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CAS RN: 2902-68-3 | Product Number: I0865

Iodosodilactone


Purity: >98.0%(GC)
Synonyms:
  • 2H,6H-[1,2]Iodoxolo[4,5,1-hi]benziodoxole-2,6-dione
Documents:
1G
$156.00
1   1   8  

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Product Number I0865
Purity / Analysis Method >98.0%(GC)
Molecular Formula / Molecular Weight C__8H__3IO__4 = 290.01 
Physical State (20 deg.C) Solid
Storage Temperature Room Temperature (Recommended in a cool and dark place, <15°C)
Condition to Avoid Light Sensitive
CAS RN 2902-68-3
Reaxys Registry Number 981127
PubChem Substance ID 253660633
Specifications
Appearance White to Almost white powder to crystal
Purity(Iodometric Titration) min. 98.0 %
Properties (reference)
Melting Point 263 °C
GHS
Pictogram Pictogram
Signal Word Warning
Hazard Statements H315 : Causes skin irritation.
H319 : Causes serious eye irritation.
Precautionary Statements P264 : Wash skin thoroughly after handling.
P280 : Wear protective gloves/ eye protection/ face protection.
P337 + P313 : If eye irritation persists: Get medical advice/ attention.
P305 + P351 + P338 : IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P302 + P352 : IF ON SKIN: Wash with plenty of soap and water.
P332 + P313 : If skin irritation occurs: Get medical advice/ attention.
P362 : Take off contaminated clothing and wash before reuse.
Related Laws:
Transport Information:
HS Number 2934.99.4400
Application
Recyclable Hypervalent Iodine(III) Reagent for Various Condensation Reactions

I0865

Typical procedure for preparation of esters and regeneration of iodosodilactone : A mixture of iodosodilactone (1.74 g, 6 mmol) and DMAP (733 mg, 6 mmol) in CHCl3 (50 mL) is stirred under refluxing in air for 1 h. Then, carboxylic acid (7 mmol), alcohol (611 mg, 5 mmol) and PPh3 (1.3 g, 5 mmol) are added in sequence. The mixture is refluxed for 4 h. The reaction is quenched with saturated sodium bicarbonate solution (30 mL). The aqueous layer is extracted with CH2Cl2 (50 mL×3). The combined organic layer is dried with Na2SO4, and concentrated to afford the crude product, which is purified by silica gel flash chromatography to give the corresponding ester.
The aqueous layer is acidified with 5 N HCl (pH < 7), and most of water is removed in vacuo to give the crude material. Conc. HCl (15 mL) is poured into the residue, and aq. 5.8% NaOCl soln. (35 mL) is added dropwise to the vigorously stirred mixture at room temperature. After the addition of NaOCl is complete, stirring is continued for a further 4 h. The precipitated white solid is collected by filtration, washed with H2O, diethyl ether, and acetone, and dried at room temperature to give 1.63 g of iodosodilactone in 94% recovery yield.

References


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