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Open Access Articles- Top Results for Chloral

Chloral

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Chloral

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IUPAC name
Trichloroethanal
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75-87-6 7pxY ChemSpider 6167 7pxY EC number 200-911-5 Jmol-3D images Image KEGG C14866 7pxY PubChem Template:Chembox PubChem/format Template:Chembox UNII colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Properties

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C2HCl3O Molar mass 147.388 g/mol Appearance colorless, mobile, oily liquid Odor pungent and irritating Density 1.404 g/cm3 Melting point Script error: No such module "convert". Boiling point Script error: No such module "convert". forms soluble hydrate Solubility in ethanol miscible Solubility in diethyl ether miscible Solubility in chloroform miscible Acidity (pKa) 9.66 1.45572 colspan=2 style="background:#f8eaba; border-top:2px solid transparent; border-bottom:2px solid transparent; text-align:center;" #REDIRECTmw:Help:Magic words#Other
This page is a soft redirect. Hazards

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480 mg/kg (rat, oral)
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 is produced commercially by the chlorination of acetaldehyde in hydrochloric acid, producing chloral hydrate. Ethanol can also be used as a feedstock. This reaction is catalyzed by antimony trichloride:

H3CCHO + 3 Cl2 + H2O → Cl3CCH(OH)2 + 3 HCl

The chloral hydrate is distilled from the reaction mixture. The distillate is then dehydrated with concentrated sulfuric acid, after which the heavier acid layer (containing the water) is drawn off:

Cl3CCH(OH)2 → Cl3CCHO + H2O

The resulting product is purified by fractional distillation.[1] Small amounts of chloral hydrate occur in some chlorinated water.

Key reactions

Chloral tends to form adducts with water (to give chloral hydrate) and alcohols.

Aside from its tendency to hydrate, chloral is 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.[2] The related herbicide methoxychlor is also produced from chloral.

Treating chloral with sodium hydroxide gives chloroform and sodium formate

Cl3CCHO + NaOH → Cl3CH + HCOONa

Chloral is easily reduced to trichlorethanol, which is produced in the body from chloral.[1]

Safety

Chloral and chloral hydrate have the same properties biologically since the former hydrates rapidly. Chloral hydrate was routinely administered to patients on the gram scale with no lasting effects. Prolonged exposure to the vapors is unhealthy however, with a LC50 for 4-h exposure of 440 mg/m3.[1]

See also

References

  1. 1.0 1.1 1.2 Reinhard Jira, Erwin Kopp, Blaine C. McKusick, Gerhard Röderer, Axel Bosch and Gerald Fleischmann "Chloroacetaldehydes" in Ullmann's Encyclopedia of Industrial Chemistry, 2007, Wiley-VCH, Weinheim. doi:10.1002/14356007.a06_527.pub2
  2. Othmar Zeidler (1874). "Verbindungen von Chloral mit Brom- und Chlorbenzol". Berichte der deutschen chemischen Gesellschaft 7 (2): 1180–1181. doi:10.1002/cber.18740070278. 


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