(4-methoxyphenyl)boronic acid

• ChemBase ID: 9450
• Molecular Formular: C7H9BO3
• Molecular Mass: 151.95556
• Monoisotopic Mass: 152.06447455
• SMILES: c1c(ccc(c1)B(O)O)OC
• Canonical SMILES: COc1ccc(cc1)B(O)O
• InChI: InChI=1S/C7H9BO3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3
• InChIKey: VOAAEKKFGLPLLU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-methoxyphenyl)boronic acid
• IUPAC Traditional name: 4-methoxyphenylboronic acid
• Synonyms: (4-Methoxyphenyl)boronic Acid; [4-(Methyloxy)phenyl]boronic Acid; 4-Methoxylphenylboronic Acid; (4-Methoxyphenyl)boric acid; (p-Methoxyphenyl)boronic acid; 4-Anisylboronic acid; p-Methoxybenzeneboronic acid; p-Anisylboronic acid; 4-Methoxybenzeneboronic acid; 4-Methoxyphenylboronic acid; 4-Methoxyphenylboronic acid; 4-Methoxyphenylboronic acid; 4-Methoxybenzeneboronic acid; (4-methoxyphenyl)boranediol; (4-methoxyphenyl)boronic acid; 4-Boronoanisole; 4-Methoxybenzeneboronic acid; 对甲氧基苯硼酸; 4-甲氧基苯硼酸

Database IDs

• CAS Number: 5720-07-0
• MDL Number: MFCD00039139
• Beilstein Number: 2936912
• PubChem SID: 24883853; 24866163; 160972757
• PubChem CID: 201262

CALCULATED PROPERTIES

• Acid pKa: 8.881573
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3869206
• LogD (pH = 7.4): 1.3730782
• Log P: 1.3871
• Molar Refractivity: 37.0667 cm^3
• Polarizability: 16.051516 Å^3
• Polar Surface Area: 49.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 202-208°C; 204-206 °C(lit.); 204-206°C; 205 - 206°C; 208-211°C; 209-212 °C
• Hydrophobicity(logP): 1.514

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT; Irritant/Keep Cold/Store under Argon
• RTECS: CY8975000
• 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% (TLC); ≥95.0%; 95%; 97%; 97+%; 98%
• Grade: technical
• Linear Formula: CH3OC6H4B(OH)2

DETAILS

Sigma Aldrich - 417599

Other Notes
Contains varying amounts of anhydride
Packaging
1, 5, 25 g in glass bottle
Application
Reagent used for
• Suzuki-Miyaura cross-coupling reactions1
• Pd-catalyzed direct arylation2
• Highly effective synthesis using palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water3
• Palladium-catalyzed stereoselective Heck-type reaction4
• Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence5
• Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides6
• Ruthenium catalyzed direct arylation7
• Rh-catalyzed asymmetric conjugate addition8
• Ligand-free copper-catalyzed coupling9 Reagent used in Preparation of
• Palladium(II) thiocarboxamide complexes as Suzuki coupling catalyst10
• Push-pull arylvinyldiazine chromophores with photophysical properties11

Sigma Aldrich - 65168

Other Notes
Contains varying amounts of anhydride

Toronto Research Chemicals - M260945

4-Methoxylphenylboronic Acid is a phenylboronic acid used to investigate boron function in plants.

REFERENCES

• Baldwin, T., et al.: Plant Physiol., 103, 115 (1993)
• Andeme-Onzighi, C., et al.: Planta, 215, 949 (1993)
• Brown, P., et al.: Plant Biol. 4, 205 (1993)
• GC reagent for diols: J. Chromat., 158, 33 (1978), 186, 307 (1979).
• For an illustrative example of the silver oxide promoted Suzuki coupling with sensitive ɑ-halo enones, under extremely mild conditions, see: Org. Synth., 75, 69 (1997):