Iodoform

Jump to: navigation, search
Template:Chembox ECNumberTemplate:Chembox E numberTemplate:Chembox SolubilityInWater
Iodoform
IUPAC name Iodoform
Other names Triiodomethane, Methyl triiodide, Carbon triiodide, TIM
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 879: attempt to index field 'wikibase' (a nil value).
KEGG
RTECS number PB7000000
Properties
CHI3
Molar mass 393.73 g/mol
Appearance Yellowish crystalls
Density 4.008 g/cm3
Melting point
Boiling point
log P 3.83
kH 0.34 mol.kg-1.bar-1
Structure
Crystal structure Hexagonal
Molecular shape Tetrahedral
Hazards
EU classification {{{value}}}
R-phrases R20/21/22, R36/37/38
S-phrases S22, S26, S36/37/39
Flash point {{{value}}}
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

WikiDoc Resources for Iodoform

Articles

Most recent articles on Iodoform

Most cited articles on Iodoform

Review articles on Iodoform

Articles on Iodoform in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Iodoform

Images of Iodoform

Photos of Iodoform

Podcasts & MP3s on Iodoform

Videos on Iodoform

Evidence Based Medicine

Cochrane Collaboration on Iodoform

Bandolier on Iodoform

TRIP on Iodoform

Clinical Trials

Ongoing Trials on Iodoform at Clinical Trials.gov

Trial results on Iodoform

Clinical Trials on Iodoform at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Iodoform

NICE Guidance on Iodoform

NHS PRODIGY Guidance

FDA on Iodoform

CDC on Iodoform

Books

Books on Iodoform

News

Iodoform in the news

Be alerted to news on Iodoform

News trends on Iodoform

Commentary

Blogs on Iodoform

Definitions

Definitions of Iodoform

Patient Resources / Community

Patient resources on Iodoform

Discussion groups on Iodoform

Patient Handouts on Iodoform

Directions to Hospitals Treating Iodoform

Risk calculators and risk factors for Iodoform

Healthcare Provider Resources

Symptoms of Iodoform

Causes & Risk Factors for Iodoform

Diagnostic studies for Iodoform

Treatment of Iodoform

Continuing Medical Education (CME)

CME Programs on Iodoform

International

Iodoform en Espanol

Iodoform en Francais

Business

Iodoform in the Marketplace

Patents on Iodoform

Experimental / Informatics

List of terms related to Iodoform

Overview

The compound iodoform is CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating odor (in older chemistry texts, the smell is sometimes referred to as the smell of hospitals) and, analogous to chloroform, sweetish taste. It is slightly soluble in glycerol, petroleum ether or alcohol (78 g/l at 25 °C), averagely soluble in chloroform, acetic acid and ether (136 g/l at 25 °C) and easily soluble in benzene and acetone (120 g/l at 25 °C).

Physical properties

Its entalphy of sublimation is 69.9 kJ.mol-1 at range of temperatures 35 - 92 °C.

Iodoform molecule parameters are: d(C-I) = 2.12 ± 0.04 Å, d(I-I) = 3.535 ± 0.01 Å and I-C-I = 113°. Dipole moment is 1 D. Its space group is P63 and lattice constants are a = 6.83 Å, c = 7.52 Å.

It has critical point at 584.85 °C, 5.63 MPa. Refractive index is 1.786 (D, 20 °C).

Synthesis

It was first prepared by Georges Serrulas in 1822 and its molecular formula was identified by Jean-Baptiste Dumas in 1834.

Iodoform can be synthesized in the haloform reaction by the reaction of iodine and sodium hydroxide with any one of these four kinds of organic compounds:

Iodoform synthesis.png

These reactions are so reliable that it is called the iodoform test, signalled by the precipitation of pale yellow crystals.

Reactions

Some reagents (e.g. hydroiodic acid) can convert iodoform to diiodomethane.

Also conversion to carbon dioxide is possible. Iodoform reacts with silver nitrate producing carbon monoxide, which is oxidized by mixture of sulfuric acid and iodine pentaoxide.

Uses

It was used in medicine as a healing and antiseptic dressing for wounds and sores around the beginning of the 20th century, though this use is now superseded by better antiseptics.

References

  • Merck Index, 12 Edition, 5054.

See also

External links


bg:Йодоформ cs:Jodoform de:Iodoform it:Iodoformio lv:Jodoforms hu:Jodoform