13480-36-9

Basic information

• Product Name: MIDA anhydride
• Synonyms: 4-Methylmorpholine-2,6-dione;MIDA anhydride;4-Methylmorpholine-2,6-dione 97%;4-methyl-2,6-Morpholinedione;(N-methylimino)diacetic acid anhydride
• CAS NO: 13480-36-9
• Molecular Formula: C₅H₇NO₃
• Molecular Weight: 129.11398
• Mol File: 13480-36-9.mol

Chemical Properties

• Melting Point: 41-45°C
• Boiling Point: 252.5±33.0 °C(Predicted)
• Flash Point: >110℃
• Appearance: /
• Density: 1.271±0.06 g/cm3(Predicted)
• PKA: 3.35±0.20(Predicted)
• CAS DataBase Reference: MIDA anhydride(CAS DataBase Reference)
• NIST Chemistry Reference: MIDA anhydride(13480-36-9)
• EPA Substance Registry System: MIDA anhydride(13480-36-9)

Safety Data

• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39
• WGK Germany: 1
• Hazardous Substances Data: 13480-36-9(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
MIDA anhydride is used as a key intermediate for the synthesis of pharmaceuticals, contributing to the development of new drugs and therapeutic agents. Its ability to form MIDA boronates allows for the creation of complex molecular structures that can target specific biological pathways and diseases.
Used in Agrochemical Industry:
In the agrochemical sector, MIDA anhydride is utilized as a precursor for the synthesis of agrochemicals, such as pesticides and herbicides. Its role in creating MIDA boronates enables the development of more effective and targeted agricultural chemicals that can improve crop protection and yield.
Used in Materials Science:
MIDA anhydride is employed as a building block in the synthesis of advanced materials, including those used in nanotechnology, polymers, and other high-performance materials. Its versatility in organic synthesis allows for the creation of novel materials with unique properties and applications.
Used in Coordination Chemistry:
MIDA anhydride is used as a ligand in coordination chemistry, where it can form stable complexes with various metal ions. These complexes have potential applications in catalysis, sensing, and other areas of chemistry and materials science.
Used in Metal-Catalyzed Coupling Reactions:
In the field of metal-catalyzed coupling reactions, MIDA anhydride serves as a coupling partner or a ligand, facilitating the formation of new chemical bonds and the synthesis of complex organic molecules. Its use in these reactions contributes to the advancement of organic synthesis methods and the development of new chemical compounds.

Upstream product

• 4408-64-4 N-methyliminodiacetic acid 
• 108-24-7 acetic anhydride 

Downstream Products

• 125686-89-7 (HOOCCH2)Sar-Aib 
• 1104637-03-7 C₁₀H₁₀BNO₆ 
• 1565829-30-2 phenethyl MIDA boronate 
• 1072960-66-7 4-formylphenylboronic acid 
• 1104637-53-7 B-ethynyl N-methyliminodiacetic acid boronate 

Relevant articles and documents

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.

CROSSLINKERS FOR MASS SPECTROMETRIC IDENTIFICATION AND QUANTITATION OF PEPTIDES

Crosslinking molecules that permit efficient identification of specifically associated proteins and the sites of crosslinking in biological or other samples include two cleavable bonds that are cleavable under the same conditions as peptide bonds in mass spectrometric determinations. Sets of the invention crosslinkers may be provided with isobaric labels containing reporter ions of differing molecular weights to permit relative quantitation of crosslinked protein pairs.

Identification of novel quinazolinedione derivatives as RORγt inverse agonist

Novel small molecules were synthesized and evaluated as retinoic acid receptor-related orphan receptor-gamma t (RORγt) inverse agonists for the treatment of inflammatory and autoimmune diseases. A hit compound, 1, was discovered by high-throughput screeni

Structure-activity relationships of imidazole-derived 2-[ N-carbamoylmethyl-alkylamino]acetic acids, dual binders of human insulin-degrading enzyme

Insulin degrading enzyme (IDE) is a zinc metalloprotease that degrades small amyloid peptides such as amyloid-a and insulin. So far the dearth of IDE-specific pharmacological inhibitors impacts the understanding of its role in the physiopathology of Alzheimer's disease, amyloid-a clearance, and its validation as a potential therapeutic target. Hit 1 was previously discovered by high-throughput screening. Here we describe the structure-activity study, that required the synthesis of 48 analogues. We found that while the carboxylic acid, the imidazole and the tertiary amine were critical for activity, the methyl ester was successfully optimized to an amide or a 1,2,4-oxadiazole. Along with improving their activity, compounds were optimized for solubility, lipophilicity and stability in plasma and microsomes. The docking or co-crystallization of some compounds at the exosite or the catalytic site of IDE provided the structural basis for IDE inhibition. The pharmacokinetic properties of best compounds 44 and 46 were measured in vivo. As a result, 44 (BDM43079) and its methyl ester precursor 48 (BDM43124) are useful chemical probes for the exploration of IDE's role.

CONDENSED HETEROCYCLIC COMPOUND

The present invention provides a fused heterocyclic compound having an RORγt inhibitory action. The present invention relates to a compound represented by the formula (I'): wherein each symbol is as defined in the specification, provided that 2-(2-((4-cyanophenyl)amino)-2-oxoethoxy)-N-(9-ethyl-9H-carbazol-3-yl)acetamide and N-(4-cyanophenyl)-N'-(9-ethyl-9H-carbazol-3-yl)-3-methylpentanediamide are excluded, or a salt thereof.

Methods for Forming Protected Organoboronic Acids

Described are methods of forming protected boronic acids that provide in a manner that is straightforward, scalable, and cost-effective a wide variety of building blocks, such as building blocks containing complex and/or pharmaceutically important structures, and/or provide simple or complex protected organoboronic acid building blocks. A first method includes reacting an imino-di-carboxylic acid and an organoboronate salt. A second method includes reacting a N-substituted morpholine dione and an organoboronic acid.

Structure-activity relationships of new N-acylanthranilic acid derivatives as plasminogen activator inhibitor-1 inhibitors

Novel anthranilic acid derivatives having substituted N-acyl side chains were designed and synthesized for evaluation as plasminogen activator inhibitor-1 (PAI-1) inhibitors. Compounds with a 4-diphenylmethyl-1-piperazinyl moiety on the acyl side chains in general exhibited potent in vitro PAI-1 inhibitory activity and good pharmacokinetic profiles after oral administration in rats. Compound 16f (TM5275) was identified as a promising candidate for further pharmacological evaluation.

MexAB-OprM specific efflux pump inhibitors in Pseudomonas aeruginosa. Part 5: Carbon-substituted analogues at the C-2 position

A series of 4-oxo-4H-pyrido[1,2-a]pyrimidine derivatives, derivatized at the 2-position with carbon-linked substituents, were synthesized and evaluated for their ability to potentiate the activity of the fluoroquinolone levofloxacin (LVFX) and the anti-pseudomonas β-lactam aztreonam (AZT) in Pseudomonas aeruginosa. Palladium-catalyzed cross-coupling methods were applied for the incorporation of aliphatic and aromatic substituents.

PHTHALAZINONE DERIVATIVES

A compound of formula (I); or an isomer, salt, solvate, chemically protected form, or prodrug thereof, wherein A and B together represent an optionally substituted, fused aromatic ring; RL is a C5-7aryl group substituted in the meta position by the group R2, and optionally further substituted; wherein R2 is selected from formula (II) and formula (III); and its use as a pharmaceutical, in particular for the treatment of diseases ameliorated by inhibiting the activity of PARP