| Customization: | Available |
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| CAS No.: | 541-59-3 |
| Formula: | C4h3no2 |
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Maleimide is an important nitrogen-containing heterocyclic organic compound with a chemical formula of C4H3NO2. The molecule contains a five-membered ring (composed of two carbon atoms, two carbonyl groups and an imino group). It has unique chemical activity and structural characteristics and is widely used in chemical, material and other fields. The following is a brief introduction from the aspects of structure, properties, preparation and application characteristics:
I. Basic structure and properties
Structural characteristics: The molecular skeleton is a five-membered ring, in which two adjacent carbon atoms are connected to the carbonyl group (C=O) and the other carbon atom is connected to the imino group (-NH-). The unsaturated structure of the ring makes it highly reactive, especially prone to addition reactions (such as Diels-Alder reaction) and sulfhydryl (-SH) specific reactions.
Physical properties: The pure product is white crystals with a melting point of about 92-94ºC. It is soluble in organic solvents such as acetone, ethanol, ether, and slightly soluble in water. It has a certain irritation and is irritating to the skin, mucous membranes and eyes. Protection should be taken during operation.
Chemical properties: Because it contains unsaturated double bonds and polar groups, it has high chemical activity and can undergo polymerization, cross-linking, nucleophilic addition reactions, etc. It can also be used as a monomer to copolymerize with other compounds to form derivatives with diverse properties.
2. Main preparation methods
Maleimide is usually prepared by the reaction of maleic anhydride and amine compounds. The core steps are:
Maleic anhydride reacts with ammonia (or primary amine) under certain conditions to generate maleamic acid;
Maleamic acid undergoes a dehydration ring closure reaction (usually at high temperature or under the action of a catalyst) to generate maleimide.
The process is mature, the raw materials are easy to obtain (maleic anhydride is a common chemical raw material), and the product purity can be controlled by adjusting the reaction conditions, which is suitable for industrial production.
3. Core application areas
Polymer materials: As a monomer or cross-linking agent, it is used to synthesize heat-resistant polymers and modified resins (such as epoxy resins and polyesters) to improve the high temperature resistance, mechanical strength and chemical resistance of the material. It is used in aerospace composite materials, printed circuit boards (PCBs), high temperature resistant rubbers, etc.
Biomedicine: It is used as a protein crosslinker for biomolecule research and antibody-drug conjugate (ADC) preparation by utilizing its specific reaction with thiol groups; at the same time, its derivatives can be used as drug intermediates for the synthesis of antibacterial, anti-tumor and other active molecules.
Organic synthesis: It participates in the Diels-Alder reaction as a dienophile and is used to construct complex organic molecular skeletons. It is an important intermediate for the synthesis of natural products and the preparation of fine chemicals.
IV. Derivatives and development.
| Melting point | 91-93 °C (lit.) |
| Boiling point | 97-103°C 5mm |
| density | 1,2493 g/cm3 |
| refractive index | 1.4543 (estimate) |
| Fp | 97-103°C/5mm |
| storage temp. | Inert atmosphere,Room Temperature |
| pka | 8.52±0.20(Predicted) |
| form | Fine Crystalline Powder |
| color | White to slightly yellow |
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