4917. Iminodiacetic Acid

Nomenclature

CAS number: 142-73-4
N-(Carboxymethyl)glycine; iminodiethanoic acid; diglycine; IDA.
C4H7NO4; mol wt 133.10.
C 36.10%, H 5.30%, N 10.52%, O 48.08%.

Description and references

Obtained from nitrilotriacetic acid, N(CH2COOH)3, by HCl-hydrolysis in a bomb tube: Schwarzenbach et al., Helv. Chim. Acta 28, 1133 (1945); by oxygenation in presence of palladium/carbon catalyst: Tetenbaum, Stone, Chem. Commun. 1970, 1699. Iminodiacetic acid and nitrilotriacetic acid are formed upon boiling chloroacetic acid with concd aq ammonia: Heintz, Ann. 149, 88 (1869). See also Martell, Bersworth, J. Org. Chem. 15, 46 (1950).

Chemical structure

Properties

Orthorhombic crystals, dec 247.5° (commercial grade, mp 220-250°). pKa1 2.98; pKa2 9.89. Forms salts with acids and bases. Soly in water at 5°: 2.43 g/100 ml. Practically insol in acetone, methanol, ether, benzene, carbon tetrachloride, heptane.

Derivative

Hydrochloride.

Nomenclature

CAS number: 2802-06-4
C4H7NO4.HCl; mol wt 169.56.
C 28.33%, H 4.76%, N 8.26%, O 37.74%, Cl 20.91%.

Properties

Crystals, dec 238-239°. Concd aq solns yield the free acid when adjusted to pH 2 with NaOH.

Derivative

Sodium salt monohydrate.

Nomenclature

CAS number: 6011-32-1
C4H6NNaO4.H2O; mol wt 173.10.
C 27.75%, H 4.66%, N 8.09%, Na 13.28%, O 46.21%.

Properties

Freely sol in water. Forms complexes with Mg, Ca, Ba.

Use

Has been suggested as intermediate in the manuf of surface active agents, complex salts, chelating agents.