N-Methyliminodiacetic acid explained

N-Methyliminodiacetic acid is an organic compound with the formula . It is a white solid, which as its conjugate base is used as a chelating agent for iron.^[1] It is a component of organoboron reagents as well.^[2]

Synthesis and reaction

It is prepared from imidodiacetic acid by N-methylation using the Eschweiler–Clarke reaction:^[3]

MIDA boronates are derivatives with the formula, where R is a cross-coupling partner.^[4]

Related compounds

• Imidodiacetic acid (IDA)
• N-(2-Carboxyethyl)iminodiacetic acid
• Nitrilotriacetic acid (NTA)
• N-Hydroxyiminodiacetic acid (HIDA), (registry number = 87339–38–6).^[5] See HIDA scan.

References

1. 10.1128/aem.62.1.288-291.1996 . Rapid Anaerobic Benzene Oxidation with a Variety of Chelated Fe(III) Forms . 1996 . Lovley . D. R. . Woodward . J. C. . Chapelle . F. H. . Applied and Environmental Microbiology . 62 . 1 . 288–291 . 16535218 . 1388759 . 1996ApEnM..62..288L .
2. Book: 10.1002/047084289X.rn01228.pub2 . N -(Carboxymethyl)- N -methyl-glycine . Encyclopedia of Reagents for Organic Synthesis . 2010 . Dailey . Ian . Burke . Martin D. . 978-0471936237 .
3. 10.15227/orgsyn.086.0344 . B-Protected Haloboronic Acids for Iterative Cross-Coupling . Organic Syntheses . 2009 . 86 . 344. Steven G. . Ballmer. Eric P. . Gillis. Martin D.. Burke . free .
4. Web site: MIDA Boronates .
5. 10.1002/ejoc.200601053 . Stabilizing Factors for Vanadium(IV) in Amavadin . 2007 . Hubregtse . Ton . Hanefeld . Ulf . Arends . Isabel W. C. E. . European Journal of Organic Chemistry . 2007 . 15 . 2413–2422 .