Carbon tetraiodide is CI₄. Being bright red, it is a relatively rare example of a highly colored methane derivative. It is only 2% by weight carbon, although other methane derivatives are known with still less carbon. The tetrahedral molecule features C-I distances of 2.12 ± 0.02 Å. The molecule is slightly crowded with short I---I contacts of 3.459 ± 0.03 Å, and possibly for this reason, it is thermally and photochemically unstable. Hexaiodoethane is unknown, probably for the same reason. IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... Molar mass is the mass of one mole of a chemical element or chemical compound. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... Density (symbol: ρ - Greek: rho) is a measure of mass per unit of volume. ... In the physical sciences, a phase is a set of states of a macroscopic physical system that have relatively uniform chemical composition and physical properties (i. ... A substance is soluble in a fluid if it dissolves in that fluid. ... Water has the chemical formula H2O, meaning that one molecule of water is composed of two hydrogen atoms and one oxygen atom. ... The melting point of a solid is the temperature at which it changes state from solid to liquid. ... four sp³ orbitals three sp² orbitals In chemistry, hybridisation is the mixing of atomic orbitals belonging to a same electron shell to form new orbitals suitable for the qualitative description of atomic bonding properties. ... Rose des Sables (Sand Rose), formed of gypsum crystals In mineralogy and crystallography, a crystal structure is a unique arrangement of atoms in a crystal. ... In crystallography, the monoclinic crystal system is one of the 7 lattice point groups. ... The Earths magnetic field, which is approximately a dipole. ... The debye (symbol: D) is a non-SI and non-CGS unit of electrical dipole moment. ... A material safety data sheet or MSDS is a form containing data regarding the properties of a particular substance. ... Worker safety and health is the prevention and reduction of the number of occupational safety and health hazards at the places of employment, providing safe and healthful working conditions. ... NFPA 704 is a standard maintained by the U.S. National Fire Protection Association. ... Risk and Safety Statements, also known as R/S statements, R/S numbers, R/S phrases, and R/S sentences, is a system of hazard codes and phrases for labeling dangerous chemicals and compounds. ... R-phrases are defined in Annex III of European Union Directive 67/548/EEC: Nature of special risks attributed to dangerous substances and preparations. ... S-phrases are defined in Annex IV of European Union Directive 67/548/EEC: Safety advice concerning dangerous substances and preparations. ... RTECS, also known as Registry of Toxic Effects of Chemical Substances, is a database of toxicity information compiled from the open scientific literature that is available for charge. ... The refractive index of a material is the factor by which the phase velocity of electromagnetic radiation is slowed relative to vacuum. ... The dielectric constant εr (represented as or K in some cases) is defined as the ratio: where εs is the static permittivity of the material in question, and ε0 is the vacuum permittivity. ... Ultraviolet-Visible Spectroscopy or Ultraviolet-Visible Spectrophotometry (UV/ VIS) involves the spectroscopy of photons (spectrophotometry). ... IR spectrum of a thin film of liquid ethanol. ... Nuclear Magnetic Resonance Spectroscopy most commonly known as NMR Spectroscopy is the name given to the technique which exploits the magnetic properties of nuclei. ... It has been suggested that Mass spectrum be merged into this article or section. ... R-phrases , , , , S-phrases , , , , , Flash point non flammable RTECS number FG4900000 Supplementary data page Structure and properties n, εr, etc. ... The compound iodoform is a yellow, crystalline, volatile substance, I3CH, having a penetrating odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals) and sweetish taste, and analogous to chloroform. ... In chemistry, the standard state of a material is its state at 1 bar (100 kilopascals) and 25 degrees Celsius (298. ...

Properties, synthesis, uses

CI₄ is slightly reactive water giving iodoform and I₂. Otherwise it is soluble in nonpolar organic solvents. It decomposes thermally and photochemically to tetraiodoethylene, I₂C=CI₂. Its synthesis entails AlCl₃-catalyzed halide exchange, which is conducted at room temperature: Aluminium chloride (AlCl3) is a compound of aluminium and chlorine. ...

CCl₄ + 4 EtI → CI₄ + 4 EtCl

The product crystallizes from the reaction solution.

CI₄ is used as an iodination reagent, often upon reaction with base. Ketones are converted to 1,1-diiodoethenes upon treatment with PPh₃ and CI₄. Alcohols are converted in and to iodid, by an mechanism similar to the Appel reaction. In an Appel reaction carbon tetrachloride is used to generate the chloride from alcohls. Flash point 180 °C RTECS number SZ3500000 Supplementary data page Structure and properties n, εr, etc. ... The Appel reaction is a chemical reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride. ... R-phrases , , , , S-phrases , , , , , Flash point non flammable RTECS number FG4900000 Supplementary data page Structure and properties n, εr, etc. ...

Safety considerations

Manufacturers recommend that CI₄ be stored near 0 °C. As a ready source of iodine, it is an irritant. LD50: 178 mg kg–1. In general perhalogenated organic compounds should be considered toxic.

Suppliers

Aldrich

References

• McArthur, R. E.; Simons, J. H., “Carbon Tetraiodide” Inorganic Syntheses 1950, volume III, 37–39.
• P. R. Schreiner, A. A. Fokin, “Carbon Tetraiodide” in Encyclopedia of Reagents for Organic Synthesis (Ed: L. Paquette) 2005; John Wiley & Sons, Ltd.
• Sorros, H., Hinkam J. B. , “The Redistribution Reaction. XI. Application to the Preparation of Carbon Tetraiodide and Related Halides” Journal of the American Chemical Society 1945, 67, 1643. DOI
• Finbak, Chr.; Hassel, O. Kristallstruktur und Molekülbau von CI₄ und CBr₄" Zeitschrifte für Physikalische Chemie (1937), volume B36, page 301-8.