Iodine monochloride
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| Iodine monochloride | |
|---|---|
| Image:Iodine-monochloride-2D.png Image:Iodine-monochloride-3D-vdW.png | |
| General | |
| Systematic name | iodine(I) chloride |
| Other names | iodine chloride |
| Molecular formula | ICl |
| SMILES | ICl |
| Molar mass | 162.35 g/mol |
| Appearance | red to brown liquid |
| CAS number | [7790-99-0] |
| Properties | |
| Density and phase | 3.10 g/cm3 |
| Solubility in water | hydrolysis |
| Other solvents | carbon disulfide acetic acid pyridine |
| Melting point | 27°C (α-form) |
| Boiling point | 97.4°C (370.6 K) |
| Structure | |
| Crystal structure | ? |
| Dipole moment | ? D |
| Hazards | |
| MSDS | External MSDS |
| Main hazards | corrosive |
| NFPA 704 | |
| R/S statement | R: ? S: ? |
| RTECS number | ? |
| Supplementary data page | |
| Structure and properties | n, É√r, etc. |
| Thermodynamic data | Phase behaviour Solid, liquid, gas |
| Spectral data | UV, IR, NMR, MS |
| Related compounds | |
| Related interhalogen compounds | Chlorine monofluoride, bromine monochloride, iodine monobromide |
| Except where noted otherwise, data are given for materials in their standard state (at 25°C, 100 kPa) Infobox disclaimer and references | |
Iodine monochloride is the compound with the formula ICl. This red brown compound melts just near room temperature. Because of the difference in the electronegativity of iodine and chlorine, ICl is highly polar and behaves as a source of “I+.”
Preparation of iodine monochloride entails simply combining the halogens in a 1:1 molar ratio, according to this equation:
- I2 + Cl2 → 2 ICl
When chlorine gas is passed through iodine crystals, one observes the brown vapor of iodine monochloride. Dark brown iodine monochloride liquid is collected. Excess chlorine converts iodine monochloride into iodine trichloride in a reversible reaction:
- ICl + Cl2 → ICl3
Polymorphs
Polymorphy is the phenomenon where a solid exists in two or more different crystalline forms. ICl has two polymorphs, α-ICl which are black needles (red by transmitted light) with a melting point of 27.2 °C and β-ICl which are black platelets (red-brown by transmitted light) with a melting point 13.9 °C.[1]
Uses
ICl is a useful reagent in organic synthesis.[1] It is used as a source of electrophilic iodine to synthesise certain aromatic iodides.[2] It also cleaves C-Si bonds.
ICl, will also add to the double bond in alkenes to give chloro-iodo alkanes.
- RCH=CHR’ + ICl → RCH(I)-CH(Cl)R’
When such reactions are conducted in the presence of sodium azide, one obtains the iodo-azide, RCH(I)-CH(N3)R’.[3]
References
- ↑ 1.0 1.1 Brisbois, R. G.; Wanke, R. A.; Stubbs, K. A.; Stick, R. V. “Iodine Monochloride” Encyclopedia of Reagents for Organic Synthesis, 2004 John Wiley & Sons. DOI: 10.1002/047084289X.ri014
- ↑ Wallingford, V. H.; Krüger, P. A. "5-Iodo-anthranilic Acid" Organic Syntheses, Collected Volume 2, p.349 (1943). http://www.orgsyn.org/orgsyn/pdfs/CV2P0349.pdf
- ↑ Padwa, A.; Blacklock, T.; Tremper, A. "3-Phenyl-2H-Azirine-2-carboxaldehyde" Organic Syntheses, Collected Volume 6, p.893 (1988). http://www.orgsyn.org/orgsyn/pdfs/CV6P0893.pdf
External links
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
