N-Methyliminodiacetic acid

Base Information

• Chemical Name: N-Methyliminodiacetic acid
• CAS No.: 4408-64-4
• Molecular Formula: C5H9NO4
• Molecular Weight: 147.131
• Hs Code.: 29171900
• European Community (EC) Number: 224-557-6
• NSC Number: 11773
• UNII: SH1YP5H4NA
• DSSTox Substance ID: DTXSID00196033
• Nikkaji Number: J135.883I
• ChEMBL ID: CHEMBL1741474
• Mol file: 4408-64-4.mol

Synonyms:2-methyliminodiacetic acid;strombine

Chemical Property of N-Methyliminodiacetic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 2.75E-05mmHg at 25°C
• Melting Point: 220 °C (dec.)(lit.)
• Refractive Index: 1.4210 (estimate)
• Boiling Point: 332.772 °C at 760 mmHg
• PKA: pK1:2.15;pK2:10.09 (25°C)
• Flash Point: 155.055 °C
• PSA: 77.84000
• Density: 1.367 g/cm³
• LogP: -0.91260
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Methanol (Slightly, Heated, Sonicated), Water (Soluble)
• Water Solubility.: Soluble in water. Slightly soluble in dimethyl sulfoxide.
• XLogP3: -3.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 147.05315777
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

99% ^*data from raw suppliers

N-Methyliminodiacetic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CN(CC(=O)O)CC(=O)O
• Uses: N-Methyliminodiacetic acid is used to prepare bis-(1H-benzoimidazol-2-ylmethyl)-methyl-amine by condensation with benzene-1,2-diamine. It is involved in Suzuki cross-coupling with N-methyliminodiacetic acid (MIDA) boronates. It acts as a reagent utilized for protecting boronic acids and as a chelating agent for various metals.

Technology Process of N-Methyliminodiacetic acid

There total 19 articles about N-Methyliminodiacetic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 93.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + iminodiacetic acid (142-73-4) → N-methyliminodiacetic acid (4408-64-4)

Guidance literature:

iminodiacetic acid; With formic acid; at 90 ℃; for 0.5h;

formaldehyd; In water; for 1h; Reflux;

DOI:10.1021/jacs.9b04510

Reference yield: 49.0%

sarcosine (107-97-1,25951-24-0) + chloroacetic acid (79-11-8) → N-methyliminodiacetic acid (4408-64-4)

Guidance literature:

With lithium hydroxide;

DOI:10.1246/bcsj.57.1097

Reference yield: 38.0%

4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide (109674-45-5) → N-methyliminodiacetic acid (4408-64-4)

Guidance literature:

In methanol; water; refluxing (2 h); solvent removal (vac.), crystn. (acetone);

DOI:10.1016/0277-5387(96)00109-X

upstream raw materials:

glycolonitrile

methylamine

chloroacetic acid

formaldehyd

Downstream raw materials:

ammonia

methylammonium carbonate

methylamine

N,N-bis[N-[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]carbamoylmethyl]methylamine

Refernces

• 1、 Steinkamp, Anne-Dorothee,Wiezorek, Stefan,Brosge, Felix,Bolm, Carsten. "Building Block Approach for the Synthesis of Sulfoximines". . p. 5348 - 5351. Retrieved 2016.
• 2、 -. "NOVEL BORONIC ESTERS AND METHODS FOR MAKING THE SAME". . . Retrieved 2020/12/20.
• 3、 Bachon, Anne-Katrin,Steinkamp, Anne-Dorothee,Bolm, Carsten. "N-Arylated Sulfoximines as Cross-Coupling Building Blocks". supporting information. p. 1088 - 1093. Retrieved 2018/01/27.