Iodoform
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| Names | |||
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| Preferred IUPAC name
Triiodomethane | |||
| Other names
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| Identifiers | |||
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3D model (JSmol)
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| 1697010 | |||
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| MeSH | iodoform | ||
PubChem CID
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| Properties | |||
| CHI3 | |||
| Molar mass | 393.732 g·mol−1 | ||
| Appearance | Pale, light yellow, opaque crystals | ||
| Odor | Saffron-like, sweetish[2] | ||
| Density | 4.008 g/cm3[2] | ||
| Melting point | 119 °C (246 °F; 392 K)[2] | ||
| Boiling point | 218 °C (424 °F; 491 K)[2] | ||
| 100 mg/L[2] | |||
| Solubility in diethyl ether | 136 g/L | ||
| Solubility in acetone | 120 g/L | ||
| Solubility in ethanol | 78 g/L | ||
| log P | 3.118 | ||
Henry's law
constant (kH) |
3.4 μmol·Pa−1·kg−1 | ||
| −117.1·10−6 cm3/mol | |||
| Structure | |||
| Hexagonal | |||
| Tetrahedral at C | |||
| Thermochemistry | |||
Heat capacity (C)
|
157.5 J/(K·mol) | ||
Std enthalpy of
formation (ΔfH⦵298) |
180.1 – 182.1 kJ/mol | ||
Std enthalpy of
combustion (ΔcH⦵298) |
−716.9 – −718.1 kJ/mol | ||
| Pharmacology | |||
| D09AA13 (WHO) | |||
| Hazards | |||
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| Flash point | 204 °C (399 °F; 477 K) | ||
| Lethal dose or concentration (LD, LC): | |||
LD50 (median dose)
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| NIOSH (US health exposure limits): | |||
PEL (Permissible)
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none[3] | ||
REL (Recommended)
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0.6 ppm (10 mg/m3)[3] | ||
IDLH (Immediate danger)
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N.D.[3] | ||
| Related compounds | |||
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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Template:Chembox Footer/trackingTemplate:Short description
Iodoform (also known as triiodomethane) is the organoiodine compound with the chemical formula Page Module:Chem2/styles.css has no content.CHI3. It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive sweetish and chloroform-like odor (in older chemistry texts, the smell is sometimes referred to as that of hospitals, where the compound is still commonly used) and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.
Naming
The name iodoform originates with the "formyle radical," an archaic term for the HC moiety,[5][6] and is retained for historical consistency. A full, modern name is triiodomethane.
Structure
The molecule adopts a tetrahedral geometry with C3v symmetry.
Synthesis and reactions
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;[7] and at much the same time independently by John Thomas Cooper.[8] 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 (Page Module:Chem2/styles.css has no content.CH3COR), acetaldehyde (Page Module:Chem2/styles.css has no content.CH3CHO), ethanol (Page Module:Chem2/styles.css has no content.CH3CH2OH), and certain secondary alcohols (Page Module:Chem2/styles.css has no content.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. Conversion to carbon dioxide is also possible.[9] 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
The angel's bonnet mushroom contains iodoform, and shows its characteristic odor.
Applications
The compound finds small-scale use as a disinfectant.[4][10] Around the beginning of the 20th century, it was used in medicine as a healing and antiseptic dressing for wounds and sores and, although this use is now largely superseded by safer antiseptics,[11] it is still used in otolaryngology in the form of bismuth subnitrate iodoform paraffin paste (BIPP) as an antiseptic packing for cavities.[12] It is the active ingredient in many ear powders for dogs and cats, along with zinc oxide and boric acid, which are used to prevent infection and facilitate removal of ear hair.[citation needed]
See also
References
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- ^ Page Module:Citation/CS1/styles.css has no content."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.
- ^ a b c d e f g Record in the GESTIS Substance Database of the Institute for Occupational Safety and Health
- ^ a b c Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0343". National Institute for Occupational Safety and Health (NIOSH).
- ^ a b Merck Index, 12 Edition, 5054
- ^ Page Module:Citation/CS1/styles.css has no content.Raige-Delorme, Jacques; Bouley, H.; Daremberg, C.; Mignon, J.; Lamy, Charles (1863). Nouveau Dictionnaire lexicographique et descriptif des Sciences médicales et vétérinaires ... avec planches intercalées dans le texte, suivi d'un vocabulaire biographique. Par Messieurs Raige-Delorme, H. Bouley, C. Daremberg, J. Mignon, avec la collaboration de M. Ch. Lamy, pour la Chimie (in français). p. 520.
Formyle, s. m. Nom donné par Liebig au radical hypothétique (C2H) de l'ac. formique, du chloroforme, du bromoforme, de l'iodoforme, etc.
[Formyle, masculine noun. Name given by Liebig to the hypothetical radical (C2H) of formic acid, chloroform, bromoform, iodoform, etc.] - ^ At the time, the atomic weight of carbon was thought to be half of its true value: Page Module:Citation/CS1/styles.css has no content.Rocke, Alan J. [in Deutsch] (1993). The quiet revolution: Hermann Kolbe and the science of organic chemistry. Berkeley: University of California Press. p. 158. ISBN 9780520081109.
- ^ Page Module:Citation/CS1/styles.css has no content.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
{{citation}}: CS1 maint: unrecognized language (link) - ^ Script error: No such module "template wrapper". (Subscription, Wikipedia Library access or UK public library membership required.)
- ^ Page Module:Citation/CS1/styles.css has no content.Shreeve, W. W.; Leaver, F.; Siegel, I. (1952). "A Method for the Specific Conversion of Iodoform to Carbon Dioxide". J. Am. Chem. Soc. 74 (9): 2404. Bibcode:1952JAChS..74.2404S. doi:10.1021/ja01129a067.
- ^ Page Module:Citation/CS1/styles.css has no content.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
- ^ Page Module:Citation/CS1/styles.css has no content.Gottardi, Waldemar (1 January 2001). "Iodine and Iodine Compounds". In Block, Seymour Stanton (ed.). Disinfection, Sterilization, and Preservation (5th ed.). Lippincott Williams & Wilkins. p. 176. ISBN 978-0-683-30740-5.
- ^ Page Module:Citation/CS1/styles.css has no content.Randhawa, G. K.; Graham, R.; Matharu, K. S. (2019). "Bismuth Iodoform Paraffin Paste: History and uses". British Journal of Oral and Maxillofacial Surgery. 57 (10): E53–E54. doi:10.1016/j.bjoms.2019.10.153.
External links
- Page Module:Citation/CS1/styles.css has no content.NIOSH Pocket Guide to Chemical Hazards. "#0343". National Institute for Occupational Safety and Health (NIOSH).
- Preparation
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