Sodium chloroacetate

Sodium chloroacetate

Names
Preferred IUPAC name Sodium chloroacetate
Other names sodium monochloroacetate
Identifiers
CAS Number	3926-62-3^Y
3D model (JSmol)	Interactive image
ChemSpider	56306^N
ECHA InfoCard	100.021.363
PubChem CID	23665759
UNII	8D9PZU6L69^Y
CompTox Dashboard (EPA)	DTXSID1027550
InChI InChI=1S/C2H3ClO2.Na/c3-1-2(4)5;/h1H2,(H,4,5);/q;+1/p-1^N Key: FDRCDNZGSXJAFP-UHFFFAOYSA-M^N InChI=1/C2H3ClO2.Na/c3-1-2(4)5;/h1H2,(H,4,5);/q;+1/p-1 Key: FDRCDNZGSXJAFP-REWHXWOFAF
SMILES C(C(=O)[O-])Cl.[Na+]
Properties
Chemical formula	C2H2ClNaO2
Molar mass	116.48 g·mol^−1
Appearance	white solid
Density	1.401 g/cm^3 (25 °C)
Solubility in water	soluble in water, ethanol, chloroform, ether and benzene
Hazards
Occupational safety and health (OHS/OSH):
Main hazards	irritant to skin
Autoignition temperature	does not ignite
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Sodium chloroacetate is the organic compound with the formula CH₂ClCO₂Na. A white, water-soluble solid, it is the sodium salt of chloroacetic acid. Many of its uses are similar to those of the parent acid. It is prepared by treating chloroacetic acid with sodium carbonate.^[1][2]

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 carboxymethylcellulose. 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 by reaction with sodium 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 series Organic Syntheses. With bifunctional nucleophiles, sodium chloroacetate is a precursor to heterocycles.^[4][5]

Reaction with sodium nitrite give nitroacetic acid.^[6] With sodium ethoxide it gives ethoxyacetate.^[7] With ethyl acetoacetate ethyl acetosuccinate is produced.^[8]

Hydrolysis gives glycolic acid.^[1]

References

1. Koenig, Günter; Lohmar, Elmar; Rupprich, Norbert (2000). "Chloroacetic Acids". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a06_537. ISBN 3527306730.
2. Nathan Weiner (1938). "Malonic Acid". Organic Syntheses. 18: 50. doi:10.15227/orgsyn.018.0050.
3. J. K. H. Inglis (1928). "Ethyl Cyanoacetate". Organic Syntheses. 8: 74. doi:10.15227/orgsyn.008.0074.
4. C. Ernst Redemann, Roland N. Icke, Gordon A. Alles (1947). "Rhodanine". Organic Syntheses. 27: 73. doi:10.15227/orgsyn.027.0073.
5. C. F. H. Allen, J. A. VanAllan (1947). "Pseudothiohydantoin". Organic Syntheses. 27: 71. doi:10.15227/orgsyn.027.0071.
6. F. C. Whitmore, Marion G. Whitmore (1923). "Nitromethane". Organic Syntheses. 3: 83. doi:10.15227/orgsyn.003.0083.
7. Reynold C. Fuson, Bruno H. Wojcik (1933). "Ethoxyacetic Acid and Ethyl Ethoxyacetate". Organic Syntheses. 13: 42. doi:10.15227/orgsyn.013.0042.
8. Homer Adkins, Neville Isbell, Bruno Wojcik (1934). "Ethyl Acetosuccinate". Organic Syntheses. 14: 38. doi:10.15227/orgsyn.014.0038.