3647-74-3

Basic information

• Product Name: 5-NORBORNENE-2,3-DICARBOXIMIDE
• Synonyms: 4,7-METHANO-1H-ISOINDOLE-1,3(2H)-DIONE,3α,4,7,7α-TETRAHYDRO-;3(2H)-dione,3a,4,7,7a-tetrahydro-;4,7-Methano-1H-isoindole-1;5-Norbonene-2,3-dicarboximide;Nsc147237;Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxiMide;3a,4,7,7a-Tetrahydro-1H-4,7-Methanoisoindole-1,3(2H)-dione;4,7-METHANO-1H-ISOINDOLE-1, 3(2H)-DIONE,3A,4,7,7A-TETRAHYDRO-
• CAS NO: 3647-74-3
• Molecular Formula: C₉H₉NO₂
• Molecular Weight: 163.17326
• Product Categories: Norbornene Derivatives
• Mol File: 3647-74-3.mol

Chemical Properties

• Melting Point: 186.0 to 190.0 °C
• Boiling Point: 362.1°Cat760mmHg
• Flash Point: 177.1°C
• Appearance: /
• Density: 1.339g/cm³
• Vapor Pressure: 1.97E-05mmHg at 25°C
• Refractive Index: 1.585
• Storage Temp.: Inert atmosphere,Room Temperature
• CAS DataBase Reference: 5-NORBORNENE-2,3-DICARBOXIMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-NORBORNENE-2,3-DICARBOXIMIDE(3647-74-3)
• EPA Substance Registry System: 5-NORBORNENE-2,3-DICARBOXIMIDE(3647-74-3)

Safety Data

• Hazardous Substances Data: 3647-74-3(Hazardous Substances Data)

Usage

Uses

Used in Adhesives Production:
5-NORBORNENE-2,3-DICARBOXIMIDE is used as a crosslinking agent for improving the mechanical properties and thermal stability of adhesives, ensuring stronger bonds and better performance under varying temperature conditions.
Used in Coatings Industry:
In the coatings industry, 5-NORBORNENE-2,3-DICARBOXIMIDE is utilized as a crosslinking agent to enhance the durability and heat resistance of coatings, providing a longer-lasting and more robust protective layer for various surfaces.
Used in Resins Production:
5-NORBORNENE-2,3-DICARBOXIMIDE is employed as a crosslinking agent in the production of resins, contributing to the improvement of the resins' mechanical strength and thermal stability, which is crucial for applications requiring high-performance materials.
Used as a Curing Agent for Epoxy Resins:
5-NORBORNENE-2,3-DICARBOXIMIDE is used as a curing agent for epoxy resins, facilitating the hardening process and resulting in a more durable and heat-resistant final product.
Used as a Flame Retardant in Plastics:
In the plastics industry, 5-NORBORNENE-2,3-DICARBOXIMIDE is used as a flame retardant to improve the fire safety of plastic materials, reducing their flammability and providing additional protection in case of fire.
It is important to handle 5-NORBORNENE-2,3-DICARBOXIMIDE with care, as it may cause irritation to the skin, eyes, and respiratory system if not properly managed.

InChI:InChI=1/C9H9NO2/c11-8-6-4-1-2-5(3-4)7(6)9(12)10-8/h1-2,4-7H,3H2,(H,10,11,12)

Upstream product

• 826-62-0 5-norbornene-2,3-dicarboxylic anhydride 
• 74-89-5 methylamine 

Downstream Products

• 797801-56-0 4-aza-4-(3-phenyl(2H,4H-benzo[2,4-3]1,3-oxazaperhydroin-6yl))tri-cycle[5.2.1.0<2,6>]dec-8-ene-3,5-dione 

Relevant articles and documents

Synthesis of N-unsubstituted cyclic imides from anhydride with urea in deep eutectic solvent (DES) choline chloride/urea

N-Unsubstituted cyclic imides were readily synthesized in deep eutectic solvent (DES) choline chloride (ChCl)/urea from anhydrides with urea. Urea serves as both a DES component and a nitrogen source, which endows the protocol with advantages of smooth reaction, easy separation of products, simple recovery and recycling of ChCl/urea.

OLEFIN CYCLISATIONS OF HINDERED α-ACYLIMINIUM IONS

Stereocontrolled NaBH4/H+-reduction of 3,4-cis-disubstituted N-alkenyl imides 1-5 leads to secondary hydroxylactams.Tertiary hydroxylactams are formed via addition of MeMgCl to imides 2 and 4.HCOOH-Cyclisation of the hydroxylactams affords polycyclic piperidines through stereoselective α-acyliminium ring closure.Concomitant synchronous and stepwise cyclisation pathways are operative in the anti-periplanar addition of tertiary α-acyliminium ions to Me substituted olefins 8c and 11c.

Photochemistry of Aliphatic Imides. Synthesis of Azetidine-2,4-diones via Photochemical Isomerization of Succinimides and N-Formyl-N-methyl α, β -Unsaturated Amides

Photochemical reactions of alkyl-substituted succinimides and N-formyl-N-methyl α, β -unsaturated amides were studied.Photolysis of succinimide 1 gave azetidine-2,4-dione 2 together with a small amount of 3.The photoinduced ring-contraction reaction is explained in terms of a two-photon mechanism.Similarly, several other succinimide derivates photochemically gave the corresponding azetidine-2,4-diones.In addition, the photochemical cyclization of 3 to 2 was extended to the synthesis of azetidine-2,4-diones from N-formyl-N-methyl α, β -unsaturated amides.