Iodoform (also known as tri-iodomethane, carbon triiodide, and methyl triiodide) is the organoiodine compound with the formula CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.
|Preferred IUPAC name
3D model (JSmol)
|Molar mass||393.73 g·mol−1|
|Appearance||Pale, light yellow, opaque crystals|
|Density||4.008 g cm−3|
|Melting point||119 °C (246 °F; 392 K) |
|Boiling point||218 °C (424 °F; 491 K) |
|100 mg L−1|
|Solubility in diethyl ether||136 g L−1|
|Solubility in acetone||120 g L−1|
|Solubility in ethanol||78 g L−1|
|3.4 μmol Pa−1 kg−1|
Heat capacity (C)
|157.5 J K−1 mol−1|
Std enthalpy of
|180.1–182.1 kJ mol−1|
Std enthalpy of
|−716.9 – −718.1 kJ mol−1|
|GHS signal word||WARNING|
|H315, H319, H335|
|P261, P280, P305+351+338|
|Flash point||204 °C (399 °F; 477 K)|
|Lethal dose or concentration (LD, LC):|
LD50 (median dose)
|US health exposure limits (NIOSH):|
|0.6 ppm (10 mg/m3)|
IDLH (Immediate danger)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Synthesis and reactionsEdit
The synthesis of iodoform was first described by Georges-Simon Serullas in 1822, by reactions of iodine vapour with steam over red-hot coals, and also by reaction of potassium with ethanolic iodine in the presence of water; and at much the same time independently by John Thomas Cooper. It is synthesized in the haloform reaction by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds: a methyl ketone (CH3COR), acetaldehyde (CH3CHO), ethanol (CH3CH2OH), and certain secondary alcohols (CH3CHROH, where R is an alkyl or aryl group).
The reaction of iodine and base with methyl ketones is so reliable that the "iodoform test" (the appearance of a yellow precipitate) is used to probe the presence of a methyl ketone. This is also the case when testing for specific secondary alcohols containing at least one methyl group in alpha-position.
Some reagents (e.g. hydrogen iodide) convert iodoform to diiodomethane. Also conversion to carbon dioxide is possible: Iodoform reacts with aqueous silver nitrate to produce carbon monoxide. When treated with powdered elemental silver the iodoform is reduced, producing acetylene. Upon heating iodoform decomposes to produce diatomic iodine, hydrogen iodide gas, and carbon.
The angel's bonnet mushroom contains iodoform, and shows its characteristic odor.
The compound finds small-scale use as a disinfectant. Around the beginning of the 20th century, it was used in medicine as a healing and antiseptic dressing for wounds and sores, although this use is now superseded by superior antiseptics. Adolf Hitler's mother, Klara Hitler, was treated with iodoform. Some have suggested that she died of iodoform poisoning, but metastasizing breast cancer was likely the primary cause of death. It is the active ingredient in many ear powders for dogs and cats, along with zinc oxide and propanoic acid, which are used to prevent infection and facilitate removal of ear hair.
- "Front Matter". Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 661. doi:10.1039/9781849733069-FP001. ISBN 978-0-85404-182-4.
The retained names ‘bromoform’ for HCBr3, ‘chloroform’ for HCCl3, and ‘iodoform’ for HCI3 are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.
- Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- "NIOSH Pocket Guide to Chemical Hazards #0343". National Institute for Occupational Safety and Health (NIOSH).
- Merck Index, 12 Edition, 5054
- Surellas, Georges-Simon (1822), Notes sur l'Hydriodate de potasse et l'Acide hydriodique. -- Hydriodure de carbone; moyen d'obtenir, à l'instant, ce composé triple [Notes on the hydroiodide of potassium and on hydroiodic acid -- hydroiodide of carbon; means of obtaining instantly this compound of three elements] (in French), Metz, France: Antoine, pp. 17–20, 28–29
- James, Frank A. J. L. "Cooper, John Thomas (1790–1854), chemist". Oxford Dictionary of National Biography. Oxford University Press. Retrieved 26 January 2012.
- Lyday, Phyllis A. (2005), "Iodine and Iodine Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, pp. 1–13, doi:10.1002/14356007.a14_381.pub2, ISBN 9783527306732