2113. Chloroacetic Anhydride

Nomenclature

CAS number: 541-88-8
Chloroacetic acid 1,1′-anhydride; monochloroacetic acid anhydride; sym-dichloroacetic anhydride.
C4H4Cl2O3; mol wt 170.98.
C 28.10%, H 2.36%, Cl 41.47%, O 28.07%.

Description and references

Prepd by treating monochloroacetic acid in tetrahydrofuran with methoxyacetylene at 15° and distilling the mixture: Eglinton et al., J. Chem. Soc. 1954, 1860; by mixing monochloroacetic acid and HCN with 1,4-dioxane satd with HCl and fractionating the mixture: Krieble, Smellie, US 2390106 (1945); by heating chloroacetyl chloride with monochloroacetic acid in the presence of AlCl3: Strosacker, Schwegler, US 1713104 (1929 to Dow).

Chemical structure

Properties

Prisms from benzene; d420 1.5494; mp 46°. bp760 203°; bp116 163°; bp62 149°; bp24 126°; bp10 109-110°; bp0.05 118-120°. Freely sol in ether, chloroform; slightly sol in benzene, practically insol in cold ligroin.

Use

In N-acetylation of amino acids in alkaline soln; prepn of cellulose chloroacetates.