4408-64-4

Usage

Uses

Used in Chemical Synthesis:
N-Methyliminodiacetic acid is used as a reagent for the preparation of bis-(1H-benzoimidazol-2-ylmethyl)-methyl-amine by condensation with benzene-1,2-diamine. This application is crucial in the synthesis of various organic compounds and pharmaceuticals.
Used in Cross-Coupling Reactions:
In the field of organic chemistry, N-Methyliminodiacetic acid is utilized in Suzuki cross-coupling reactions with MIDA boronates. This process is essential for the formation of carbon-carbon bonds, which are vital in the synthesis of complex organic molecules and pharmaceuticals.
Used as a Protecting Group for Boronic Acids:
N-Methyliminodiacetic acid serves as a protecting group for boronic acids, which are important intermediates in organic synthesis. The protection of boronic acids with MIDA allows for selective reactions and prevents unwanted side reactions, thus improving the overall yield and purity of the target compounds.
Used as a Chelating Agent for Metals:
N-Methyliminodiacetic acid is used as a chelating agent for various metals. Its ability to form stable complexes with metal ions makes it a valuable tool in various industries, including the pharmaceutical, chemical, and environmental sectors. Chelating agents are essential for stabilizing metal ions, preventing metal-catalyzed reactions, and facilitating the separation and purification of metal-containing compounds.

InChI:InChI=1/C5H9NO4/c1-6(2-4(7)8)3-5(9)10/h2-3H2,1H3,(H,7,8)(H,9,10)/p-1

Upstream product

• 107-16-4 glycolonitrile 
• 74-89-5 methylamine 
• 79-11-8 chloroacetic acid 
• 50-00-0 formaldehyd 
• 142-73-4 iminodiacetic acid 
• 107-97-1 sarcosine 
• 109674-45-5 4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide 
• 1104637-53-7 B-ethynyl N-methyliminodiacetic acid boronate 
• 13968-48-4 ¹⁷O-water 
• 1104637-58-2 6-methyl-2-(pyridin-2-yl)-1,3,6,2-dioxazaborocane-4,8-dione 
• 1380504-41-5 1-(MIDA boryl)-1-phenylbut-3-en-1-yl isocyanate 
• 1380504-40-4 α-allyl-α-MIDA boryl phenyl acetic acid 
• 1380504-39-1 α-allyl-α-MIDA boryl phenyl acetaldehyde 
• 1380504-17-5 1-(MIDA boryl)-3-phenylpropyl isocyanate 

Downstream Products

• 5412-66-8 diethyl 2,2'-(methylimino)diacetate 
• 60725-35-1 1-methylpiperazine-3,5-dione 
• 13480-36-9 (N-methylimino)diacetic acid anhydride 
• 122485-04-5 4-methyl-1-<2-(1-pyrryl)phenylmethyl>piperazine-2,6-dione 
• 855229-93-5 bis-(2-hydroxy-2,2-diphenyl-ethyl)-methyl-amine 
• 124119-47-7 bis-(2-hydroxy-2,2-diphenyl-ethyl)-dimethyl-ammonium; iodide 
• 483989-18-0 N,N-bis[N-[2-(3,4,5-trimethoxyphenyl)-5-pyridyl]carbamoylmethyl]methylamine 
• 103823-15-0 K⁽¹⁺⁾*[Ru(CH₃N(CH₂COO)2)2]^(1-)*H₂O=K[Ru(CH₃N(CH₂COO)2)2]*H₂O 
• 75269-04-4 (C₆H₁₁)2Sn(CH₃N(CH₂CO₂)2) 
• 71160-37-7 sodium methyliminodiacetate 
• 1308400-81-8 2,6-difluoro-3-(6-methyl-4,8-dioxo-1,3,6,2-dioxazaborocan-2-yl)benzonitrile 
• 5995-25-5 N-methyliminobis(methylphosphonic acid) 
• 1257739-11-9 2-(4-methoxyphenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione 
• 109737-57-7 6-methyl-2-phenyl-1,3,6,2-dioxazaborocane-4,8-dione 

Relevant academic research and scientific papers

Multicomponent mapping of boron chemotypes furnishes selective enzyme inhibitors

Heteroatom-rich organoboron compounds have attracted attention as modulators of enzyme function. Driven by the unmet need to develop chemoselective access to boron chemotypes, we report herein the synthesis of α-and β-aminocyano(MIDA)boronates from borylated carbonyl compounds. Activity-based protein profiling of the resulting β-aminoboronic acids furnishes selective and cell-active inhibitors of the (ox)lipid-metabolizing enzyme α/β-hydrolase domain 3 (ABHD3). The most potent compound displays nanomolar in vitro and in situ IC50 values and fully inhibits ABHD3 activity in human cells with no detectable cross-reactivity against other serine hydrolases. These findings demonstrate that synthetic methods that enhance the heteroatom diversity of boron-containing molecules within a limited set of scaffolds accelerate the discovery of chemical probes of human enzymes.

Building Block Approach for the Synthesis of Sulfoximines

A cross-coupling strategy for the preparation of novel sulfoximines via preformed sulfoximidoyl-containing building blocks has been developed. It allows obtaining a wide range of products in good yields under mild reaction conditions, and it can be applied in late-stage functionalizations, as demonstrated by the synthesis of a sulfoximine-based analogue of a recently reported potent valosine-containing protein inhibitor.

A Mild Method for Making MIDA Boronates

We disclose that a predried form of methyliminodiacetic acid (MIDA), MIDA anhydride, acts as both a source of the MIDA ligand and an in situ desiccant to enable a mild and simple MIDA boronate synthesis procedure. This method expands the range of sensitive boronic acids that can be converted into their MIDA boronate counterparts. Further utilizing unique properties of MIDA boronates, we have developed a MIDA Boronate Maker Kit which enables the direct preparation and purification of MIDA boronates from boronic acids using only heating and centrifuge equipment that is widely available in laboratories that do not specialize in organic synthesis.

NOVEL BORONIC ESTERS AND METHODS FOR MAKING THE SAME

There is provide herein a compound of Formula (1): wherein R1, R2, R3, R4, and R5 are each independently H or an organic group.

Fe-Catalyzed Reductive Couplings of Terminal (Hetero)Aryl Alkenes and Alkyl Halides under Aqueous Micellar Conditions

The combination of a vinyl-substituted aromatic or heteroaromatic and an alkyl bromide or iodide leads, in the presence of Zn and a catalytic amount of an Fe(II) salt, to a net reductive coupling. The new C-C bond is regiospecifically formed at rt at the β-site of the alkene. The coupling only occurs in an aqueous micellar medium, where a radical process is likely, supported by several control experiments. A mechanism based on these data is proposed.

N-Arylated Sulfoximines as Cross-Coupling Building Blocks

The application of borylated N-aryl sulfoximines as newly designed synthetic building blocks in Suzuki-type cross coupling reactions offers rapid access to a wide range of N-biaryl derivatives with potential relevance for medicinal chemistry and crop protection in good to excellent yields (up to 98%). (Figure presented.).

A General Protocol for the Polycondensation of Thienyl N-Methyliminodiacetic Acid Boronate Esters to Form High Molecular Weight Copolymers

Thienyl di-N-methyliminodiacetic acid (MIDA) boronate esters are readily synthesized by electrophilic C-H borylation producing bench stable crystalline solids in good yield and excellent purity. Optimal conditions for the slow release of the boronic acid using KOH as the base in biphasic THF/water mixtures enables the thienyl MIDA boronate esters to be extremely effective homo-bifunctionalized (AA-type) monomers in Suzuki-Miyaura copolymerizations with dibromo-heteroarenes (BB-type monomers). A single polymerization protocol is applicable for the formation of five alternating thienyl copolymers that are (or are close analogues of) state of the art materials used in organic electronics. The five polymers were produced in excellent yields and with high molecular weights comparable to those produced using Stille copolymerization protocols. Therefore, thienyl di-MIDA boronate esters represent bench stable and low toxicity alternatives to highly toxic di-trimethylstannyl AA-type monomers that are currently ubiquitous in the synthesis of these important alternating copolymers.

A general method for interconversion of boronic acid protecting groups: Trifluoroborates as common intermediates

We have developed a general protocol for the interconversion of diverse protected boronic acids, via intermediate organotrifluoroborates. N-Methyliminodiacetyl boronates, which have been hitherto resistant to direct conversion to trifluoroborates, have been shown to undergo fluorolysis at elevated temperatures. Subsequent solvolysis of organotrifluoroborates in the presence of trimethylsilyl chloride and a wide range of bis-nucleophiles enables the generation of a variety of protected boronic acids.

Boroalkyl group migration provides a versatile entry into α-aminoboronic acid derivatives

A reaction exemplifying migration of boron-substituted carbon is described. We show that α-boroalkyl groups of transient boroalkyl acyl azide intermediates readily migrate from carbon to nitrogen. This process allows access to a new class of stable molecules, α-boryl isocyanates, from α-borylcarboxylic acid precursors. The methodology facilitates synthesis of a wide range of α-aminoboronic acid derivatives, including α,α-disubstituted analogues.

General method for synthesis of 2-heterocyclic N-methyliminodiacetic acid boronates

A wide range of 2-pyridyl and other difficult-to-access heterocyclic N-methyliminodiacetic acid boronates can be readily prepared from the corresponding bromides via a new method involving direct transligation of 2-heterocyclic trialkoxyborate salts with N-methyliminodiacetic acid (MIDA) at elevated temperatures.