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15230 Sigma-Aldrich

[Bis(trifluoroacetoxy)iodo]benzene

purum, ≥95.0% (AT)

Synonym: BTI, Iodobenzene I,I-bis(trifluoroacetate), PIFA

  • CAS Number 2712-78-9

  • Linear Formula (CF3CO2)2IC6H5

  • Molecular Weight 430.04

  •  Beilstein/REAXYS Number 764767

  •  EC Number 220-308-0

  •  MDL number MFCD00009672

  •  PubChem Substance ID 329750783

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Hypervalent Iodine, Oxidizing Agents, Synthetic Reagents
Quality Level   200
grade   purum
assay   ≥95.0% (AT)
mp   121-125 °C (lit.)
  122-125 °C
SMILES string   FC(F)(F)C(=O)O[I](OC(=O)C(F)(F)F)c1ccccc1
InChI   1S/C10H5F6IO4/c11-9(12,13)7(18)20-17(6-4-2-1-3-5-6)21-8(19)10(14,15)16/h1-5H
InChI key   PEZNEXFPRSOYPL-UHFFFAOYSA-N

Description

Application

Reactant or reagent for:
• Pummerer-like reactions
• Chemoselective deprotection of dimethoxybenzyl ethers
• Mediating oxidative cycloisomerization
• Tosyloxylation of anilides

Other Notes

Reagent for dehydrogenation and oxidation reactions, review; New reagent for the direct conversions of amides to amines (Hofmann-type rearrangement) and key substance for carboxyterminal peptide sequencing; Smooth dethioacetalization to the carbonyls

Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Target organs 
Respiratory system
Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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