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471933

Sigma-Aldrich

4-Iodophenylboronic acid

≥95.0%

Synonym(s):

B-(4-iodophenyl)-boronic acid, p-Iodophenylboronic acid, p-iodo-benzeneboronic acid

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About This Item

Linear Formula:
IC6H4B(OH)2
CAS Number:
5122-99-6
Molecular Weight:
247.83
MDL number:
MFCD01319014
UNSPSC Code:
12352103
PubChem Substance ID:
24870773
NACRES:
NA.22

Quality Level

200

assay

≥95.0%

mp

326-330 °C (lit.)

SMILES string

OB(O)c1ccc(I)cc1

InChI

1S/C6H6BIO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H

InChI key

PELJYVULHLKXFF-UHFFFAOYSA-N

Application

Reagent used for
  • Copper-mediated ligandless aerobic fluoroalkylation
  • Palladium-catalyzed aerobic oxidative cross-coupling reactions
  • Recyclable magnetic-nanoparticle-supported palladium catalyst for the Suzuki coupling reactions
  • Oxidative hydroxylation using a copper (Cu) catalyst
  • Ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling
  • Homocoupling using gold salts as a catalyst
  • Ruthenium (Ru)-catalyzed cross-coupling
  • CuI-catalyzed Suzuki coupling reactions
  • Palladium-catalyzed domino Heck-Mizoroki/Suzuki-Miyaura reactions
  • Manganese triacetate-mediated radical additions of arylboronic acids to alkenes

Reagent used in Preparation of
  • Pleuromutilin derivatives for ribosomal binding and antibacterial activity via "Click Chemistry"
  • Liquid crystalline polyacetylene derivatives

Other Notes

Contains varying amounts of anhydride

Pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - 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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Arne Dickschat et al.
Organic letters, 12(18), 3972-3974 (2010-08-20)
Arylboronic acids are shown to be valuable precursors for aryl radicals upon treatment with manganese triacetate. Under these oxidative conditions the intermediately generated aryl radicals undergo addition to olefins to give the arylhydroxylation products A in the presence of dioxygen.
Homocoupling of arylboronic acids catalyzed by simple gold salts
Matsuda, T.; et al.
Tetrahedron, 52, 4779-4781 (2011)
Samir Yahiaoui et al.
The Journal of organic chemistry, 76(8), 2433-2438 (2011-03-23)
A palladium(II)-catalyzed Heck-Mizoroki/Suzuki-Miyaura domino reaction involving metal coordinating dimethylaminoethyl vinyl ethers and a number of electron-rich and electron-deficient arylboronic acids has been developed. Through variation of the temperature and the concentration of the p-benzoquinone (p-Bq) ligand/reoxidant, conditions for the robust
Hong Li et al.
Chemical communications (Cambridge, England), 47(27), 7880-7882 (2011-06-11)
The first ruthenium-catalyzed cross-coupling of aldehydes with arylboronic acids is reported. Various aliphatic and aromatic aldehydes are transformed to the corresponding arylketones. A total of 31 examples with moderate to excellent yields are presented, together with the results of an
CuI-catalyzed Suzuki coupling reaction of organoboronic acids with alkynyl bromides
S. Wang, et al.,
Tetrahedron, 67, 4800-4806 (2011)
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