Dichloroacetaldehyde
Names
IUPAC name
2,2-dichloroethanal
Other names
dichloroethanal
Identifiers
3D model (JSmol)
ChEBI
ECHA InfoCard 100.001.063
EC Number
  • 201-169-5
KEGG
UNII
UN number 1993
  • InChI=1S/C2H2Cl2O/c3-2(4)1-5/h1-2H
    Key: NWQWQKUXRJYXFH-UHFFFAOYSA-N
  • C(=O)C(Cl)Cl
Properties
C2H2Cl2O
Molar mass 112.94 g·mol−1
Density 1.4 g/mL
Melting point −50 °C (−58 °F; 223 K)
Boiling point 88 °C (190 °F; 361 K)
forms hydrate
Related compounds
Related compounds
 chloroacetaldehyde, trichloroacetaldehyde
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Dichloroacetaldehyde is a chlorinated aldehyde with the chemical formula HCCl2CHO. Along with monochloroacetaldehyde and trichloroacetaldehyde, it is one of the three possible chlorinated acetaldehydes.

Properties and reactions

Dichloroacetaldehyde is a highly volatile liquid that is easily soluble in water to form Hydrates. A geminal diol, also known as monohydrate, 2,2-dichloro-1,1-ethanediol, is formed in water.[1]

Hydration of the aldehyde

The compound decomposes when heated. In the presence of Lewis acids such as antimony trichloride, iron(III) chloride, aluminum trichloride, tin(IV) chloride or boron trifluoride, the trimer hexachloroparaldehyde (2,4,6-tris(dichloromethyl)-1,3,5-trioxane) can be obtained.[1] The trimer forms colourless crystals that melt at 131–132 °C. At the boiling point of 210–220 °C, dichloroacetaldehyde decomposes.[1]

Formation of hexachloroparaldehyde

Reduction with lithium aluminium hydride gives dichloroethanol.[2]

Uses

Dichloroacetaldehyde is used to produce other chemical compounds such as mitotane. Condensation with chlorobenzene yields p,p′-dichloro-1,1-diphenyl-2,2-dichloroethane, which was previously used as an insecticide:[1]

Synthesis

Dichloroacetaldehyde can be obtained by chlorinating acetaldehyde or paraldehyde. Hypochlorination of 1,2-dichloroethylene using chlorine and water produces pure dichloroacetaldehyde.[1][3]

References

  1. 1 2 3 4 5 Jira, R.; Kopp, E.; McKusick, B.C.; Röderer, G.; Bosch, A.; Fleischmann, G.: Chloroacetaldehydes in Ullmann’s Encyclopedia of Industrial Chemistry, 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, doi:10.1002/14356007.a06_527.pub2.
  2. ↑ Sroog, C. E.; Woodburn, H. M. (1952). "2,2-Dichloroethanol". Organic Syntheses. 32: 46. doi:10.15227/orgsyn.032.0046.
  3. ↑ NLM Hazardous Substances Data Bank entry for Dichloroacetaldehyde
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