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402990

Sigma-Aldrich

Iodine monochloride

ACS reagent, 1.10±0.1 I/Cl ratio basis

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:
329755974
NACRES:
NB.24

grade

ACS reagent

form

solid or liquid

impurities

≤0.005% insolubles

bp

97.4 °C (lit.)

solubility

acetic acid: soluble(lit.)
acetone: soluble(lit.)
alcohol: soluble(lit.)
carbon disulfide: soluble(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. Equilibrium constants for the formation of these complexes have been evaluated. It affords electrically conducting solution on dissolution in polar solvents. Its reaction with thymidine, 3-mono- and 3,3′,5′-trialkylsubstitued thymidine showed that it helps in deglycosylation, anomerization and isomerization of thymidine.

Application

Iodine monochloride (ICl) may be employed for the halogenation of methoxy and dimethoxybenzenes. It may be used for the synthesis of flavones.
Iodine monochloride may be used in the synthesis of the following:
  • 2-(4-haloisoquinolin-1-yl)ethanol derivatives
  • 5-iodosalicylaldehydes
  • 5-aryl-6-iodo-8-phenylpyrazolo[1,5-c]-1,2,4-triazolo[4,3-a]pyrimidines
  • (±)-1-cyclohexyl-4-iodo-3-methoxybutan-1-ol
  • (±)-4-Iodo-3-methoxy-1-phenylbutan-1-ol

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)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Synthesis of Luminescent Ethynyl-Extended Regioisomers of Borate Complexes Based on 2-(2'-Hydroxyphenyl) benzoxazole.
23 Massue J, et al.
Chemistry (Weinheim An Der Bergstrasse, Germany), 19(17), 5375-5386 (2013)
Three-Component Reactions of 2-Alkynylbenzaldoximes and α, β-Unsaturated Carbonyl Compounds with Bromine or Iodine Monochloride.
Ye S, et al.
Advanced Synthesis & Catalysis, 352(10), 1746-1751 (2010)
Eagleson M.
Concise Encyclopedia Chemistry, 477-477 (1994)
Brisbois RG, et al.
e-EROS Encyclopedia of Reagents for Organic Synthesis. (2013)
Eric Stefan et al.
Tetrahedron, 69(36), 7706-7712 (2013-09-24)
Ether transfer methodology is capable of stereoselectively generating 1,3-diol mono- and diethers in good yield. Surprisingly, allylic and benzylic substrates provide none of the desired products when exposed to previously optimized conditions of iodine monochloride. Herein, second-generation activation conditions for
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