493040-01-0

Basic information

• Product Name: N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide
• Synonyms: N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide
• CAS NO: 493040-01-0
• Molecular Weight: 285.256
• Mol File: 493040-01-0.mol

Chemical Properties

• CAS DataBase Reference: N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide(493040-01-0)
• EPA Substance Registry System: N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide(493040-01-0)

Safety Data

• Hazardous Substances Data: 493040-01-0(Hazardous Substances Data)

Upstream product

• 6118-51-0 exo-3,6-epoxy-1,2,3,6-tetrahydrophthalic anhydride 
• 118-92-3 anthranilic acid 

Relevant articles and documents

Maleimidophenyl isocyanates as postpolymerization modification agents and their applications in the synthesis of block copolymers

The maleimide structure is highly reactive, exemplified by thiol–ene click reactions with thiols and Diels–Alder reactions with furans. Although postpolymerization modifications and macromolecular conjugations involving maleimide units have been widely studied, mostly due to their selectivity and high reactivity, little has been reported on the one-pot postpolymerization introduction of maleimides in polymer chains. Herein, we report p-maleimidophenyl isocyanate and its derivatives as modification agents to introduce maleimide moieties by reaction with hydroxy groups into polymer chains. The high reactivity of the resulting modification agents and of the corresponding maleimide structures once inserted in the polymer chains was examined by studying their reaction kinetics. Furthermore, these modification agents were successfully applied to the synthesis of macromonomers for graft polymerization and various block copolymers, with, for example, AB-type, star-shaped, and H-shaped architectures.

Synthesis and structural characterization of n-(2-carboxyphenyl)-exo-7-oxa- bicyclo[2,2,1]hept-5-ene-2,3-dicarboximide

The compound N-(2-carboxyphenyl)-exo-7-oxa-bicyclo[2,2,1]hept-5-ene-2,3- dicarboximide (C15H11NO5, Mr = 285.25) was synthesized and characterized by elemental analysis, 1H NMR spectra, IR spectra and single crystal X-ray diffraction. The crystal belongs to monoclinic, space group P21/n, with a = 8.4994(8), b = 14.6499(15), c = 10.2880(10) ?, b = 101.5890(10), V = 1254.9(2) ?3, Z = 4, Dc = 1.510 g/ cm3, l = 0.71073 ?, (MoKa) = 0.115 mm-1, F(000) = 592. The final refinement gave R = 0.0374, wR(F2) = 0.0856 for 2,201 observed reflections with I > 2s(I). The structure of the compound comprises a racemic mixture of chiral molecules containing four stereogenic centres. X-Ray diffraction analysis reveals that the cyclohexane ring tends towards a boat conformation, the tetrahydrofuran ring and the dihydrofuran ring adopt envelope conformations. The dihedral angle between the pyrrolidine-2,5-dione plane and the aromatic ring is 65.0 (1). The crystal structure is stabilized by O-HO and C-HO hydrogen bonds.