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Merck

207772

Iodine

ACS reagent, ≥99.8%, solid

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About This Item

Empirical Formula (Hill Notation):
I2
CAS Number:
7553-56-2
Molecular Weight:
253.81
NACRES:
NA.21
PubChem Substance ID:
329752021
eCl@ss:
38050601
UNSPSC Code:
12141916
EC Number:
231-442-4
MDL number:
MFCD00011355
Beilstein/REAXYS Number:
3587194
assay:
≥99.8%
grade:
ACS reagent
form:
solid

Product Name

Iodine, ACS reagent, ≥99.8%, solid

InChI key

PNDPGZBMCMUPRI-UHFFFAOYSA-N

InChI

1S/I2/c1-2

SMILES string

II

grade

ACS reagent

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

Quality Level

200

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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.

General description

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

signalword

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

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCZ8360
MKCZ2185
MKCZ0552
MKCX8416
MKCX7018

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Iodine-catalyzed one-pot synthesis of unsymmetrical meso-substituted porphyrins.
Boens B, et al.
Tetrahedron, 66(11), 1994-1996 (2010)
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)
An Iodine-Catalyzed Hofmann-Loffler Reaction.
Martinez C and Mu?iz K.
Angewandte Chemie (International Edition in English), 54(28), 8287-8291 (2015)
Julien A Boos et al.
Nucleic acids research, 41(15), e145-e145 (2013-06-15)
Efficient tissue-specific delivery is a crucial factor in the successful development of therapeutic oligonucleotides. Screening for novel delivery methods with unique tissue-homing properties requires a rapid, sensitive, flexible and unbiased technique able to visualize the in vivo biodistribution of these
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