531634

Bis(pyridine)iodonium tetrafluoroborate

• Synonym(s): Barluenga reagent
• Empirical Formula (Hill Notation): C₁₀H₁₀BF₄IN₂
• CAS Number: 15656-28-7
• Molecular Weight: 371.91
• MDL number: MFCD03703393
• UNSPSC Code: 12352005
• PubChem Substance ID: 24877831
• NACRES: NA.22

Properties

• Quality Level: 200
• reaction suitability: reagent type: oxidant
• mp: 137-141 °C (lit.)
• storage temp.: 2-8°C
• SMILES string: [I+].F[B-](F)(F)F.c1ccncc1.c2ccncc2
• InChI: 1S/2C5H5N.BF4.I/c2*1-2-4-6-5-3-1;2-1(3,4)5;/h2*1-5H;;/q;;-1;+1
• InChI key: JBVUIHBKNVHCKK-UHFFFAOYSA-N

Description

General description

Bis(pyridine)iodonium Tetrafluoroborate (Barluenga′s reagent) is a mild iodinating and oxidizing reagent capable of selectively reacting with a wide range of unsaturated substrates and tolerates a variety of functional groups.

Application

Bis(pyridine)iodonium Tetrafluoroborate reacts with acetonides derived from simple terpenes to accomplish selective iodofunctionalization with excellent regio- and diastereofacial control. It has been used as a reactant involved in:

• Synthesis of substituted naphthalenes and oxygen containing heterocycles from 2-alkynyl-substituted benzaldehydes.
• Synthesis of tetracyclic tetrahydrofurans
  
  Applications for Bis(pyridine)iodonium Tetrafluoroborate

Safety Information

• pictograms: GHS07
• signalword: Warning
• hcodes: H315,H319,H335
• pcodes: P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338
• Hazard Classifications: 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