7685-94-1

Usage

Usage

Production of polymers and copolymers (e.g. polyvinylpyrrolidone), cross-linking agent in hydrogels, precursor to specialty chemicals

Physical properties

Colorless to pale yellow liquid, characteristic odor

Safety

Relatively safe, low toxicity when handled properly

Applications

Pharmaceutical, cosmetic, and food industries (as a binder, film-former, and viscosity enhancer)

InChI:InChI=1/C6H5NO2/c1-2-7-5(8)3-4-6(7)9/h2-4H,1H2

Upstream product

• 541-59-3 maleiimide 
• 108-05-4 vinyl acetate 

Downstream Products

• 1446103-01-0 dimethyl 2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)cyclopropane-1,1-dicarboxylate 

Relevant academic research and scientific papers

Divergent Reactivity of Thioalkynes in Lewis Acid Catalyzed Annulations with Donor–Acceptor Cyclopropanes

Efficient methods for the convergent synthesis of (poly)cyclic scaffolds are urgently needed in synthetic and medicinal chemistry. Herein, we describe new annulation reactions of thioalkynes with phthalimide-substituted donor–acceptor cyclopropanes, which gave access to highly substituted cyclopentenes and polycyclic ring systems. With silyl-thioalkynes, the Lewis acid catalyzed [3+2] annulation reaction with donor–acceptor cyclopropanes took place to afford 1-thio-cyclopenten-3-amines. On the other hand, an unprecedented polycyclic compound was formed with alkyl-thioalkynes through a reaction pathway directly involving the phthalimide group. The two transformations proceeded in good yields and tolerated a large variety of functional groups.

Catalytic Friedel-Crafts reaction of aminocyclopropanes

A Lewis acid catalyzed Friedel-Crafts reaction between donor-acceptor aminocyclopropanes and indoles and other electron-rich aromatic compounds is reported. Indole alkylation at the C3 position was generally obtained for a broad range of functional groups and substitution patterns. In the case of C3-substituted indoles, C2 alkylation was observed. The reaction gives a rapid access to gamma amino acid derivatives present in numerous bioactive molecules.

Synthesis of aminocyclobutanes by iron-catalyzed [2+2] cycloaddition

Fab Four: An iron-catalyzed [2+2] cycloaddition furnishes aminocyclobutanes with a broad range of substituents in excellent yields and diastereoselectivities. The products can be obtained on a gram scale and can be further converted to β-peptide derivatives in a few steps. Furthermore, a [4+2] cycloaddition between an aminocyclobutane and an olefin leads to the corresponding cyclohexylamines. Copyright