(4-iodophenyl)boronic acid

• ChemBase ID: 8795
• Molecular Formular: C6H6BIO2
• Molecular Mass: 247.82611
• Monoisotopic Mass: 247.95055783
• SMILES: c1c(ccc(c1)B(O)O)I
• Canonical SMILES: OB(c1ccc(cc1)I)O
• InChI: InChI=1S/C6H6BIO2/c8-6-3-1-5(2-4-6)7(9)10/h1-4,9-10H
• InChIKey: PELJYVULHLKXFF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4-iodophenyl)boronic acid
• IUPAC Traditional name: 4-iodophenylboronic acid
• Synonyms: 4-Iodophenylboronic acid; (4-Iodophenyl)boronic acid; 4-Iodophenylboronic acid; 4-Iodobenzeneboronic acid; B-(4-iodophenyl)-boronic acid; p-iodo-benzeneboronic acid; p-Iodophenylboronic acid; 4-Iodophenylboronic acid; 4-Boronoiodobenzene; 4-Iodobenzeneboronic acid; 4-碘苯硼酸

Database IDs

• CAS Number: 5122-99-6
• MDL Number: MFCD02093073; MFCD01319014
• PubChem SID: 160972102; 24870773
• PubChem CID: 151254

CALCULATED PROPERTIES

• Acid pKa: 8.730529
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.630146
• LogD (pH = 7.4): 2.6106768
• Log P: 2.6304
• Molar Refractivity: 43.966 cm^3
• Polarizability: 18.743023 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 322-326°C; 326-330 °C(lit.)

Safety Information

• Storage Warning: Harmful/Irritant/Keep Cold; IRRITANT; Light Sensitive
• European Hazard Symbols: X; Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36; 26-36/37
• TSCA Listed: false; 否
• GHS Pictograms: GHS06; GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H301-H315-H319-H335; H302-H315-H319-H335
• GHS Precautionary statements: P261-P301+P310-P305+P351+P338-P302+P352-P405-P501A; P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0%; 97%; 98%
• Linear Formula: IC6H4B(OH)2

DETAILS

Sigma Aldrich - 471933

Other Notes
Contains varying amounts of anhydride
Packaging
5, 25 g in glass bottle
Application
Reagent used for
• Copper-mediated ligandless aerobic fluoroalkylation1
• Palladium-catalyzed aerobic oxidative cross-coupling reactions2
• Recyclable magnetic-nanoparticle-supported palladium catalyst for the Suzuki coupling reactions3
• Oxidative hydroxylation using a copper (Cu) catalyst4
• Ligand-free palladium-catalyzed Suzuki-Miyaura cross-coupling5
• Homocoupling using gold salts as a catalyst6
• Ruthenium (Ru)-catalyzed cross-coupling7
• CuI-catalyzed Suzuki coupling reactions8
• Palladium-catalyzed domino Heck-Mizoroki/Suzuki-Miyaura reactions9
• Manganese triacetate-mediated radical additions of arylboronic acids to alkenes10 Reagent used in Preparation of
• Pleuromutilin derivatives for ribosomal binding and antibacterial activity via "Click Chemistry"11
• Liquid crystalline polyacetylene derivatives12