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232130 Sigma-Aldrich

[Bis(trifluoroacetoxy)iodo]benzene

97%

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 24853882

  •  NACRES NA.22

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Properties

Related Categories Chemical Synthesis, Hypervalent Iodine, Oxidizing Agents, Synthetic Reagents
assay   97%
mp   121-125 °C (lit.)
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

Used for the direct α-hydroxylation of ketones under acidic conditions. Also employed as a p-fluorination reagent of 4-alkylphenols in the presence of HF·pyridine (cat. no. 184225) for synthesis of 4-fluorocyclohexa-2,5-dienones.
Reagent for the oxidation of N-acylhydrazones to 1,3,4-oxadiazoles. Promotes the cyclization of styryl amines to N-alkyl or N-aryl indoles.

Packaging

10, 50 g in glass bottle

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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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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