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417599

Sigma-Aldrich

4-Methoxyphenylboronic acid

≥95.0%

Synonym(s):

(4-Methoxyphenyl)boric acid, (p-Methoxyphenyl)boronic acid, 4-Anisylboronic acid, 4-Methoxybenzeneboronic acid, p-Anisylboronic acid, p-Methoxybenzeneboronic acid

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About This Item

Linear Formula:
CH3OC6H4B(OH)2
CAS Number:
5720-07-0
Molecular Weight:
151.96
Beilstein/REAXYS Number:
2936912
MDL number:
MFCD00039139
UNSPSC Code:
12352103
PubChem Substance ID:
24866163
NACRES:
NA.22

assay

≥95.0%

form

powder

mp

204-206 °C (lit.)

SMILES string

COc1ccc(cc1)B(O)O

InChI

1S/C7H9BO3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5,9-10H,1H3

InChI key

VOAAEKKFGLPLLU-UHFFFAOYSA-N

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Application

Reagent used for
  • Suzuki-Miyaura cross-coupling reactions
  • Pd-catalyzed direct arylation
  • Highly effective synthesis using palladium-catalyzed arylation Suzuki-Miyaura cross-coupling in water
  • Palladium-catalyzed stereoselective Heck-type reaction
  • Tandem-type Pd(II)-catalyzed oxidative Heck reaction and intramolecular C-H amidation sequence
  • Copper-mediated ligandless aerobic fluoroalkylation of arylboronic acids with fluoroalkyl iodides
  • Ruthenium catalyzed direct arylation
  • Rh-catalyzed asymmetric conjugate addition
  • Ligand-free copper-catalyzed coupling

Reagent used in Preparation of
  • Palladium(II) thiocarboxamide complexes as Suzuki coupling catalyst
  • Push-pull arylvinyldiazine chromophores with photophysical properties

Other Notes

Contains varying amounts of anhydride

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Mikhail Y Vorona et al.
Materials (Basel, Switzerland), 12(17) (2019-08-29)
Anthracene-based semiconductors are a class of molecules that have attracted interest due to their air stability, planarity, potential for strong intermolecular interactions, and favorable frontier molecular orbital energy levels. In this study seven novel 9,10-anthracene-based molecules were synthesized and their
Kosuke Ishijima et al.
Dalton transactions (Cambridge, England : 2003), 49(44), 15612-15621 (2020-09-24)
Benzo[b]arsole derivatives, being arsenic analogues of indole, were synthesized by utilizing a safely prepared arsenic precursor. The structural and photophysical properties of the obtained 2-arylbenzo[b]arsoles were experimentally and computationally studied in comparison with those of 1,2,5-triarylarsoles and 9-phenylarsafluorene. It was
Maria Makrinich et al.
Solid state nuclear magnetic resonance, 84, 196-203 (2017-05-06)
The ability of various pulse types, which are commonly applied for distance measurements, to saturate or invert quadrupolar spin polarization has been compared by observing their effect on magnetization recovery curves under magic-angle spinning. A selective central transition inversion pulse
M Lakshmi Kantam et al.
The Journal of organic chemistry, 71(25), 9522-9524 (2006-12-02)
N-Arylation of imidazoles and amines with arylboronic acids was accomplished with copper-exchanged fluorapatite (CuFAP) in methanol at room temperature. The products N-arylimidazoles and N-arylamines were isolated in good to excellent yields. A variety of arylboronic acids were converted to the
Palladium-Catalyzed Heck-Type Reactions of Allylic Esters with Arylboronic Acids or Potassium Aryltrifluoroborates
Yao, B.; et al.
Advanced Synthesis & Catalysis, 354, 1069-1076 (2012)
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