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743739

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

Name: 2H,6H-[1,2]Iodoxolo[4,5,1-hi][1,2]benziodoxole-2,6-dione
Brand: ALDRICH

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

This product is discontinued. Contact Technical Servicefor assistance.

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.[1]
As an oxidant in the arylation reactions of fluorophenols.[2]

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P305 + P351 + P338

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

BCBK6212V

BCBK6212

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Sigma-Aldrich

696641

3,3-Dimethyl-1-(trifluoromethyl)-1,2-benziodoxole

Sigma-Aldrich

771147

1-Trifluoromethyl-1,2-benziodoxol-3-(1H)-one

Recyclable hypervalent iodine(III) reagent iodosodilactone as an efficient coupling reagent for direct esterification, amidation, and peptide coupling.

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)

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)

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