Iodoform (also known as triiodomethane) is the

organoiodine compound Organoiodine chemistry is the study of the synthesis and properties of organoiodine compounds, or organoiodides, organic compounds that contain one or more carbon–iodine bonds. They occur widely in organic chemistry, but are relatively rare ...

with the

chemical formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as pare ...

. It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive 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 Chloroform, or trichloromethane (often abbreviated as TCM), is an organochloride with the formula and a common solvent. It is a volatile, colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to refrigerants and po ...

, sweetish taste. It is occasionally used as a

disinfectant A disinfectant is a chemical substance or compound used to inactivate or destroy microorganisms on inert surfaces. Disinfection does not necessarily kill all microorganisms, especially resistant bacterial spores; it is less effective than ...

Naming

The name iodoform originates with the "formyle radical," an archaic term for the HC moiety, and is retained for historical consistency. A full, modern name is triiodomethane. Another possible name is "carbon hydride triiodide". The "hydride" in the latter is sometimes omitted, though the IUPAC recommends against doing so, as "carbon triiodide" could also mean ( hexaiodoethane, a highly unstable compound).

Structure

The molecule adopts a tetrahedral geometry with C_3v

symmetry Symmetry () in everyday life refers to a sense of harmonious and beautiful proportion and balance. In mathematics, the term has a more precise definition and is usually used to refer to an object that is Invariant (mathematics), invariant und ...

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; and at much the same time independently by John Thomas Cooper. 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 In organic chemistry, a ketone is an organic compound with the structure , where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group (a carbon-oxygen double bond C=O). The simplest ketone is acetone ( ...

(),

acetaldehyde Acetaldehyde (IUPAC systematic name ethanal) is an organic compound, organic chemical compound with the chemical formula, formula , sometimes abbreviated as . It is a colorless liquid or gas, boiling near room temperature. It is one of the most ...

(),

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

(), and certain secondary

alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...

s (, where R is an alkyl or aryl group). : The reaction of iodine and base with

methyl In organic chemistry, a methyl group is an alkyl derived from methane, containing one carbon atom bonded to three hydrogen atoms, having chemical formula (whereas normal methane has the formula ). In formulas, the group is often abbreviated as ...

s 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 alcohol In chemistry, an alcohol (), is a type of organic compound that carries at least one hydroxyl () functional group bound to a Saturated and unsaturated compounds, saturated carbon atom. Alcohols range from the simple, like methanol and ethanol ...

s containing at least one

group in alpha-position. Some reagents (e.g.

hydrogen iodide Hydrogen iodide (HI) is a diatomic molecule and hydrogen halide. Aqueous solutions of HI are known as hydroiodic acid or hydriodic acid, a strong acid. Hydrogen iodide and hydroiodic acid are, however, different in that the former is a gas und ...

) convert iodoform to

diiodomethane Diiodomethane or methylene iodide, commonly abbreviated "MI", is an organoiodine compound. Diiodomethane is a very dense colorless liquid; however, it decomposes upon exposure to light liberating iodine, which colours samples brownish. It is slig ...

. Conversion to

carbon dioxide Carbon dioxide is a chemical compound with the chemical formula . It is made up of molecules that each have one carbon atom covalent bond, covalently double bonded to two oxygen atoms. It is found in a gas state at room temperature and at norma ...

is also possible. Iodoform reacts with aqueous

silver nitrate Silver nitrate is an inorganic compound with chemical formula . It is a versatile precursor to many other silver compounds, such as those used in photography. It is far less sensitive to light than the halides. It was once called ''lunar causti ...

to produce

carbon monoxide Carbon monoxide (chemical formula CO) is a poisonous, flammable gas that is colorless, odorless, tasteless, and slightly less dense than air. Carbon monoxide consists of one carbon atom and one oxygen atom connected by a triple bond. It is the si ...

. When treated with powdered elemental silver the iodoform is reduced, producing

acetylene Acetylene (Chemical nomenclature, systematic name: ethyne) is a chemical compound with the formula and structure . It is a hydrocarbon and the simplest alkyne. This colorless gas is widely used as a fuel and a chemical building block. It is u ...

. 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. 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 superior

antiseptic An antiseptic ( and ) is an antimicrobial substance or compound that is applied to living tissue to reduce the possibility of sepsis, infection, or putrefaction. Antiseptics are generally distinguished from ''antibiotics'' by the latter's abil ...

s, it is still used in

otolaryngology Otorhinolaryngology ( , abbreviated ORL and also known as otolaryngology, otolaryngology–head and neck surgery (ORL–H&N or OHNS), or ear, nose, and throat (ENT)) is a surgical subspecialty within medicine that deals with the surgical an ...

in the form of bismuth subnitrate iodoform paraffin paste (BIPP) as an antiseptic packing for cavities. It is the active ingredient in many ear powders for

dog The dog (''Canis familiaris'' or ''Canis lupus familiaris'') is a domesticated descendant of the gray wolf. Also called the domestic dog, it was selectively bred from a population of wolves during the Late Pleistocene by hunter-gatherers. ...

s and

cat The cat (''Felis catus''), also referred to as the domestic cat or house cat, is a small domesticated carnivorous mammal. It is the only domesticated species of the family Felidae. Advances in archaeology and genetics have shown that the ...

s, along with

zinc oxide Zinc oxide is an inorganic compound with the Chemical formula, formula . It is a white powder which is insoluble in water. ZnO is used as an additive in numerous materials and products including cosmetics, Zinc metabolism, food supplements, rubbe ...

and

propionic acid Propionic acid (, from the Greek language, Greek words πρῶτος : ''prōtos'', meaning "first", and πίων : ''píōn'', meaning "fat"; also known as propanoic acid) is a naturally occurring carboxylic acid with chemical formula . It is a ...

, which are used to prevent infection and facilitate removal of ear hair.

References

External links

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Preparation
* {{Authority control Iodoalkanes Halomethanes Antiseptics Iodine-containing natural products Organoiodides