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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:
Molecular Weight:
247.83
MDL number:
UNSPSC Code:
12352103
PubChem Substance ID:
NACRES:
NA.22

Quality Level

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

Signal Word

Warning

Hazard Statements

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
CuI-catalyzed Suzuki coupling reaction of organoboronic acids with alkynyl bromides
S. Wang, et al.,
Tetrahedron, 67, 4800-4806 (2011)
Disubstituted Liquid Crystalline Polyacetylene Derivatives That Exhibit Linearly Polarized Blue and Green Emissions
San Jose, B. A.; et al.
Macromolecules, 44, 6288-6302 (2011)
Kiyofumi Inamoto et al.
Chemical communications (Cambridge, England), 47(42), 11775-11777 (2011-10-01)
Copper-catalysed oxidative hydroxylation of arylboronic acids was accomplished in water containing an amphiphilic surfactant, providing facile access to phenol derivatives.
Alison M Berezuk et al.
Scientific reports, 8(1), 12933-12933 (2018-08-30)
In Escherichia coli, formation of new cells is mediated by the elongasome and divisome that govern cell elongation and septation, respectively. Proper transition between these events is essential to ensure viable progeny are produced; however, the components of each complex

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