Isobenzofuran

Base Information

• Chemical Name: Isobenzofuran
• CAS No.: 270-75-7
• Molecular Formula: C8H6O
• Molecular Weight: 118.135
• UNII: 9T5PJS6W2B
• DSSTox Substance ID: DTXSID00943009
• Metabolomics Workbench ID: 55091
• Nikkaji Number: J247.740H
• Wikidata: Q761117
• Wikipedia: Isobenzofuran
• Mol file: 270-75-7.mol

Synonyms:Isobenzofuran;2-benzofuran;2-Oxa-2H-isoindene;Benzo(C)furan;270-75-7;Benzo[c]furan;9T5PJS6W2B;UNII-9T5PJS6W2B;CHEBI:35261;SCHEMBL8020;DTXSID00943009;UXGVMFHEKMGWMA-UHFFFAOYSA-N;AKOS006370995;Q761117;208-83-3

Chemical Property of Isobenzofuran

Chemical Property:

• Vapor Pressure: 0.737mmHg at 25°C
• PSA: 13.14000
• LogP: 2.43280
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 118.041864811
• Heavy Atom Count: 9
• Complexity: 88.7

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC2=COC=C2C=C1
• General Description: Isobenzofuran derivatives, particularly α,β-unsaturated amides, have demonstrated significant immunosuppressive potential by inhibiting T-cell proliferation and IMPDH type II activity, with some compounds outperforming mycophenolic acid (MPA) in potency. These findings highlight their promise as safer and more effective immunosuppressive agents, warranting further investigation into their therapeutic applications and toxicity profiles.

Technology Process of Isobenzofuran

There total 3 articles about Isobenzofuran which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine (6321-72-8) + phthalide-3-carboxylic acid (708-14-5,62283-01-6,99266-05-4) → isobenzofuran (270-75-7) + 3-(10-methyl-9-phenyl-9,10-dihydroacridin-9-yl)isobenzofuran-1(3H)-one

Guidance literature:

In dichloromethane; for 0.5h; Heating;

Reference yield:

1-Ethoxy-1,3-dihydroisobenzofuran (75802-19-6) → isobenzofuran (270-75-7)

Guidance literature:

With lithium diisopropyl amide; In benzene;

DOI:10.1016/S0040-4039(00)94719-1

Reference yield:

9-methoxy-10-methyl-9-phenyl-9,10-dihydroacridine (99682-60-7) + phthalide-3-carboxylic acid (708-14-5,62283-01-6,99266-05-4) → isobenzofuran (270-75-7) + 3-(10-methyl-9-phenyl-9,10-dihydroacridin-9-yl)isobenzofuran-1(3H)-one

Guidance literature:

In dichloromethane; for 0.5h; Heating;

upstream raw materials:

1-Ethoxy-1,3-dihydroisobenzofuran

9-hydroxy-10-methyl-9-phenyl-9,10-dihydroacridine

phthalide-3-carboxylic acid

9-methoxy-10-methyl-9-phenyl-9,10-dihydroacridine

Downstream raw materials:

C₂₅H₂₅NO₂

1,4-dichlorophthalazine

1,3-diphenylisobenzofuran

Refernces

Synthesis and characterization of 1,3-diarylbenzo[c]selenophenes

10.1016/j.tet.2008.06.002

The study focuses on the synthesis and characterization of 1,3-diarylbenzo[c]selenophenes, which are conjugated macromolecules with potential applications due to their unique electrical and optical properties. The researchers used a selenium transfer reaction involving keto-alcohol/benzo[c]furan and Woollins reagent to synthesize a series of symmetrical and unsymmetrical 1,3-diarylbenzo[c]selenophenes. The chemicals used in the study include phthalides, aryl/hetero-arylmagnesium bromides, and Woollins reagent. Phthalides served as the starting materials, aryl/hetero-arylmagnesium bromides were used as Grignard reagents to open the ring of the phthalides, and Woollins reagent was employed as a selenium transfer agent to convert the intermediate keto-alcohols or benzo[c]furans into the target benzo[c]selenophenes. The purpose of these chemicals was to facilitate the formation of stable benzo[c]selenophene analogs, which were then studied for their optical and electrochemical properties to further understand their potential use in materials science, particularly in the development of electronic materials such as organic light-emitting diodes (OLEDs).

The design, synthesis and in vitro immunosuppressive evaluation of novel isobenzofuran derivatives

10.1016/j.bmcl.2011.11.078

The research aims to develop new compounds that could inhibit T-cell proliferation and IMPDH type II activity, with the aim of creating safer and more effective immunosuppressive drugs. The researchers synthesized a series of isobenzofuran-based compounds, including a,b-unsaturated amides, ureas, and diamides, and assessed their structure-activity relationships. The conclusions drawn from the study indicated that the a,b-unsaturated amide series generally demonstrated higher potency than the urea and diamide series, with compounds 2d, 2e, 2h, and 2j showing superior immunosuppressive properties compared to mycophenolic acid (MPA), a known immunosuppressive agent. Other compounds like 2k, 2m, 2n, 4c, and 5d exhibited inhibitory activity comparable to MPA. The study provided insights into the development of new immunosuppressive agents and further evaluation of these compounds is underway to determine their therapeutic potential and toxicity profiles.