Sodium chloroacetate

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Sodium chloroacetate
Sodium chloroacetate.svg
Names
Preferred IUPAC name
Sodium chloroacetate
Other names
sodium monochloroacetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.021.363 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C2H3ClO2.Na/c3-1-2(4)5;/h1H2,(H,4,5);/q;+1/p-1 X mark.svgN
    Key: FDRCDNZGSXJAFP-UHFFFAOYSA-M X mark.svgN
  • InChI=1/C2H3ClO2.Na/c3-1-2(4)5;/h1H2,(H,4,5);/q;+1/p-1
    Key: FDRCDNZGSXJAFP-REWHXWOFAF
  • C(C(=O)[O-])Cl.[Na+]
Properties
C2H2ClNaO2
Molar mass 116.48 g·mol−1
Appearancewhite 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 their standard state (at 25 °C [77 °F], 100 kPa).
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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]

Related Research Articles

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In organic chemistry, a ketone is an organic compound with the structure R−C(=O)−R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group −C(=O)−. The simplest ketone is acetone, with the formula (CH3)2CO. Many ketones are of great importance in biology and industry. Examples include many sugars (ketoses), many steroids, and the solvent acetone.

<span class="mw-page-title-main">Chloroacetic acid</span> Chemical compound

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 are dichloroacetic acid and trichloroacetic acid.

<span class="mw-page-title-main">Malonic acid</span> Carboxylic acid with chemical formula CH2(COOH)2

Malonic acid is a dicarboxylic acid with structure CH2(COOH)2. The ionized form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's diethyl ester. The name originates from the Greek word μᾶλον (malon) meaning 'apple'.

<span class="mw-page-title-main">Diethyl malonate</span> Chemical compound

Diethyl malonate, also known as DEM, is the diethyl ester of malonic acid. It occurs naturally in grapes and strawberries as a colourless liquid with an apple-like odour, and is used in perfumes. It is also used to synthesize other compounds such as barbiturates, artificial flavourings, vitamin B1, and vitamin B6.

<span class="mw-page-title-main">Nitro compound</span> Organic compound containing an −NO₂ group

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<span class="mw-page-title-main">Cyanamide</span> Chemical compound featuring a nitrile group attached to an amino group

Cyanamide is an organic compound with the formula CN2H2. This white solid is widely used in agriculture and the production of pharmaceuticals and other organic compounds. It is also used as an alcohol-deterrent drug. The molecule features a nitrile group attached to an amino group. Derivatives of this compound are also referred to as cyanamides, the most common being calcium cyanamide (CaCN2).

<i>o</i>-Phenylenediamine Chemical compound

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<span class="mw-page-title-main">Benzyl cyanide</span> Chemical compound

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<span class="mw-page-title-main">Cyanoacetamide</span> Chemical compound

2-Cyanoacetamide is an organic compound. It is an acetic amide with a nitrile functional group.

<span class="mw-page-title-main">Cyanoacetic acid</span> Chemical compound

Cyanoacetic acid is an organic compound. It is a white, hygroscopic solid. The compound contains two functional groups, a nitrile (−C≡N) and a carboxylic acid. It is a precursor to cyanoacrylates, components of adhesives.

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<span class="mw-page-title-main">Ethyl cyanoacetate</span> Chemical compound

Ethyl cyanoacetate is an organic compound that contains a carboxylate ester and a nitrile. It is a colourless liquid with a pleasant odor. This material is useful as a starting material for synthesis due to its variety of functional groups and chemical reactivity.

<span class="mw-page-title-main">1,3-Cyclohexanedione</span> Chemical compound

1,3-Cyclohexanedione is an organic compound with the formula (CH2)4(CO)2. It is one of three isomeric cyclohexanediones. It is a colorless compound that occurs naturally. It is the substrate for cyclohexanedione hydrolase. The compound exists mainly as the enol tautomer.

<span class="mw-page-title-main">Diethyl oxomalonate</span> Chemical compound

Diethyl oxomalonate is the diethyl ester of mesoxalic acid (ketomalonic acid), the simplest oxodicarboxylic acid and thus the first member (n = 0) of a homologous series HOOC–CO–(CH2)n–COOH with the higher homologues oxalacetic acid (n = 1), α-ketoglutaric acid (n = 2) and α-ketoadipic acid (n = 3) (the latter a metabolite of the amino acid lysine). Diethyl oxomalonate reacts because of its highly polarized keto group as electrophile in addition reactions and is a highly active reactant in pericyclic reactions such as the Diels-Alder reactions, cycloadditions or ene reactions. At humid air, mesoxalic acid diethyl ester reacts with water to give diethyl mesoxalate hydrate and the green-yellow oil are spontaneously converted to white crystals.

Sodium <i>p</i>-toluenesulfonate Chemical compound

Sodium p-toluenesulfonate is an organic compound with the formula CH3C6H4SO3Na. It is white, water-soluble solid. It is produced by the neutralization toluenesulfonic acid with sodium hydroxide. It is also a common product from the reactions of sodium-based reagents with toluenesulfonates.

References

  1. 1 2 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  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.{{cite journal}}: CS1 maint: multiple names: authors list (link)