Iodine monochloride
| |||
Names | |||
---|---|---|---|
Preferred IUPAC name
Iodine monochloride Iodine(I) chloride | |||
Systematic IUPAC name
Chloroiodane | |||
Other names
Iodine chloride | |||
Identifiers | |||
7790-99-0 | |||
ChemSpider | 23042 | ||
EC number | 232-236-7 | ||
| |||
Jmol-3D images | Image | ||
MeSH | Iodine-monochloride | ||
PubChem | 24640 | ||
| |||
UN number | 1792 | ||
Properties | |||
ICl | |||
Molar mass | 162.35 g/mol | ||
Appearance | red to brown liquid black crystals | ||
Density | 3.10 g/cm3 | ||
Melting point | 27.2 °C (81.0 °F; 300.3 K) (α-form) 13.9 °C (β-form) | ||
Boiling point | 97.4 °C (207.3 °F; 370.5 K) | ||
hydrolysis | |||
Solubility | soluble in CS2 acetic acid pyridine alcohol, ether, HCl | ||
Hazards | |||
MSDS | External MSDS | ||
Main hazards | corrosive | ||
Related compounds | |||
Related interhalogen compounds |
Chlorine monofluoride Bromine monochloride Iodine monobromide | ||
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | |||
verify (what is: / ?) | |||
Infobox references | |||
Iodine monochloride is an interhalogen compound with the formula ICl. It is a red-brown compound that melts 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+.
Iodine monochloride is produced simply by combining the halogens in a 1:1 molar ratio, according to the 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
ICl has two polymorphs; α-ICl which exists as black needles (red by transmitted light) with a melting point of 27.2 °C, and β-ICl which exists as black platelets (red-brown by transmitted light) with a melting point 13.9 °C.[1]
In the crystal structures of both polymorphs the molecules are arraigned in zig-zag chains. β-ICl is monoclinic with the space group P21/c.[2]
Uses
ICl is a useful reagent in organic synthesis.[1] It is used as a source of electrophilic iodine in the synthesis of certain aromatic iodides.[3] 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, the iodo-azide RCH(I)-CH(N3)R’ is obtained.[4]
Wijs solution, which is iodine monochloride dissolved in acetic acid, is used to determine the iodine value of a substance.
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
- ↑ Carpenter, G. B.; Richards, S. M. (1 April 1962). "The crystal structure of β-iodine monochloride". Acta Crystallographica 15 (4): 360–364. doi:10.1107/S0365110X62000882.
- ↑ Wallingford, V. H.; Krüger, P. A. (1943). "5-Iodo-anthranilic Acid". Org. Synth.; Coll. Vol. 2, p. 349
- ↑ Padwa, A.; Blacklock, T.; Tremper, A. "3-Phenyl-2H-Azirine-2-carboxaldehyde". Org. Synth.; Coll. Vol. 6, p. 893
|