Malonic acid

Malonic acid

Propanedioic acid;Malonic acid;Carboxyacetic acid;Dicarboxymethane;Methanedicarboxylic acid;1,3-Propanedioic acid;NSC 8124;Malonates;211863-95-5

141-82-2

C3H4O4

InChIKey=OFOBLEOULBTSOW-UHFFFAOYSA-N

104.06100

104.06

205-503-0

9KX7ZMG0MK

1085

8124

DTXSID7021659

White crystals|Crystalline powder|Colorless hygroscopic solid which sublimes in vacuum

2917190090

Bulk Drug Intermediates

74.60000

-0.8

Malonic acid appears as white crystals or crystalline powder. Sublimes in vacuum. (NTP, 1992)

1.6 g/cm³

135 °C (decomp)

215 °C @ Press: 14 Torr

201.9ºC

1.479

H2O: 1400 g/L (20 ºC)

Store at RT.

4.66E-07mmHg at 25°C

2.85(at 25 °C)

2.85 (at 25 °C)|pKa1 = 2.8, pKa2 = 5.7 at 25 °C

Enthalpy of Sublimation: 72.7 kJ/mol at 306 deg K, 108.0 kJ/mol at 348 deg K|Henry's Law constant = 4.8X10-13 atm-cu m/mole at 23 °C (estimated from vapor pressure and water solubility)|Hydroxyl radical reaction rate constant = 1.6X10-12 cu-cm/molc sec at 25 °C (est)

Water soluble.

Acids, Carboxylic

MALONIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions This chemical is incompatible with strong oxidizers. It is also incompatible with bases and reducing agents. (NTP, 1992)

Molar heat of combustion: 864 kJ/mol

92 kJ/mol

Critical temperature: 805 K (estimated); critical pressure: 5640 kPa (estimated)