N-Methyliminodiacetic acid

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N-Methyliminodiacetic acid is an organic compound with the formula CH3N(CH2CO2H)2. It is a white solid, which as its conjugate base CH3N(CH2CO2)2 is used as a chelating agent for iron.[2] It is a component of organoboron reagents as well.[3]

N-Methyliminodiacetic acid
Names
Other names
N-(Carboxymethyl)-N-methyl-glycine
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.022.326 Edit this at Wikidata
EC Number
  • 224-557-6
UNII
  • InChI=1S/C5H9NO4/c1-6(2-4(7)8)3-5(9)10/h2-3H2,1H3,(H,7,8)(H,9,10)
    Key: XWSGEVNYFYKXCP-UHFFFAOYSA-N
  • CN(CC(=O)O)CC(=O)O
Properties
C5H9NO4
Molar mass 147.130 g·mol−1
Appearance white solid
Melting point 223–225 °C (433–437 °F; 496–498 K)
Hazards
GHS labelling:[1]
GHS07: Exclamation mark
Warning
H315, H319, H335
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Synthesis and reaction

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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]

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References

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  1. ^ "N-Methyliminodiacetic acid". pubchem.ncbi.nlm.nih.gov.
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ "MIDA Boronates".
  6. ^ 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.