Dichloroacetaldehyde is a chlorinated aldehyde with the chemical formula . Along with monochloroacetaldehyde and

trichloroacetaldehyde Chloral, also known as trichloroacetaldehyde or trichloroethanal, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a o ...

, it is one of the three possible chlorinated

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 ...

Properties and reactions

Dichloroacetaldehyde is a highly volatile liquid that is easily soluble in water to form Hydrates. A

geminal diol A geminal diol (or gem-diol for short) is any organic compound having two hydroxyl functional groups () bound to the same carbon atom. Geminal diols are a subclass of the diols, which in turn are a special class of alcohols. Most of the geminal ...

, also known as monohydrate, 2,2-dichloro-1,1-ethanediol, is formed in water. : Dichloroacetaldehyde reaction01

The compound decomposes when heated. In the presence of

Lewis acids A Lewis acid (named for the American physical chemist Gilbert N. Lewis) is a chemical species that contains an empty orbital which is capable of accepting an electron pair from a Lewis base to form a Lewis adduct. A Lewis base, then, is any sp ...

such as

antimony trichloride Antimony trichloride is the chemical compound with the formula SbCl3. It is a soft colorless solid with a pungent odor and was known to alchemists as butter of antimony. Preparation Antimony trichloride is prepared by reaction of chlorine with a ...

iron(III) chloride Iron(III) chloride describes the inorganic compounds with the formula (H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated f ...

, aluminum trichloride,

tin(IV) chloride Tin(IV) chloride, also known as tin tetrachloride or stannic chloride, is an inorganic compound of tin and chlorine with the formula SnCl4. It is a colorless hygroscopic liquid, which fumes on contact with air. It is used as a precursor to other ...

boron trifluoride Boron trifluoride is the inorganic compound with the formula . This pungent, colourless, and toxic gas forms white fumes in moist air. It is a useful Lewis acid and a versatile building block for other boron compounds. Structure and bonding The g ...

, the trimer hexachloro

paraldehyde Paraldehyde is the cyclic trimer (chemistry), trimer of acetaldehyde molecules. Formally, it is a derivative of 1,3,5-trioxane, with a methyl group substituted for a hydrogen atom at each carbon. The corresponding tetramer is metaldehyde. A colo ...

(2,4,6-tris(dichloromethyl)-1,3,5-trioxane) can be obtained. The trimer forms colourless crystals that melt at 131–132 °C. At the boiling point of 210–220 °C, dichloroacetaldehyde decomposes. : Dichloroacetaldehyde reaction02

Reduction with

lithium aluminium hydride Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula or . It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic synthe ...

gives dichloroethanol.

Uses

Dichloroacetaldehyde is used to produce other chemical compounds such as

mitotane Mitotane, sold under the brand name Lysodren, is a steroidogenesis inhibitor and cytostatic antineoplastic medication which is used in the treatment of adrenocortical carcinoma and Cushing's syndrome. It is a chemical derivative, derivative of ...

. Condensation with

chlorobenzene Chlorobenzene (abbreviated PhCl) is an aryl chloride and the simplest of the chlorobenzenes, consisting of a benzene ring substituted with one chlorine atom. Its chemical formula is C6H5Cl. This colorless, flammable liquid is a common solvent a ...

yields p,p′-dichloro-1,1-diphenyl-2,2-dichloroethane, which was previously used as an insecticide: :

Synthesis

Dichloroacetaldehyde can be obtained by chlorinating acetaldehyde or

. Hypochlorination of 1,2-dichloroethylene using chlorine and water produces pure dichloroacetaldehyde.Jira, R.; Kopp, E.; McKusick, B.C.; Röderer, G.; Bosch, A.; Fleischmann, G.: ''Chloroacetaldehydes'' in

Ullmann’s Encyclopedia of Industrial Chemistry ''Ullmann's Encyclopedia of Industrial Chemistry'' is a major reference work related to industrial chemistry by chemist Fritz Ullmann, first published in 1914, and exclusively in German as "Enzyklopädie der Technischen Chemie" until 1984. His ...

, 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, .

References

{{reflist Aldehydes Dichloromethyl compounds