Iodoform
- for use of the term "iodoform" in cryptography, see Group key
| Stereo, skeletal formula of iodoform with the explicit hydrogen added | |||
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| Sample of crystalline iodoform in a watchglass | |||
| Names | |||
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| Other names
Triiodomethane
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| Identifiers | |||
75-47-8  |
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| 1697010 | |||
| ChEBI | CHEBI:37758 |
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| ChEMBL | ChEMBL1451116  |
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| ChemSpider | 6134 |
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| EC Number | 200-874-5 | ||
| Jmol 3D model | Interactive image | ||
| KEGG | D01910 |
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| MeSH | iodoform | ||
| PubChem | 6374 | ||
| RTECS number | PB7000000 | ||
| UNII | KXI2J76489 |
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| Properties | |||
| CHI3 | |||
| Molar mass | 393.73 g·mol−1 | ||
| Appearance | Pale, light yellow, opaque crystals | ||
| Odor | Saffron-like[1] | ||
| Density | 4.008 g mL−1[1] | ||
| Melting point | 119 °C (246 °F; 392 K) [1] | ||
| Boiling point | 218 °C (424 °F; 491 K) [1] | ||
| 100 mg L−1[1] | |||
| Solubility in diethyl ether | 136 g L−1 | ||
| Solubility in acetone | 120 g L−1 | ||
| Solubility in ethanol | 78 g L−1 | ||
| log P | 3.118 | ||
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Henry's law
constant (kH) |
3.4 μmol Pa−1 kg−1 | ||
| Structure | |||
| Hexagonal | |||
| Tetragonal | |||
| Tetrahedron | |||
| Thermochemistry | |||
| 157.5 J K−1 mol−1 | |||
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Std enthalpy of
formation (ΔfH |
180.1–182.1 kJ mol−1 | ||
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Std enthalpy of
combustion (ΔcH |
−716.9–−718.1 kJ mol−1 | ||
| Pharmacology | |||
| ATC code | D09 | ||
| Vapor pressure | {{{value}}} | ||
| Related compounds | |||
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Related haloalkanes
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Related compounds
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Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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 verify (what is ?) |
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| Infobox references | |||
Iodoform 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. It is also known as tri-iodomethane, carbon triiodide, and methyl triiodide.
Contents
Synthesis and reactions
The synthesis of Iodoform was first described by Georges Serrulas 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;[2] and at much the same time independently by John Thomas Cooper.[3] 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: (i) 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 secondary alcohols (methyl alcohols).
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.
Natural occurrence
Angel's bonnets contain iodoform and show its characteristic odor.
Applications
The compound finds small scale use as a disinfectant.[4][5] 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, died of iodoform poisoning brought on by her treatment for breast cancer. 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.[citation needed]
See also
References
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- MSDS at JT Baker
- A Method for the Specific Conversion of Iodoform to Carbon Dioxide
- Article at 1911 Encyclopaedia Britannica
- Preparation
- ↑ 1.0 1.1 1.2 1.3 1.4 Record in the GESTIS Substance Database of the IFA
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