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Malonic acid



Malonic acid
IUPAC name propanedioic acid
Other names methanedicarboxylic acid
Identifiers
CAS number 141-82-2
SMILES O=C(O)CC(O)=O
Properties
Molecular formula C3H4O4
Molar mass 104.03 g/mol
Density 1,619 g/cm3, Solid
Melting point

135-136°C (408-409 K)

Boiling point

Decomposes

Solubility in water Completely Soluble
Hazards
MSDS External MSDS
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)

Infobox disclaimer and references

Malonic acid (IUPAC systematic name: propanedioic acid) is a dicarboxylic acid with structure CH2(COOH)2. The ionised form of malonic acid, as well as its esters and salts, are known as malonates. For example, diethyl malonate is malonic acid's ethyl ester. The name originates from Latin malum, meaning apple.

Additional recommended knowledge

Contents

Biochemistry

The calcium salt of malonic acid occurs in high concentrations in beetroot. It exists in its normal state as white crystals.

Organic synthesis

A classical preparation of malonic acid starts from acetic acid[1]. This acid is chlorinated to chloroacetic acid. Sodium carbonate generates the sodium salt which is then reacted with sodium cyanide to the cyano acetic acid salt in a nucleophilic substitution. The nitrile group can be hydrolysed with sodium hydroxide to sodium malonate and acidification affords malonic acid.

Organic reactions

In a well known reaction malonic acid condenses with urea to barbituric acid. Malonic acid is frequently used as an enolate in Knoevenagel condensations or condensed with acetone to form Meldrum's acid. Its esters are also used for the -CH2COOH synthon in the malonic ester synthesis.

References

  1. ^ Nathan Weiner. "Malonic acid". Org. Synth.; Coll. Vol. 2: 376. 
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Malonic_acid". A list of authors is available in Wikipedia.
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