Dichloroacetaldehyde

Last updated
Dichloroacetaldehyde
Dichloro Acetaldehyde Structural Formula V1.svg
Names
IUPAC name
2,2-dichloroethanal
Other names
dichloroethanal
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.001.063 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-169-5
KEGG
PubChem CID
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
Hazards
GHS labelling:
GHS-pictogram-acid.svg GHS-pictogram-skull.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H301, H310, H314, H330, H335, H351, H400
P203, P260, P261, P262, P264, P264+P265, P270, P271, P273, P280, P284, P301+P316, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P318, P319, P320, P321, P330, P361+P364, P363, P391, P403+P233, P405, P501
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).

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

Contents

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]

Dichloroacetaldehyde reaction01.svg

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]

Dichloroacetaldehyde reaction02.svg

Reduction with lithium aluminium hydride gives dichloroethanol. [2]

Uses

Dichloroacetaldehyde is used to produce other chemical compounds such as mitotane. [3] Condensation with chlorobenzene yields p,p′-dichloro-1,1-diphenyl-2,2-dichloroethane, which was previously used as an insecticide: [1]

Synthesis Dichlorodiphenyldichloroethane.svg

Synthesis

Dichloroacetaldehyde can be obtained by chlorinating acetaldehyde or paraldehyde. Hypochlorination of 1,2-dichloroethylene using chlorine and water produces pure dichloroacetaldehyde. [1] [4]

Related Research Articles

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<span class="mw-page-title-main">Acyl halide</span> Oxoacid compound with an –OH group replaced by a halogen

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

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Chloroacetaldehyde is an organic compound with the formula ClCH2CHO. Like some related compounds, it is highly electrophilic reagent and a potentially dangerous alkylating agent. The compound is not normally encountered in the anhydrous form, but rather as the hemiacetal (ClCH2CH(OH))2O.

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

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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. Ullmann, Fritz (2000). Ullmann's Encyclopedia of Industrial Chemistry. Vol. 1 (6th ed.). Germany: Wiley. ISBN   9783527306732.
  4. NLM Hazardous Substances Data Bank entry for Dichloroacetaldehyde