Chemical compound
N-Methyliminodiacetic acid is an organic compound with the formula CH3N(CH2CO2H)2. It is a white solid, which as its conjugate base CH3N(CH2CO−2)2 is used as a chelating agent for iron.[2] It is a component of organoboron reagents as well.[3]
Synthesis and reaction
It is prepared from imidodiacetic acid by N-methylation using the Eschweiler–Clarke reaction:[4]
MIDA boronates are derivatives with the formula CH3N(CH2CO2)2BR, where R is a cross-coupling partner.[5]
Related compounds
References
- ^ "N-Methyliminodiacetic acid". pubchem.ncbi.nlm.nih.gov.
- ^ Lovley, D. R.; Woodward, J. C.; Chapelle, F. H. (1996). "Rapid Anaerobic Benzene Oxidation with a Variety of Chelated Fe(III) Forms". Applied and Environmental Microbiology. 62 (1): 288–291. Bibcode:1996ApEnM..62..288L. doi:10.1128/aem.62.1.288-291.1996. PMC 1388759. PMID 16535218.
- ^ Dailey, Ian; Burke, Martin D. (2010). "N -(Carboxymethyl)- N -methyl-glycine". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rn01228.pub2. ISBN 978-0471936237.
- ^ Ballmer, Steven G.; Gillis, Eric P.; Burke, Martin D. (2009). "B-Protected Haloboronic Acids for Iterative Cross-Coupling". Organic Syntheses. 86: 344. doi:10.15227/orgsyn.086.0344.
- ^ "MIDA Boronates".
- ^ Hubregtse, Ton; Hanefeld, Ulf; Arends, Isabel W. C. E. (2007). "Stabilizing Factors for Vanadium(IV) in Amavadin". European Journal of Organic Chemistry. 2007 (15): 2413–2422. doi:10.1002/ejoc.200601053.
