N-Methyliminodiacetic acid

N-Methyliminodiacetic acid
Names
	Other names N-(Carboxymethyl)-N-methyl-glycine
Identifiers
CAS Number	4408-64-4 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1741474;
ChemSpider	19251;
ECHA InfoCard	100.022.326
EC Number	224-557-6;
PubChem CID	20441;
UNII	SH1YP5H4NA;
CompTox Dashboard (EPA)	DTXSID00196033 ;
	InChI 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;
	SMILES CN(CC(=O)O)CC(=O)O;
Properties
Chemical formula	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:
Pictograms
Signal word	Warning
Hazard statements	H315, H319, H335
Precautionary statements	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). Infobox references

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

Imidodiacetic acid (IDA)
N-(2-Carboxyethyl)iminodiacetic acid
Nitrilotriacetic acid (NTA)
N-Hydroxyiminodiacetic acid (HIDA), HON(CH₂CO₂H)₂ (registry number = 87339–38–6).^[6] See HIDA scan.

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.

[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.

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