Dichloroiodomethane

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Dichloroiodomethane
Dichloroiodomethane.png
Names
IUPAC name
dichloro(iodo)methane
Other names
DCIM, Chloriodoform (archaic), [1] IDCM, iododichloromethane
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/CHCl2I/c2-1(3)4/h1H
    Key: HNLZCOJXSLDGKD-UHFFFAOYSA-N
  • ClC(I)Cl
Properties
CHCl2I
Molar mass 210.82 g·mol−1
Appearancepale yellow liquid
Boiling point 131°C [2]
very slighlty
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Dichloroiodomethane (DCIM) is a trihalomethane with the chemical formula CHCl2I. It is a heavy, nonflammable, transparent pale yellow liquid with a chloroform-like odour. [1] DCIM is soluble in organic solvents like acetone, diethyl ether, ethanol and benzene. [2] It decomposes in contact with air and light. It has been detected in disinfected tap water and is considered to be a contaminant. [3] DCIM has an estimated half-life of 275 years in water. [4]

It was discovered by Georges-Simon Serullas in 1824, two years after his discovery of iodoform. [1]

Synthesis

Many synthesis routes are known. Reaction of chloroform with sodium iodide [5] or iodoethane [6] gives dichloroiodomethane. Older methods include distillation of iodoform with phosphorus pentachloride or mercuric chloride. [1]

Related Research Articles

Chloroform, or trichloromethane, is an organic compound with the formula CHCl3 and a common solvent. It is a very volatile, colorless, strong-smelling, dense liquid produced on a large scale as a precursor to refrigerants and PTFE. Chloroform is a trihalomethane that serves as a powerful anesthetic, euphoriant, anxiolytic, and sedative when inhaled or ingested. Chloroform was used as an anesthetic between the 19th century and the first half of the 20th century. It is miscible with many solvents but it is only very slightly soluble in water.

<span class="mw-page-title-main">Elimination reaction</span> Reaction where 2 substituents are removed from a molecule in a 1 or 2 step mechanism

An elimination reaction is a type of organic reaction in which two substituents are removed from a molecule in either a one- or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction. The numbers refer not to the number of steps in the mechanism, but rather to the kinetics of the reaction: E2 is bimolecular (second-order) while E1 is unimolecular (first-order). In cases where the molecule is able to stabilize an anion but possesses a poor leaving group, a third type of reaction, E1CB, exists. Finally, the pyrolysis of xanthate and acetate esters proceed through an "internal" elimination mechanism, the Ei mechanism.

<span class="mw-page-title-main">Iodoform</span> Chemical compound

Iodoform is the organoiodine compound with the chemical formula CHI3. It is a pale yellow, crystalline, volatile substance, with a penetrating and distinctive odor and, analogous to chloroform, sweetish taste. It is occasionally used as a disinfectant.

<span class="mw-page-title-main">Chlorine dioxide</span> Chemical compound

Chlorine dioxide is a chemical compound with the formula ClO2 that exists as yellowish-green gas above 11 °C, a reddish-brown liquid between 11 °C and −59 °C, and as bright orange crystals below −59 °C. It is usually handled as an aqueous solution. It is commonly used as a bleach. More recent developments have extended its applications in food processing and as a disinfectant.

<span class="mw-page-title-main">Bromoform</span> Chemical compound

Bromoform is an organic compound with the chemical formula CHBr3. It is a colorless liquid at room temperature, with a high refractive index and a very high density. Its sweet odor is similar to that of chloroform. It is one of the four haloforms, the others being fluoroform, chloroform, and iodoform. It is a brominated organic solvent. Currently its main use is as a laboratory reagent. It is very slightly soluble in water and is miscible with alcohol, benzene, chloroform, ether, petroleum ether, acetone and oils.

In chemistry, trihalomethanes (THMs) are chemical compounds in which three of the four hydrogen atoms of methane are replaced by halogen atoms. Trihalomethanes with all the same halogen atoms are called haloforms. Many trihalomethanes find uses in industry as solvents or refrigerants. Some THMs are also environmental pollutants, and few are considered carcinogenic.

<span class="mw-page-title-main">Sodium chlorite</span> Chemical compound

Sodium chlorite (NaClO2) is a chemical compound used in the manufacturing of paper and as a disinfectant.

Dichlorocarbene is the reactive intermediate with chemical formula CCl2. Although this chemical species has not been isolated, it is a common intermediate in organic chemistry, being generated from chloroform. This bent diamagnetic molecule rapidly inserts into other bonds.

Fluoroform, or trifluoromethane, is the chemical compound with the formula CHF3. It is a hydrofluorocarbon as well as being apart of the haloforms, a class of compounds with the formula CHX3 with C3v symmetry. Fluoroform is used in diverse applications in organic synthesis. It is not an ozone depleter but is a greenhouse gas.

Calcium hypochlorite is an inorganic compound with formula Ca(ClO)2. It is a white solid, although commercial samples appear yellow. It strongly smells of chlorine, owing to its slow decomposition in moist air. This compound is relatively stable as a solid and solution and has greater available chlorine than sodium hypochlorite. "Pure" samples have 99.2% active chlorine. Given common industrial purity, an active chlorine content of 65-70% is typical. It is the main active ingredient of commercial products called bleaching powder, used for water treatment and as a bleaching agent.

<span class="mw-page-title-main">Trihalide</span>

A trihalide in chemistry is an organohalide consisting of three halide atoms bonded to a single atom or compound. An example of a trihalide is chloroform.

Monochloramine, often called chloramine, is the chemical compound with the formula NH2Cl. Together with dichloramine (NHCl2) and nitrogen trichloride (NCl3), it is one of the three chloramines of ammonia. It is a colorless liquid at its melting point of −66 °C (−87 °F), but it is usually handled as a dilute aqueous solution, in which form it is sometimes used as a disinfectant. Chloramine is too unstable to have its boiling point measured.

<span class="mw-page-title-main">Bromodichloromethane</span> Chemical compound

Bromodichloromethane is a trihalomethane with formula CHBrCl2.

<span class="mw-page-title-main">Potassium thiocyanate</span> Chemical compound

Potassium thiocyanate is the chemical compound with the molecular formula KSCN. It is an important salt of the thiocyanate anion, one of the pseudohalides. The compound has a low melting point relative to most other inorganic salts.

Disinfection by-products (DBPs) are organic and inorganic compounds resulting from chemical reactions between organic and inorganic substances such as contaminates and chemical treatment disinfection agents, respectively, in water during water disinfection processes.

<span class="mw-page-title-main">Haloform reaction</span> Chemical reaction involving repeated halogenation of an acetyl group (–COCH3)

In chemistry, the haloform reaction is a chemical reaction in which a haloform is produced by the exhaustive halogenation of an acetyl group, in the presence of a base. The reaction can be used to transform acetyl groups into carboxyl groups or to produce chloroform, bromoform, or iodoform. Note that fluoroform can't be prepared in this way.

Performic acid (PFA) is an organic compound with the formula CH2O3. It is an unstable colorless liquid which can be produced by mixing formic acid with hydrogen peroxide. Owing to its oxidizing and disinfecting action, it is used in the chemical, medical and food industries.

<span class="mw-page-title-main">Trimethyl orthoformate</span> Chemical compound

Trimethyl orthoformate (TMOF) is the organic compound with the formula HC(OCH3)3. A colorless liquid, it is the simplest orthoester. It is a reagent used in organic synthesis for the formation of methyl ethers. The product of reaction of an aldehyde with trimethyl orthoformate is an acetal. In general cases, these acetals can be deprotected back to the aldehyde by using hydrochloric acid.

<span class="mw-page-title-main">Georges-Simon Serullas</span>

Georges-Simon Serullas was a French pharmacist. He was a professor of pharmacy notable for being the first to publish a work on Iodoform, an early antiseptic and disinfectant.

<span class="mw-page-title-main">Tetraiodoethylene</span> Chemical compound

Tetraiodoethylene (TIE), or diiodoform, is the periodinated analogue of ethylene with the chemical formula C2I4. It is a decomposition product of carbon tetraiodide and diiodoacetylene. It is an odourless yellow crystalline solid that is soluble in benzene and chloroform, and insoluble in water. It has been used as an antiseptic and a component in pesticide and fungicide formulations.

References

  1. 1 2 3 4 Leopold Gmelin, Henry Watts, Chloriodoform in Hand-book of Chemistry (1848), pages 337–339
  2. 1 2 D213 Dichloroiodomethane, The Dictionary of substances and their effects, p. 324
  3. Emma Goslan, Kenneth Clive Thompson, Simon Gillespie, Disinfection By-products in Drinking Water (2015), Royal Society of Chemistry
  4. Liu, David H. F; Liptak, Bela G, Groundwater and surface water pollution, page 57
  5. Determination of Dichloroiodomethane in Water (1996)
  6. Nariyoshi Kawabata, Masami Tanimoto, Shigehiro Fujiwara. Synthesis of monohalocyclopropane derivatives from olefins by the reaction with trihalomethanes and copper, Tetrahedron, 1979