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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

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

Signal Word

Warning

Hazard Statements

H302,H315,H319,H335

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
An efficient and recyclable magnetic-nanoparticle-supported palladium catalyst for the Suzuki coupling reactions of organoboronic acids with alkynyl bromides
X. Zhang, et al.,
Synthesis, 18, 2975-2983 (2011)
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
Kazuhiko Tsukagoshi et al.
Journal of chromatography. A, 1123(1), 106-112 (2006-05-24)
Molecular recognition of mono- and disaccharides was performed making use of the interaction between their diol groups and p-iodophenylboronic acid in capillary electrophoresis (CE) with a chemiluminescence (CL) detection system. p-Iodophenylboronic acid acted as an enhancer for luminol-horseradish peroxidase-hydrogen peroxide
Disubstituted Liquid Crystalline Polyacetylene Derivatives That Exhibit Linearly Polarized Blue and Green Emissions
San Jose, B. A.; et al.
Macromolecules, 44, 6288-6302 (2011)
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