When methyle ketone hangout with Iodine smells like hospital → Iodoform

What is it?

Iodoform is the organoiodine compound with the formula CHI3. A pale yellow, crystalline, volatile substance, it has a penetrating and distinctive odor. Sometimes it's odor is referred to as the smell of hospitals.

It is occasionally used as a disinfectant.

Also known as...

Tri-iodomethane
Carbon triiodide
Methyl triiodide

Properties

Molecular Weight: 393.732 g/mol

Melting Point: 119 °C

Boiling Point: 218 °C

Color: Yellow powder or crystals

Odor: Characteristic, disagreeable odor

Solubility: 7,8 g/100ml Ethanol, 100 mg/l Water

Synthesis

The synthesis of iodoform was first described by Georges-Simon Serullas in 1822.

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).

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.

Intresting Fact

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century it was used in medicine as a healing and antiseptic dressing for wounds and sores, although this use is now superseded by superior antiseptics.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.

Safety

Flammability (red): Materials that will not burn under typical fire conditions.

Health (blue): Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury.

Instability/reactivity (yellow): Normally stable, but can become unstable at elevated temperatures and pressures.

Natural occurrence

The angel's bonnet mushroom contains iodoform, and shows its characteristic odor.

1H NMR

Reference: wikipedia.com ~ pubchem.com ~ nmrdb.org

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