Chloral

Chloral
IUPAC name

Trichloroethanal
Identifiers
CAS number 75-87-6 Y
ChemSpider 6167 Y
UNII FLI06WS32H Y
KEGG C14866 Y
Jmol-3D images Image 1
Properties
Molecular formula C2HCl3O
Molar mass 147.388 g/mol
Density 1.512 g/cm3 @ 20 °C
Melting point

−57.5 °C
Boiling point

97.8 °C
Solubility in water forms soluble hydrate
Solubility in ethanol miscible
Solubility in diethyl ether miscible
Solubility in chloroform miscible
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Chloral, also known as trichloroacetaldehyde, is the organic compound with the formula Cl3CCHO. This aldehyde is a colourless oily liquid that is soluble in a wide range of solvents. It reacts with water to form chloral hydrate, a once widely used sedative and hypnotic substance.

Contents

Production

Chloral can be produced by chlorination of ethanol, as reported in 1832 by Justus von Liebig.

Key reactions

Aside from its tendency to hydrate, chloral is most notable as a building block in the synthesis of DDT. For this purpose, chloral is treated with chlorobenzene in the presence of a catalytic amount of sulfuric acid:

Cl3CCHO + 2 C6H5Cl → Cl3CCH(C6H4Cl)2 + H2O

This reaction was described by Othmar Zeidler in 1874.[1]

Chloral is also used to form chloroform by treating it with sodium hydroxide.

References

  1. ^ Othmar Zeidler (1874). "Verbindungen von Chloral mit Brom- und Chlorbenzol". Berichte der deutschen chemischen Gesellschaft 7 (2): 1180–1181. doi:10.1002/cber.18740070278. 

See also