Malonic acid

Catalog	BBC141822
CAS	141-82-2
Structure
Description	The common technique for producing malonic acid is from chloroacetic acid.Malonic acid undergoes thermal decarboxylation at temperatures of 135-137oC.2
Synonyms	Propane-1,3-dioic acid
IUPAC Name	Propanedioic acid
Molecular Weight	104.06
Molecular Formula	C3H4O4
Canonical SMILES	C(C(=O)O)C(=O)O
InChI	InChI=1S/C3H4O4/c4-2(5)1-3(6)7/h1H2,(H,4,5)(H,6,7)
InChI Key	OFOBLEOULBTSOW-UHFFFAOYSA-N
Boiling Point	140 °C
Melting Point	132-135 °C(lit.)
Flash Point	157 °C
Purity	99%
Density	1.619 g/cm³ at 25 °C
Solubility	greater than or equal to 100 mg/mL at 72° F (NTP, 1992);7.33 M;In water, 6.23X10+5 mg/L at 25 °C;In water, 7.66X10+5 mg/L at 20 °C (pH 1-10), EU Guideline Method A.6 (flask method);One gram dissolves in: 0.65 mL water, about 2 mL alcohol, 1.1 mL methanol, 3 mL propyl alcohol, 13 mL ether, 7 mL pyridine;763.0 mg/mL;Solubility in water, g/100ml at 20 °C: 7.3
Appearance	White liquid
Application	Malonic acid serves a versatile purpose in various industries due to its unique chemical properties. This dicarboxylic acid is highly soluble in water and oxygenated solvents, with remarkable acidity, making it more acidic than acetic acid. In chemical synthesis, malonic acid is employed as a building block to introduce the -CH2-COOH group, notably through processes such as the Knoevenagel condensation. It is an essential intermediate in the synthesis of barbiturates and other pharmaceuticals and acts as a stabilizer in high-end cosmetics and pharmaceutical products. Malonic acid's decomposability into non-polluting byproducts like carbon dioxide and water makes it an eco-friendly option for aluminum surface treatments. Furthermore, it is utilized as a precursor for producing polyesters and alkyd resins in coating applications, offering protection against UV light, corrosion, and oxidation. Its capability to act as a cross-linker extends its applications to the creation of surgical adhesives and specialty chemicals, including flavors and fragrances. Through various reactions, such as condensing with urea to form barbituric acid or with acetone to form Meldrum's acid, malonic acid proves its indispensability in scientific and industrial domains.
Storage	Sealed in dry, room temperature
EC Number	205-503-0
pH	3.17 (1 mM solution)
pKa	2.83(at 25 °C)
Refractive Index	1.4780
Solubility in Water	1400 g/L
Vapor Pressure	0.00 mmHg;2.7X10-6 mm Hg at 23 °C