Chloroacetic acid

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Chloroacetic acid
IUPAC name Chloroacetic acid
Identifiers
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RTECS number AF8575000
Properties
C2H3ClO2
Molar mass 94.50 g mol−1
Appearance Colourless or white crystals
Density 1.58 g cm−3, solid
Melting point
Boiling point
Acidity (pKa) 2.82
Hazards
Main hazards alkylating agent
R-phrases 25-34-50
S-phrases 23-37-45-61
Flash point {{{value}}}
Related compounds
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Chloroacetic acid is the chemical compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. Like other chloroacetic acids and related halocarbons, it is a potentially dangerous alkylating agent.

Chloroacetic acid is synthesized by chlorinating of acetic acid in the presence of red phosphorus, sulfur, or iodine as a catalyst:

CH3CO2H + Cl2 → ClCH2CO2H + HCl

It also forms by the hydrolysis of trichloroethylene using sulfuric acid as a catalyst.

Illustrative of its usefulness in organic chemistry is the O-alkylation of salicylaldehyde with chloroacetic acid, followed by decarboxylation of the resulting ether, produces benzofuran.[1]

References

  1. Burgstahler, A. W.; Worden, L. R. (1966). "Coumarone." Org. Synth. 46: 28.

See also

External links

  • "Monochloroacetic Acid". Dow Chemical. Unknown parameter |accessdaymonth= ignored (help); Unknown parameter |accessyear= ignored (|access-date= suggested) (help)
  • "Monochloroacetic Acid". IPCS Inchem. Unknown parameter |accessdaymonth= ignored (help); Unknown parameter |accessyear= ignored (|access-date= suggested) (help)

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