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Dimethyl maleate

Base Information
  • Chemical Name:Dimethyl maleate
  • CAS No.:624-48-6
  • Molecular Formula:C6H8O4
  • Molecular Weight:144.127
  • Hs Code.:2917.19
  • European Community (EC) Number:210-848-5
  • UNII:K39366X5N0
  • ChEMBL ID:CHEMBL2259700
  • DSSTox Substance ID:DTXSID4040765
  • Nikkaji Number:J45.018I
  • NSC Number:5161
  • Wikidata:Q2377169
  • Wikipedia:Dimethyl_maleate
  • Mol file:624-48-6.mol
Dimethyl maleate

Synonyms:dimethyl maleate;maleic acid, dimethyl ester

Suppliers and Price of Dimethyl maleate
Supply Marketing:
Business phase:
The product has achieved commercial mass production*data from LookChem market partment
Manufacturers and distributors:
  • Manufacture/Brand
  • Chemicals and raw materials
  • Packaging
  • price
  • TRC
  • Dimethyl maleate
  • 10g
  • $ 150.00
  • TCI Chemical
  • Dimethyl Maleate >97.0%(GC)
  • 500mL
  • $ 51.00
  • TCI Chemical
  • Dimethyl Maleate >97.0%(GC)
  • 25mL
  • $ 26.00
  • Sigma-Aldrich
  • Dimethyl maleate 96%
  • 1kg
  • $ 110.00
  • Sigma-Aldrich
  • Dimethyl maleate 96%
  • 100g
  • $ 25.40
  • Frontier Specialty Chemicals
  • Dimethyl maleate 96%
  • 100g
  • $ 29.00
  • Frontier Specialty Chemicals
  • Dimethyl maleate 96%
  • 500g
  • $ 37.00
  • Crysdot
  • Dimethyl maleate 95+%
  • 500g
  • $ 82.00
  • Biosynth Carbosynth
  • Dimethyl maleate
  • 250 g
  • $ 90.00
  • Biosynth Carbosynth
  • Dimethyl maleate
  • 2 Kg
  • $ 300.00
Total 128 raw suppliers
Chemical Property of Dimethyl maleate
Chemical Property:
  • Appearance/Colour:colourless liquid 
  • Vapor Pressure:0.475mmHg at 25°C 
  • Melting Point:-19 °C 
  • Refractive Index:1.442 - 1.443 
  • Boiling Point:193 °C at 760 mmHg 
  • Flash Point:91.1 °C 
  • PSA:52.60000 
  • Density:1.124 g/cm3 
  • LogP:-0.11140 
  • Storage Temp.:Store below +30°C. 
  • Solubility.:water: soluble77.9g/L at 20°C 
  • Water Solubility.:Miscible with water. 
  • XLogP3:0.7
  • Hydrogen Bond Donor Count:0
  • Hydrogen Bond Acceptor Count:4
  • Rotatable Bond Count:4
  • Exact Mass:144.04225873
  • Heavy Atom Count:10
  • Complexity:141
Purity/Quality:

99% *data from raw suppliers

Dimethyl maleate *data from reagent suppliers

Safty Information:
  • Pictogram(s): HarmfulXn 
  • Hazard Codes:Xn,C 
  • Statements: 21/22-36/37/38-43-37-34-22 
  • Safety Statements: 26-36/37-23-45-36/37/39 
MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:
  • Chemical Classes:Other Classes -> Esters, Other
  • Canonical SMILES:COC(=O)C=CC(=O)OC
  • Isomeric SMILES:COC(=O)/C=C\C(=O)OC
  • General Description Dimethyl maleate is a dienophile used in Diels-Alder reactions, as demonstrated in the synthesis of polycyclic β-carboline scaffolds and hydroxylated indolizidinones. It facilitates the formation of complex heterocyclic structures, such as in the in situ reaction with an unstable nitrone derived from C2 symmetric piperidine, leading to protected dihydroxyindolizidinone derivatives. Its role in these reactions highlights its utility in constructing biologically relevant molecular frameworks.
Technology Process of Dimethyl maleate

There total 127 articles about Dimethyl maleate 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:
Guidance literature:
With boron trifluoride; at 65 ℃; for 0.333333h;
DOI:10.1021/ac049919h
Guidance literature:
With hydrogen; montmorillonit-bipyridinpalladium(II)-acetate; In tetrahydrofuran; Ambient temperature;
Guidance literature:
With sulfuric acid; at 10 - 20 ℃; regioselective reaction;
DOI:10.1016/j.tetlet.2011.04.100
Refernces

Novel chemistry of β-carbolines. Expedient synthesis of polycyclic scaffolds

10.1016/j.tet.2009.02.051

The study focuses on the novel chemistry of β-carbolines, specifically exploring the synthesis of polycyclic scaffolds through various chemical reactions. β-carbolines are heterocyclic compounds found in numerous natural alkaloids with diverse biological activities, making them of interest for pharmaceutical applications. The researchers utilized ring-closing metathesis (RCM) and combined it with other cyclization processes such as Diels-Alder reactions to generate complex molecular structures in a single synthetic step. Chemicals used in the study include allyl-, vinyl-, ethynyl-, and propargyl-b-carbolines as substrates, as well as Grignard reagents and various catalysts like [Ru]-I, [Ru]-II, and [Ru]-III for metathesis reactions. Additionally, compounds like dimethyl acetylenedicarboxylate (DMAD) and dimethyl maleate were employed as dienophiles in Diels-Alder reactions. The purpose of these chemicals was to functionalize β-carbolines and construct more complex heterocycles, which could potentially lead to the development of new drugs with various therapeutic properties. The study also observed novel domino processes and rearrangements, such as Stevens rearrangement, providing insights into the complex polycyclic chemistry of β-carbolines.

A new nitrone from C2 symmetric piperidine for the synthesis of hydroxylated indolizidinone

10.1016/S0040-4039(02)02336-5

The research focuses on the synthesis of a new nitrone derived from C2 symmetric piperidine, which is used for the creation of hydroxylated indolizidinones. The purpose of this study was to develop an alternative synthetic pathway to these biologically active molecules, which are known as glycosidase inhibitors. The researchers achieved this by oxidizing a C2 symmetric piperidine, obtained through a ring enlargement process of the enantiopure protected (4R)-hydroxy-(2S)-hydroxymethyl pyrrolidine, using C-phenyl-N-phenylsulfonyloxaziridine. The resulting nitrone was too unstable for isolation and was therefore reacted in situ with dimethyl maleate, yielding a major adduct that was transformed into a protected dihydroxyindolizidinone. The conclusions of the research indicate that the synthetic process starting from a C2 symmetric piperidine can be considered an alternative method for synthesizing indolizidinones with a precise substitution pattern on the six-membered ring, despite the limited stability of the nitrone. Key chemicals used in this process include C-phenyl-N-phenylsulfonyloxaziridine, dimethyl maleate, and various reagents for the protection and oxidation steps.

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