328081-58-9

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione, 2-(3,5-difluorophenoxy)-
• CAS NO: 328081-58-9
• Molecular Formula: C14H7F2NO3
• Molecular Weight: 275.211
• Mol File: 328081-58-9.mol

Chemical Properties

• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione, 2-(3,5-difluorophenoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione, 2-(3,5-difluorophenoxy)-(328081-58-9)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione, 2-(3,5-difluorophenoxy)-(328081-58-9)

Safety Data

• Hazardous Substances Data: 328081-58-9(Hazardous Substances Data)

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 156545-07-2 3,5-difluorophenylboronic acid 

Downstream Products

• 1443440-60-5 N-(3,5-difluorophenoxy)acetamide 

Relevant articles and documents

The copper-mediated cross-coupling of phenylboronic acids and N-hydroxyphthalimide at room temperature: synthesis of aryloxyamines.

[figure: see text] A novel route to aryloxyamines via the copper-mediated cross-coupling of N-hydroxyphthalimide and phenylboronic acids is reported. The reaction is mediated by selected copper(I) and (II) salts in the presence of pyridine and is tolerant of several functional groups on the phenylboronic acid. The phthallmide group is removed using hydrazine to afford the corresponding aryloxyamine.

Rhodium(III)-catalyzed C-H olefination for the Synthesis of ortho-alkenyl phenols using an oxidizing directing group

By using an oxidizing directing group, a mild, efficient Rh(III) catalyzed C-H olefination reaction between N-phenoxyacetamides and alkenes was developed. This reaction provided a straightforward way for the synthesis of ortho-alkenyl phenols, and the directing group is traceless in the product.

Inhibitors of transthyretin amyloid fibril formation

Bisaryloxime ethers and bisarylhydroazones are shown to be effective for inhibiting formation of amyloid fibrils of transthyretin.

Bisaryloxime ethers as potent inhibitors of transthyretin amyloid fibril formation

Amyloid fibril formation by the plasma protein transthyretin (TTR), requiring rate-limiting tetramer dissociation and monomer misfolding, is implicated in several human diseases. Amyloidogenesis can be inhibited through native state stabilization, mediated by small molecule binding to TTR's primarily unoccupied thyroid hormone binding sites. New native state stabilizers have been discovered herein by the facile condensation of arylaldehydes with aryloxyamines affording a bisarylaldoxime ether library. Of the library's 95 compounds, 31 were active inhibitors of TTR amyloid formation in vitro. The bisaryloxime ethers selectively stabilize the native tetrameric state of TTR over the dissociative transition state under amyloidogenic conditions, leading to an increase in the dissociation activation barrier. Several bisaryloxime ethers bind selectively to TTR in human blood plasma over the plethora of other plasma proteins, a necessary attribute for efficacy in vivo. While bisarylaldoxime ethers are susceptible to degradation by N-O bond cleavage, this process is slowed by their binding to TTR. Furthermore, the degradation rate of many of the bisarylaldoxime ethers is slow relative to the half-life of plasma TTR. The bisaryloxime ether library provides valuable structure-activity relationship insight for the development of structurally analogous inhibitors with superior stability profiles, should that prove necessary.