743739
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:
Molecular Weight:
290.01
NACRES:
NA.22
PubChem Substance ID:
UNSPSC Code:
12352005
MDL number:
Assay:
96.0-104.0% (wt., T)
Form:
solid
InChI
1S/C8H3IO4/c10-7-4-2-1-3-5-6(4)9(12-7)13-8(5)11/h1-3H
SMILES string
O=C1O[I]2OC(=O)c3cccc1c23
InChI key
DHIWEENQJCGNME-UHFFFAOYSA-N
assay
96.0-104.0% (wt., T)
form
solid
functional group
iodo
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.
signalword
Warning
hcodes
Hazard Classifications
Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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Regioselective oxidative arylation of fluorophenols
Yu C and Patureau FW
Angewandte Chemie (International Edition in English), 58(51), 18530-18534 (2019)
Synthesis and properties of two iodosolactones.
Agosta, W. C.
Tetrahedron Letters, 6, 2681-2685 (1965)
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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