Iodoform

Structural formula
General
Surname	Iodoform
other names	Iodoform; Triiodomethane; Formyl triiodide; IODOFORM ( INCI ) ;
Molecular formula	CHI 3
Brief description	yellow, shiny leaves, hexagonal tablets or lemon-yellow, fine powder with a saffron-like odor
External identifiers / databases
EC number	200-874-5
ECHA InfoCard	100,000,795
PubChem	6374
ChemSpider	6134
DrugBank	DB13813
Wikidata	Q412393
Drug information
ATC code	D09 AA13
properties
Molar mass	393.73 g mol −1
Physical state	firmly
density	4.008 g cm −3 (20 ° C)
Melting point	119 ° C
boiling point	218 ° C
solubility	poor in water (0.1 g l −1 at 25 ° C); bad in fatty oils and glycerin ; good in chloroform , diethyl ether, and carbon disulfide ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302 + 312 + 332-315-319-335
	P: 261-280-305 + 351 + 338
MAK	Austria: 3 mg m −3 ; Switzerland: 0.6 ml m −3 or 10 mg m −3 ;
Toxicological data	355 mg kg −1 ( LD 50 , rat , oral )
Thermodynamic properties
ΔH f 0	181.1 ± 1.0 kJ mol −1
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Iodoform, sublimed

Iodoform ( empirical formula CHI ₃ ) is a yellow, saffron-like smelling chemical compound made of carbon , hydrogen and iodine and a simple halogenated hydrocarbon .

Due to its structure (CHX ₃ ) it is homologous to fluoroform , chloroform and bromoform and named analogously.

According to Fieser & Fieser, iodoform, together with tetraiodomethane, is the only colored organic compound without an unsaturated structural element.

history

Georges Serrulas first produced iodoform in 1822, Jean Baptiste Dumas established the empirical formula in 1834.

Extraction and presentation

Iodoform can be obtained from compounds with a CH ₃ CHOH group or CH ₃ CO group such as ethanol or acetone using Lugol's solution . The iodoform sample makes use of this reaction , with which the groups mentioned can be detected. For this purpose, for example, ethanol is dissolved in sodium hydroxide solution and Lugol's solution is added.

The exact mechanism for the preparation of iodoform from ethanol or acetone is similar to the mechanism of the haloform reaction .

During the synthesis of iodofom from ethanol ( 1 ), iodoform ( 4b ) is finally formed via the intermediate stages acetaldehyde ( 2 ), triiodoacetaldehyde ( 3 ) and the carbanion of iodoform ( 4a ).

Iodoform can also be made by electrolysis from a warm solution of potassium iodide , sodium carbonate and ethanol in water .

use

It is used for Takai olefination .

Medical use

In the past, iodoform (iodoform ether) dissolved in diethyl ether was used in dental medicine to disinfect wounds, as it releases a small, disinfecting amount of iodine with the moisture in the wound. At the same time, it also dried the wound, stopped minor bleeding and reduced the pain in the wound. Because of its characteristically intense odor, its high price and its harmfulness at high doses, iodoform is hardly used any more medically. Iodoform is still used very often in dentistry - it is the standard disinfectant for wound dressing using gauze strips and is used as a filling paste (with calcium hydroxide ) in the milk root filling .

Individual evidence

↑ entry to iodoform in CosIng database of the European Commission, accessed on 30 June 2020th
↑ ^a ^b ^c ^d ^e entry on iodoform. In: Römpp Online . Georg Thieme Verlag, accessed on March 3, 2014.
↑ ^a ^b ^c ^d ^e ^f Entry on triiodomethane in the GESTIS substance database of the IFA , accessed on February 29, 2020(JavaScript required) .
↑ Appendix I List of substances, MAK values and TRK values , 2007.
↑ Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 75-47-8 or Iodoform ), accessed on November 2, 2015.
↑ AS Carson, PG Laye, JB Pedley, Alison M. Welsby: The enthalpies of formation of iodomethane, diiodomethane, triiodomethane, and tetraiodomethane by rotating combustion calorimetry , in: The Journal of Chemical Thermodynamics , 1993 , 25 (2) , p. 261-269; doi : 10.1006 / jcht.1993.1025 .
^ Fieser, M. Fieser: Organische Chemie , 2nd edition, Verlag Chemie, Weinheim 1979, pp. 404-405.

Web links

Iodoform data sheet from Sigma-Aldrich , accessed on April 5, 2011 ( PDF ).

[CosIng-1] try to iodoform in CosIng database of the European Commission, accessed on 30 June 2020th

[roempp-2] ↑ ^a ^b ^c ^d ^e entry on iodoform. In: Römpp Online . Georg Thieme Verlag, accessed on March 3, 2014.

[GESTIS-3] ↑ ^a ^b ^c ^d ^e ^f Entry on triiodomethane in the GESTIS substance database of the IFA , accessed on February 29, 2020(JavaScript required) .

[4] Appendix I List of substances, MAK values and TRK values , 2007.

[5] Swiss Accident Insurance Fund (Suva): Limit values - current MAK and BAT values (search for 75-47-8 or Iodoform ), accessed on November 2, 2015.

[6] AS Carson, PG Laye, JB Pedley, Alison M. Welsby: The enthalpies of formation of iodomethane, diiodomethane, triiodomethane, and tetraiodomethane by rotating combustion calorimetry , in: The Journal of Chemical Thermodynamics , 1993 , 25 (2) , p. 261-269; doi : 10.1006 / jcht.1993.1025 .

[7] Fieser, M. Fieser: Organische Chemie , 2nd edition, Verlag Chemie, Weinheim 1979, pp. 404-405.