 | |
| Names | |
|---|---|
| Preferred IUPAC name Sodium chloroacetate | |
| Other names sodium monochloroacetate | |
| Identifiers | |
3D model (JSmol) | |
| ChemSpider |
|
| ECHA InfoCard | 100.021.363 |
| UNII | |
| |
| |
| Properties | |
| C2H2ClNaO2 | |
| Molar mass | 116.48 g·mol−1 |
| Appearance | white solid |
| Density | 1.401 g/cm3 (25 °C) |
| soluble in water, ethanol, chloroform, ether and benzene | |
| Hazards | |
| Occupational safety and health (OHS/OSH): | |
Main hazards | irritant to skin |
| does not ignite | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Sodium chloroacetate is theorganic compound with the formula CH2ClCO2Na. A white, water-soluble solid, it is thesodiumsalt ofchloroacetic acid. Many of its uses are similar to those of the parent acid. It is prepared by treating chloroacetic acid withsodium carbonate.[1][2]
Chloroacetate is a good alkylating agent, serving as a reagent for affixing the -CH2CO2− group to a wide variety of even weak nucleophiles.
In terms of practical, commercial uses, it is used to convert cellulose to carboxymethylcellulose. It is a precursor to many herbicidesdimethoate and benazoline (the salt itself is also used as a contactherbicide). It is a precursor tothioglycolic acid by reaction withsodium hydrosulfide. Reaction with cyanide salts gives cyanoacetate NCCH2CO2Na.[3] Cyanoacetate is a precursor to malonic acid.
Sodium chloroacetate is a common laboratory reagent in organic chemistry as illustrated by many entries in the book seriesOrganic Syntheses. With bifunctional nucleophiles, sodium chloroacetate is a precursor to heterocycles.[4][5]
Reaction withsodium nitrite givenitroacetic acid.[6] Withsodium ethoxide it gives ethoxyacetate.[7] With ethyl acetoacetate ethyl acetosuccinate is produced.[8]
Hydrolysis givesglycolic acid.[1]
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