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Merck
CN

743739

Sigma-Aldrich

2H,6H-[1,2]Iodoxolo[4,5,1-hi][1,2]benziodoxole-2,6-dione

96.0-104.0 wt. % (T)

Synonym(s):

2aλ3-Ioda-2,3-dioxa-cyclopenta[cd]indene-1,4-dione, Iodosodilactone

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About This Item

Empirical Formula (Hill Notation):
C8H3IO4
CAS Number:
2902-68-3
Molecular Weight:
290.01
MDL number:
MFCD24386358
UNSPSC Code:
12352005
PubChem Substance ID:
329765653
NACRES:
NA.22

Key Documents

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Assay

96.0-104.0% (wt., T)

form

solid

functional group

iodo

SMILES string

O=C1O[I]2OC(=O)c3cccc1c23

InChI

1S/C8H3IO4/c10-7-4-2-1-3-5-6(4)9(12-7)13-8(5)11/h1-3H

InChI key

DHIWEENQJCGNME-UHFFFAOYSA-N

Application

2H,6H-[1,2]Iodoxolo[4,5,1-hi][1,2]benziodoxole-2,6-dione is an iodine(III) reagent that can be used:
  • As a coupling reagent in many organic reactions like amidation, peptide coupling, and esterification to yield amides, esters, peptides, and macrocyclic lactones without racemization.
  • As an oxidant in the arylation reactions of fluorophenols.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBK6212V
BCBK6212

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Synthesis and properties of two iodosolactones.
Agosta, W. C.
Tetrahedron Letters, 6, 2681-2685 (1965)
Regioselective oxidative arylation of fluorophenols
Yu C and Patureau FW
Angewandte Chemie (International Edition in English), 58(51), 18530-18534 (2019)
Jun Tian et al.
Organic letters, 14(12), 3020-3023 (2012-06-08)
A hypervalent iodine(III) reagent plays a novel role as an efficient coupling reagent to promote the direct condensation between carboxylic acids and alcohols or amines to provide esters, macrocyclic lactones, amides, as well as peptides without racemization. The regeneration of
Recyclable hypervalent iodine (III) reagent iodosodilactone as an efficient coupling reagent for direct esterification, amidation, and peptide coupling
Tian J, et al.
Organic Letters, 14(12), 3020-3023 (2012)

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