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Sigma-Aldrich

Iodine

ACS reagent, ≥99.8%, solid

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Empirical Formula (Hill Notation):
I2
CAS Number:
7553-56-2
Molecular Weight:
253.81
Beilstein:
3587194
EC Number:
231-442-4
MDL number:
MFCD00011355
eCl@ss:
38050601
PubChem Substance ID:
329752021
NACRES:
NA.21

grade

ACS reagent

Quality Level

200

vapor density

9 (vs air)

vapor pressure

0.31 mmHg ( 25 °C)
1 mmHg ( 38.7 °C)

Assay

≥99.8%

form

solid

resistivity

1.3E15 μΩ-cm

impurities

≤0.01% nonvolatiles

bp

184 °C (lit.)

mp

113 °C (lit.)

anion traces

Cl- and Br-: ≤0.005%

storage temp.

room temp

SMILES string

II

InChI

1S/I2/c1-2

InChI key

PNDPGZBMCMUPRI-UHFFFAOYSA-N

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General description

Iodine exhibits exceptionally high dielectric polarization in various solvents (dioxane, isobutylene, p-xylene and benzene).

Application

Catalyst for synthesis of esters by condensation of carboxylic acids with alcohols or transfesterification.

A mild and efficient method for esterification and transesterification catalyzed by iodine
Iodine has been used for the easy visualization of 9-bromononanoic acid, allyl ester by thin layer chromatography (TLC). It has also been used for the preparation of oxidation solution, required for the synthesis of oligodeoxynucleotides bearing 3′-terminal phosphorothioate.
Iodine may be used to catalyze:
  • Synthesis of 5-(4-nitrophenyl)-10,15,20-triphenylporphyrin.
  • Oxidative C-H bond amination of saturated hydrocarbons.
  • Protection of amines with benzyloxycarbonyl (Cbz) group.
  • Direct oxidative coupling/annulation of β-keto esters or 2-pyridinyl-β-esters with alkenes to form dihydrofurans and indolizine, respectively.
  • Thiocyanation of aromatic systems to form aryl thiocyanates.
  • Esterification of cellulose with acetic anhydride to form cellulose triacetate.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Acute 1 - Eye Irrit. 2 - Skin Irrit. 2 - STOT RE 1 Oral - STOT SE 3

Target Organs

Respiratory system, Thyroid

Storage Class Code

6.1D - Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Iodine/MeOH: a novel and efficient reagent system for thiocyanation of aromatics and heteroaromatics.
Yadav JS, et al.
Tetrahedron Letters, 45(14), 2951-2954 (2004)
Molecular iodine-catalyzed efficient N-Cbz protection of amines.
Varala R, et al.
Journal of the Iranian Chemical Society, 4(3), 370-374 (2007)
Iodine catalyzed esterification of cellulose using reduced levels of solvent.
Biswas A, et al.
Carbohydrate Polymers, 68(3), 555-560 (2007)
Iodine-Catalyzed Radical Oxidative Annulation for the Construction of Dihydrofurans and Indolizines.
Tang S, et al.
Organic Letters, 17(10), 2404-2407 (2015)
Iodine-catalyzed one-pot synthesis of unsymmetrical meso-substituted porphyrins.
Boens B, et al.
Tetrahedron, 66(11), 1994-1996 (2010)
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