(3-iodophenyl)boronic acid

• ChemBase ID: 69652
• Molecular Formular: C6H6BIO2
• Molecular Mass: 247.82611
• Monoisotopic Mass: 247.95055783
• SMILES: c1(cc(ccc1)I)B(O)O
• Canonical SMILES: Ic1cccc(c1)B(O)O
• InChI: InChI=1S/C6H6BIO2/c8-6-3-1-2-5(4-6)7(9)10/h1-4,9-10H
• InChIKey: REEUXWXIMNEIIN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3-iodophenyl)boronic acid
• IUPAC Traditional name: 3-iodophenylboronic acid
• Synonyms: 3-Iodophenylboronic acid; 3-Iodophenylboronic acid; 3-Iodophenylboronic acid; 3-Iodobenzeneboronic acid; 3-碘苯硼酸

Database IDs

• CAS Number: 221037-98-5
• MDL Number: MFCD01319015
• PubChem SID: 162035378; 24867695
• PubChem CID: 2734362

CALCULATED PROPERTIES

• Acid pKa: 8.680331
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.630115
• LogD (pH = 7.4): 2.6083205
• Log P: 2.6304
• Molar Refractivity: 43.966 cm^3
• Polarizability: 18.743092 Å^3
• Polar Surface Area: 40.46 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 195-197 °C(lit.)

Safety Information

• Storage Warning: 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+%; 97%; 98%
• Linear Formula: IC6H4B(OH)2

DETAILS

Sigma Aldrich - 441678

Other Notes
Contains varying amounts of anhydride
Packaging
5 g in glass bottle
Application
Reactant involved in:
• Aerobic oxidative coupling with arenes1
• Coupling with acetals2
• Synthesis of inhibitors of homoserine transacetylase3
• Boron-Heck arylation with alkenes4
• N-arylation5
• Heck reactions with electrophilic alkenes6