13658-97-4

Usage

Common use

Cross-linking agent in high-performance polymers

Applications

Engineering plastics, adhesives, coatings, and composites

Physical state

Colorless to pale yellow liquid

Odor

Faint amine odor

Hazard classification

Classified as a hazardous substance

Potential health effects

Causes skin and eye irritation, harmful if swallowed or inhaled

Workplace hazard

Considered a workplace hazard

Safety precautions

Handle with caution in a well-ventilated area and with appropriate personal protective equipment

Upstream product

• 124-09-4 1,6-Hexanediamine 
• 591-50-4 iodobenzene 
• 13658-99-6 2-(6-(phenylamino)hexyl)isoindoline-1,3-dione 

Downstream Products

• 1155-66-4 N,N'-diphenyl-hexanediyldiamine 

Relevant academic research and scientific papers

A Nanocrystal Catalyst Incorporating a Surface Bound Transition Metal to Induce Photocatalytic Sequential Electron Transfer Events

Heterogeneous photocatalysis is less common but can provide unique avenues for inducing novel chemical transformations and can also be utilized for energy transductions, i.e., the energy in the photons can be captured in chemical bonds. Here, we developed a novel heterogeneous photocatalytic system that employs a lead-halide perovskite nanocrystal (NC) to capture photons and direct photogenerated holes to a surface bound transition metal Cu-site, resulting in a N-N heterocyclization reaction. The reaction starts from surface coordinated diamine substrates and requires two subsequent photo-oxidation events per reaction cycle. We establish a photocatalytic pathway that incorporates sequential inner sphere electron transfer events, photons absorbed by the NC generate holes that are sequentially funneled to the Cu-surface site to perform the reaction. The photocatalyst is readily prepared via a controlled cation-exchange reaction and provides new opportunities in photodriven heterogeneous catalysis.

Synthesis and Characterization of Nitric Oxide-Releasing Platinum(IV) Prodrug and Polymeric Micelle Triggered by Light

Herein, we report the proof of concept of photoresponsive chemotherapeutics comprising nitric oxide-releasing platinum prodrugs and polymeric micelles. Photoactivatable nitric oxide-releasing donors were integrated into the axial positions of a platinum(IV) prodrug, and the photolabile hydrophobic groups were grafted in the block copolymers. The hydrophobic interaction between nitric oxide donors and the photolabile groups allowed for the loading of platinum drugs and nitric oxide-releasing donors in the photolabile polymeric micelles. After cellular uptake of micelles, light irradiation induced the release of nitric oxide, which sensitized the cancer cells. Simultaneously, photolabile hydrophobic groups were cleaved from micelles, and the nitric oxide-releasing donor was altered to be more hydrophilic, resulting in the rapid release of platinum(IV) prodrugs. The strategy of using platinum(IV) prodrugs and nitric oxide led to enhanced anticancer effects.

Cleavage of the etheric bond in cyclopentadienyliron phenolphthalein complexes

The reaction of aliphatic primary amines with phenolphthalein-containing dicyclopentadienyliron complexes led to etheric bond cleavage. This unique cleavage reaction is due to nucleophilic attack by the amines ipso to the etheric group of the complexed arene, which is activated by coordination to the cationic cyclopentadienyliron moiety.

PROCESS FOR PREPARING SYNTHETIC MATRIX METALLOPROTEASE INHIBITORS

Synthetic mammalian matrix metalloprotease inhibitors are disclosed that are useful for treating or preventing diseases wherein said diseases are caused by unwanted mammalian matrix metalloprotease activity and include skin disorders, keratoconus, restenosis, rheumatoid arthritis, wounds, cancer, angiogenesis and shock.

MATRIX METALLOPROTEASE INHIBITORS

Compounds of the formulas STR1 wherein each R 1 is independently H or alkyl (1-8C) and R 2 is alkyl (1-8C) or wherein the proximal R 1 and R 2 taken together are--(CH 2) p--wherein p=3-5;R 3 is H or alkyl (1-4C);R 4 is fused or conjugated unsubstituted or substituted bicycloaryl methylene;n is 0, 1 or 2; m is 0 or 1; andX is OR 5 or NHR 5, wherein R. sup.5 is H or substituted or unsubstituted alkyl (1-12C), aryl (6-12C), aryl alkyl (6-16C); orX is an amino acid residue or amide thereof; orX is the residue of a cyclic amine or heterocyclic amine;wherein R 6 is H or lower alkyl (1-4C) and R 7 is H, lower alkyl (1-4C) or an acyl group, and wherein--CONR 3--is optionally in modified isosteric form are useful for treating conditions which are characterized by unwanted matrix metalloprotease activities.

MATRIX METALLOPROTEASE INHIBITORS

Compounds of the formulas STR1 wherein each R 1 is independently H or alkyl (1-8C) and R 2 is alkyl (1-8C) or wherein the proximal R 1 and R 2 taken together are--(CH 2) p--wherein p=3-5;R 3 is H or alkyl (1-4C);R. sup.4 is fused or conjugated unsubstituted or substituted bicycloaryl methylene;n is 0, 1 or 2; m is 0 or 1; andx is OR 5 or NHR 5, wherein R. sup.5 is H or substituted or unsubstituted alkyl (1-12C), aryl (6-12C), aryl alkyl (6-16C); orX is an amino acid residue or amide thereof; orX is the residue of a cyclic amine or heterocyclic amine;Y is selected from the group consisting of R 7 ONR 6 CONR 6-, R 6 2 NCONOR 7-, and R 6 CONOR. sup.7-, wherein each R 6 is independently H or lower alkyl (1-4C); R 7 is lower alkyl (1-4C) or an acyl group; andwherein--CONR. sup.3--is optionally in modified isoteric form are inhibitors of matrix metalloproteases.

INHIBITION OF ANGIOGENESIS BY SYNTHETIC MATRIX METALLOPROTEASE INHIBITORS

Synthetic mammalian matrix metalloprotease inhibitors are useful in controlling angiogenesis. These compounds are thus useful in controlling the growth of tumors and in controlling neovascular glaucomas.

Treatment for tissue ulceration

Compounds of the formulas STR1 wherein R1 is H and R2 is alkyl (3-8C) or wherein R1 and R2 taken together are --(CH2)n -- wherein n=3-5; R3 is H or alkyl (1-4C); R4 is a substituted or unsubstituted fused or conjugated bicycloaryl methylene; X is OR5 or NHR5, wherein R5 is H or substituted or unsubstituted alkyl (1-12C), aryl (6-12C), aryl alkyl (6-16C); or X is an amino acid residue or amide thereof; or X is the residue of a cyclic amine or heterocyclic amine are useful for treating or preventing ulceration of tissue, especially cornea.