traditional name: 2-methylphenylboronic acid
• Synonyms: (2-Tolyl)boronic acid; 2-Methyl-1-phenylboronic acid; 2-Methylbenzeneboronic acid; 2-Tolueneboronic acid; o-Boronotoluene; o-Methylphenylboronic acid; o-Tolueneboronic acid; 2-Methylphenylboronic acid; o-Tolylboronic acid; 2-Tolylboronic acid; 2-Tolylboronic acid; 2-Methylbenzeneboronic acid; (2-methylphenyl)boranediol; o-Tolylboronic acid; 2-Methylbenzeneboronic acid; 2-Methylphenylboronic acid; 2-甲基苯硼酸; 邻甲基苯硼酸; 2-甲基苯硼酸

Database IDs

• CAS Number: 16419-60-6
• EC Number: 000-000-0
• MDL Number: MFCD00093526
• Beilstein Number: 2935796
• PubChem SID: 160972954; 24864527
• PubChem CID: 2733267

CALCULATED PROPERTIES

• Acid pKa: 8.825132
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.1067958
• LogD (pH = 7.4): 2.0910673
• Log P: 2.107
• Molar Refractivity: 35.6447 cm^3
• Polarizability: 15.298734 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 162-164 °C(lit.); 162-164°C; 163 - 164°C; ca 162-164°C
• Hydrophobicity(logP): 2.094

Safety Information

• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• RTECS: ED7777777
• 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: ≥95.0%; 95%; 98%
• Linear Formula: CH3C6H4B(OH)2

DETAILS

Sigma Aldrich - 393606

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5, 25 g in glass bottle
Application
Reagent used for
• Palladium-catalyzed direct arylation of pyrazoles with phenylboronic acids1
• Pd-catalyzed arylation using Suzuki-Miyaura cross-coupling in water2
• Ruthenium catalyzed direct arylation reactions3
• Ligand-free copper-catalyzed coupling reactions4
• Copper-catalyzed cross-coupling reactions of diaryl diselenides5
• Phosphine-free Suzuki-Miyaura cross-coupling reactions6
• Rhodium-catalyzed asymmetric 1,4-addition reactions7 Reagent used in Preparation of
• Chiral monophosphorus ligands in asymmetric Suzuki-Miyaura coupling reaction8
• Palladium nanoparticles immobilized by click ionic copolymers as recyclable catalysts for Suzuki-Miyaura cross-coupling reaction in water9
• Human farnesyl pyrophosphate synthase inhibitors as antitumor agents for multiple myeloma cells10

REFERENCES

• Conditions for ligand-free Suzuki cross-coupling of arylboronic acids with aryl iodides, catalyzed by Palladium(II) acetate, 10516, to give unsymmetrical biphenyls in high yield, are described: Org. Synth., 75, 61(1997). See Appendix 5.