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208221

Sigma-Aldrich

Iodine monochloride

reagent grade, ≥95%

Synonym(s):

Chloroiodide

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About This Item

Linear Formula:
ICl
CAS Number:
7790-99-0
Molecular Weight:
162.36
EC Number:
232-236-7
MDL number:
MFCD00011354
UNSPSC Code:
12352300
PubChem Substance ID:
329752040
NACRES:
NA.21

grade

reagent grade

Quality Level

200

Assay

≥95%

form

solid or liquid

bp

97.4 °C (lit.)

density

3.24 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

ClI

InChI

1S/ClI/c1-2

InChI key

QZRGKCOWNLSUDK-UHFFFAOYSA-N

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General description

Iodine monochloride is an interhalogen compound. It forms various complexes with ethyl, isopropyl and t-butylbenzenes. Electrically conducting solution of ICl is obtained on dissolution of ICl in polar solvents. ICl is a green oxidizing agent and participates in the following transformations:
  • aldose hemiacetals to the corresponding aldose lactones
  • diarylmethanols to the corresponding diarylmethanones
  • arylalkylmethanols to the corresponding arylalkylmethanones
  • dialkylmethanols to the corresponding dialkylmethanones

Application

Iodine monochloride (ICl) may be employed as a reagent in the following processes:
  • Halogenation of methoxy and dimethoxybenzenes
  • Synthesis of flavones.
  • Preparation of 1-naphthaldehydes.
It may be used as an iodinating agent in the conversion of alkylboranes to alkyl iodides.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H314,H335

Hazard Classifications

Eye Dam. 1 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

8B - Non-combustible corrosive hazardous materials

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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Synthesis of 1-naphthaldehydes via the cascade reactions of 1-phenylpent-4-yn-2-ols promoted by iodine monochloride
Li B, et al.
Tetrahedron Letters, 57.17, 1843-1846 (2016)
A mild and convenient procedure for conversion of alkenes into alkyl iodides via reaction of iodine monochloride with organoboranes.
Kabalka GW and Gooch III EE.
The Journal of Organic Chemistry, 45(18), 3578-3580 (1980)
Iodine Monochloride (ICl) as a Highly Efficient, Green Oxidant for the Oxidation of Alcohols to Corresponding Carbonyl Compounds
Wei, Peng, et al.
Synthetic Communications, 45.12, 1457-1470 (2015)
Cation radicals as intermediates in aromatic halogenation with iodine monochloride: solvent and salt effects on the competition between chlorination and iodination.
Hubig SM, et al.
The Journal of Organic Chemistry, 59(21), 6233-6244 (1994)
Polymethylbenzene complexes of iodine and iodine monochloride.
Andrews LJ and Keefer RM.
Journal of the American Chemical Society, 74(18), 4500-4503 (1952)
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