Itaconic anhydride

Base Information

• Chemical Name: Itaconic anhydride
• CAS No.: 2170-03-8
• Deprecated CAS: 141257-20-7,2055573-69-6
• Molecular Formula: C5H4O3
• Molecular Weight: 112.085
• Hs Code.: 2917 19 80
• European Community (EC) Number: 218-518-2
• NSC Number: 43979,43972
• UNII: Y455KS1U7Q
• DSSTox Substance ID: DTXSID8062230
• Nikkaji Number: J38.162D
• Wikipedia: Itaconic_anhydride
• Wikidata: Q15726050
• Metabolomics Workbench ID: 143528
• ChEMBL ID: CHEMBL87967
• Mol file: 2170-03-8.mol

Synonyms:Itaconicanhydride (6CI);Succinic anhydride, methylene- (8CI);Dihydro-3-methylene-2,5-furandione;Itaconicacid anhydride;Methylenesuccinic anhydride;NSC 43979;

Chemical Property of Itaconic anhydride

Chemical Property:

• Appearance/Colour: White to cream crystalline powder
• Melting Point: 66-68 °C(lit.)
• Refractive Index: 1.517
• Boiling Point: 239.4 °C at 760 mmHg
• Flash Point: 114.8 °C
• PSA: 43.37000
• Density: 1.26 g/cm³
• LogP: 0.01610
• Storage Temp.: Store below +30°C.
• Sensitive.: Moisture Sensitive
• Water Solubility.: Hydrolyzes in water.
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 112.016043985
• Heavy Atom Count: 8
• Complexity: 169

Purity/Quality:

99% ^*data from raw suppliers

Itaconic Anhydride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi; Xn
• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Plastics & Rubber -> Acid Anhydrides, Cyclic
• Canonical SMILES: C=C1CC(=O)OC1=O
• Uses: Itaconic anhydride is used in immobilization of β-glucosidase. It undergoes estrification to obtain suitable monomers for emulsion polymerization itaconates.

Technology Process of Itaconic anhydride

There total 16 articles about Itaconic anhydride 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: 100.0%

2-methylenesuccinic acid (97-65-4,25119-64-6) → itaconic acid anhydride (2170-03-8)

Guidance literature:

With trimethylsilylethoxyacetylene; In dichloromethane; at 40 ℃; for 5h;

DOI:10.1021/jo00372a010

Reference yield:

citric acid (77-92-9,906507-37-7) → diethyl 3-hydroxypentanedioate (638-18-6) + Mesaconic acid (498-24-8,7407-59-2) + 1 propene 1,2,3 tricarboxylic acid (499-12-7) + 2-methylenesuccinic acid (97-65-4,25119-64-6) + citraconic acid anhydride (616-02-4) + itaconic acid anhydride (2170-03-8)

Guidance literature:

With Sn/Pb solder; at 150 - 210 ℃;

DOI:10.1366/0003702953963229

Reference yield:

2-methylenesuccinic acid (97-65-4,25119-64-6) → citraconic acid anhydride (616-02-4) + itaconic acid anhydride (2170-03-8)

Guidance literature:

With acetic anhydride; at 80 ℃;

upstream raw materials:

cis-aconitic anhydride

2,6-dioxo-3,6-dihydro-2H-pyran-4-carboxylic acid

1 propene 1,2,3 tricarboxylic acid

2-methylenesuccinic acid

Downstream raw materials:

2-methylene-succinic acid 4-ethyl ester

1-(4-hydroxy-phenyl)-3-methylene-pyrrolidine-2,5-dione

1-(2-methoxy-phenyl)-3-methylene-pyrrolidine-2,5-dione

2-(carboxymethyl)bicyclo[2.2.1]hept-5-ene-2-carboxylic acid

Refernces

Assembly of four diverse heterocyclic libraries enabled by prins cyclization, Au-catalyzed enyne cycloisomerization, and automated amide synthesis

10.1021/jo301061r

The research describes a unified synthetic strategy for the efficient assembly of four diverse heterocyclic libraries, which are important for applications in organic synthesis, chemical biology, and pharmaceutical research. The synthesis began with the creation of a range of structurally diverse pyrrolidinones or piperidinones using readily available amines, ketoesters, and unsaturated anhydrides. The use of tetrahydropyran-containing ketoesters enabled the fusion of pyran and piperidinone cores. The researchers also developed an Au(I)-catalyzed cycloisomerization of alkyne-containing enamides to expand heterocyclic diversity, providing access to a wide range of bicyclic and tricyclic dienamides. The final stage involved diversifying the initially produced carboxylic acids using a fully automated platform for amide synthesis, delivering 1872 compounds with high diastereomeric and chemical purity without chromatographic purification. Key chemicals used in this research include various amines, ketoesters, maleic and itaconic anhydrides, and Au(I) catalysts. The innovative aspects of this work include the development of the automated amide synthesis protocol and the use of Au(I)-catalyzed cycloisomerization to achieve structural diversity in the heterocyclic libraries.

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