Iodoform

From Wikipedia, the free encyclopedia
Jump to: navigation, search
For use of the term "iodoform" in cryptography, see Group key.
Iodoform
Stereo, skeletal formula of iodoform with the explicit hydrogen added
Ball and stick model of iodoform
Spacefill model of iodoform
Sample of crystalline iodoform in a watchglass
Names
Preferred IUPAC name
Triiodomethane
Other names
Iodoform[1]
Identifiers
75-47-8 YesY
1697010
ChEBI CHEBI:37758 YesY
ChEMBL ChEMBL1451116 N
ChemSpider 6134 YesY
EC Number 200-874-5
Jmol 3D model Interactive image
KEGG D01910 YesY
MeSH iodoform
PubChem 6374
RTECS number PB7000000
UNII KXI2J76489 YesY
Properties
CHI3
Molar mass 393.73 g·mol−1
Appearance Pale, light yellow, opaque crystals
Odor Saffron-like[2]
Density 4.008 g cm−3[2]
Melting point 119 °C (246 °F; 392 K) [2]
Boiling point 218 °C (424 °F; 491 K) [2]
100 mg L−1[2]
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
3.4 μmol Pa−1 kg−1
Structure
Hexagonal
Tetragonal
Tetrahedron
Thermochemistry
157.5 J K−1 mol−1
180.1–182.1 kJ mol−1
−716.9–−718.1 kJ mol−1
Pharmacology
D09AA13 (WHO)
Hazards
GHS pictograms The exclamation-mark pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word WARNING
H315, H319, H335
P261, P280, P305+351+338
Harmful Xn
R-phrases R20/21/22, R36/37/38
S-phrases S26, S36/37
NFPA 704
Flammability code 0: Will not burn. E.g., water Health code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroform Reactivity code 1: Normally stable, but can become unstable at elevated temperatures and pressures. E.g., calcium Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 204 °C (399 °F; 477 K)
Lethal dose or concentration (LD, LC):
  • 355 mg/kg (oral, rat)[2]
  • 1180 mg/kg (dermal, rat)[2]
  • 1.6 mmol/kg(s.c., mouse)[4]
US health exposure limits (NIOSH):
PEL (Permissible)
none[3]
REL (Recommended)
0.6 ppm (10 mg/m3)[3]
IDLH (Immediate danger)
N.D.[3]
Related compounds
Related haloalkanes
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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.

Structure[edit]

The molecule adopts tetrahedral molecular geometry with C3v symmetry.

Synthesis and reactions[edit]

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;[5] and at much the same time independently by John Thomas Cooper.[6] 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).

Iodoform synthesis.svg

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.

Natural occurrence[edit]

Angel's bonnets contain iodoform and show its characteristic odor.

Applications[edit]

The compound finds small scale use as a disinfectant.[4][7] 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[edit]

References[edit]

  1. ^ 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. 
  2. ^ a b c d e f g Record in the GESTIS Substance Database of the IFA
  3. ^ a b c "NIOSH Pocket Guide to Chemical Hazards #0343". National Institute for Occupational Safety and Health (NIOSH). 
  4. ^ a b Merck Index, 12 Edition, 5054
  5. ^ 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 
  6. ^ James, Frank A. J. L. "Cooper, John Thomas (1790–1854), chemist". Oxford Dictionary of National Biography. Oxford University Press. Retrieved 26 January 2012. 
  7. ^ Lyday, Phyllis A. (2005), "Iodine and Iodine Compounds", Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim 

External links[edit]