Dimethyl itaconate

Base Information

• Chemical Name: Dimethyl itaconate
• CAS No.: 617-52-7
• Molecular Formula: C7H10O4
• Molecular Weight: 158.154
• Hs Code.: 29171900
• European Community (EC) Number: 210-519-6
• NSC Number: 9385
• UNII: 11JIB0YI93
• DSSTox Substance ID: DTXSID80210701
• Nikkaji Number: J45.119C
• Wikidata: Q63396620
• ChEMBL ID: CHEMBL4750162
• Mol file: 617-52-7.mol

Synonyms:dimethyl itaconate;dimethylitaconate

Chemical Property of Dimethyl itaconate

Chemical Property:

• Appearance/Colour: white crystalline low melting mass or liquid
• Vapor Pressure: 0.219mmHg at 25°C
• Melting Point: 37-41 °C(lit.)
• Refractive Index: 1.428
• Boiling Point: 207.999 °C at 760 mmHg
• Flash Point: 89.094 °C
• PSA: 52.60000
• Density: 1.084 g/cm³
• LogP: 0.27870
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Water Solubility.: slightly soluble
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 158.05790880
• Heavy Atom Count: 11
• Complexity: 183

Purity/Quality:

98%, ^*data from raw suppliers

Dimethyl itaconate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)CC(=C)C(=O)OC
• Uses: Dimethyl Itaconate is a chemical reagent used in the synthesis of functionalized 2-isoxazolines used in fragment-based drug discovery. Dimethyl itaconate may be used in functionalization of isotactic poly(propylene). It was used in crosslinking of polyesters: poly(isosorbide itaconate)and poly(isosorbide itaconate-co-succinate). Dimethyl itaconate can be used for the rhodium catalyzed asymmetric hydrogenation of (S)-dimethyl-2-methylsuccinate and (R)-methyl succinic acid dimethyl ester.

Technology Process of Dimethyl itaconate

There total 19 articles about Dimethyl itaconate 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: 93.07%

methanol (67-56-1) + 2-methylenesuccinic acid (97-65-4,25119-64-6) → Dimethyl itakonate (617-52-7)

Guidance literature:

With La³⁺SO₄^2-/TiO₂-SiO₂; at 120 ℃; for 7h; Reagent/catalyst; Time; Concentration; Autoclave;

DOI:10.1016/j.molcata.2012.11.008

Reference yield: 90.0%

methanol (67-56-1) + 2-methylenesuccinic acid (97-65-4,25119-64-6) → 4-methoxy-2-methylene-4-oxobutanoic acid (7338-27-4) + Dimethyl itakonate (617-52-7)

Guidance literature:

With thionyl chloride; at 25 - 27 ℃; for 19h;

Reference yield: 85.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) + methyl iodide (74-88-4) → Dimethyl itakonate (617-52-7)

Guidance literature:

2-methylenesuccinic acid; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; for 0.166667h;

methyl iodide; In acetonitrile; at 20 ℃; for 4h;

DOI:10.1080/00397910802238809

upstream raw materials:

2-methylenesuccinic acid

dimethyl sulfate

nitromethane

dimethylfumarate

Downstream raw materials:

dimethyl 2-(tosylmethyl)fumarate

methyl 1-(methoxycarbonyl)-4-methyl-3-cyclohexene-1-acetate

methyl 2-oxoquinoline-3-acetate

dimethyl 2-benzylsuccinate

Refernces

Synthesis, properties and applications of BICAP: A new family of carbazole-based diphosphine ligands

10.1002/adsc.200303241

The research focuses on the development and application of a new family of bidentate phosphine ligands based on the biscarbazole backbone, known as BICAP ligands. These ligands were synthesized and applied in ruthenium- and rhodium-catalyzed asymmetric hydrogenations of methyl acetoacetate and dimethyl itaconate, achieving enantiomeric excesses of 98% and 55%, respectively. The nitrogen atoms in the BICAP ligands allow for the introduction of various substituents, enabling the creation of structurally similar but electronically different ligands to fine-tune the catalytic reactions. Key chemicals involved in the synthesis include diol BICOL, dinonaflate, diphenylphosphine, and various electrophiles such as methyl iodide and trifluoromethanesulfonic anhydride. The study also utilized solvents like acetonitrile, toluene, and phenylsilane, along with reagents like triethylamine, lithium aluminum hydride, and palladium acetate. The research highlights the versatility of the BICAP ligands in optimizing asymmetric catalytic reactions through electronic modifications.