Sodium chloroacetate is the

organic compound In chemistry, organic compounds are generally any chemical compounds that contain carbon- hydrogen or carbon-carbon bonds. Due to carbon's ability to catenate (form chains with other carbon atoms), millions of organic compounds are known. Th ...

with the formula CH₂ClCO₂Na. A white, water-soluble solid, it is the

sodium Sodium is a chemical element with the symbol Na (from Latin ''natrium'') and atomic number 11. It is a soft, silvery-white, highly reactive metal. Sodium is an alkali metal, being in group 1 of the periodic table. Its only stable ...

salt Salt is a mineral composed primarily of sodium chloride (NaCl), a chemical compound belonging to the larger class of salts; salt in the form of a natural crystalline mineral is known as rock salt or halite. Salt is present in vast quanti ...

chloroacetic acid Chloroacetic acid, industrially known as monochloroacetic acid (MCA), is the organochlorine compound with the formula ClCH2CO2H. This carboxylic acid is a useful building block in organic synthesis. It is a colorless solid. Related compounds a ...

. Many of its uses are similar to those of the parent acid. It is prepared by treating chloroacetic acid with sodium carbonate.

Uses

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

cellulose acetate In biochemistry, cellulose acetate refers to any acetate ester of cellulose, usually cellulose diacetate. It was first prepared in 1865. A bioplastic, cellulose acetate is used as a film base in photography, as a component in some coatings, ...

. It is a precursor to many herbicides dimethoate and benazoline (the salt itself is also used as a contact herbicide). It is a precursor to

thioglycolic acid Thioglycolic acid (TGA) is the organic compound HSCH2CO2H. TGA is often called mercaptoacetic acid (MAA). It contains both a thiol (mercaptan) and carboxylic acid functional groups. It is a colorless liquid with a strongly unpleasant odor. TGA ...

by reaction with

sodium hydrosulfide Sodium hydrosulfide is the chemical compound with the formula NaHS. This compound is the product of the half-neutralization of hydrogen sulfide () with sodium hydroxide (NaOH). NaSH and sodium sulfide are used industrially, often for similar purpos ...

. Reaction with cyanide salts gives cyanoacetate NCCH₂CO₂Na. 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 series ''

Organic Syntheses ''Organic Syntheses'' is a peer-reviewed scientific journal that was established in 1921. It publishes detailed and checked procedures for the synthesis of organic compounds. A unique feature of the review process is that all of the data and exper ...

''. With bifunctional nucleophiles, sodium chloroacetate is a precursor to heterocycles. Reaction with

sodium nitrite Sodium nitrite is an inorganic compound with the chemical formula NaNO2. It is a white to slightly yellowish crystalline powder that is very soluble in water and is hygroscopic. From an industrial perspective, it is the most important nitrite ...

give nitroacetic acid. With

sodium ethoxide Sodium ethoxide, also referred to as sodium ethylate, is the ionic, organic compound with the formula , or NaOEt (Et = ethane). It is a white solid, although impure samples appear yellow or brown. It dissolves in polar solvents such as ethanol. ...

it gives ethoxyacetate. With ethyl acetoacetate ethyl acetosuccinate is produced. Hydrolysis gives

glycolic acid Glycolic acid (or hydroxyacetic acid; chemical formula HOCH2CO2H) is a colorless, odorless and hygroscopic crystalline solid, highly soluble in water. It is used in various skin-care products. Glycolic acid is widespread in nature. A glycolate ( ...

References

Acetates Organochlorides Organic sodium salts {{organic-compound-stub