Chloral

Chloral
IUPAC name	Trichloroethanal
Identifiers
CAS number	75-87-6 Y
SMILES	ClC(Cl)(Cl)C=O
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
Y (what is this?)  (verify) 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.

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]

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.