Chloral
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| Names | |||
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| IUPAC name
Trichloroethanal
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| Identifiers | |||
3D model (JSmol)
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| ChemSpider | |||
| ECHA InfoCard | 100.000.829 | ||
| KEGG | |||
| UNII | |||
CompTox Dashboard (EPA)
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| Properties | |||
| C2HCl3O | |||
| Molar mass | 147.388 g/mol | ||
| Density | 1.512 g/cm3 @ 20 °C | ||
| Melting point | −57.5 °C | ||
| Boiling point | 97.8 °C | ||
| forms soluble hydrate | |||
| Solubility in ethanol | miscible | ||
| Solubility in diethyl ether | miscible | ||
| Solubility in chloroform | miscible | ||
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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]
Chloral is also used to form chloroform by treating it with sodium hydroxide.
References
- ^ Othmar Zeidler (1874). "Verbindungen von Chloral mit Brom- und Chlorbenzol". Berichte der deutschen chemischen Gesellschaft. 7 (2): 1180–1181. doi:10.1002/cber.18740070278.