93282-20-3

Basic information

• Product Name: 5-METHYLISOINDOLINE
• Synonyms: 5-METHYLISOINDOLINE;2,3-dihydro-5-methyl-1H-Isoindole;5-Methylisoindoline Hydrochloride;5-Methylisoindoline(WX604540)
• CAS NO: 93282-20-3
• Molecular Formula: C₉H₁₁N
• Molecular Weight: 133.19
• Mol File: 93282-20-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-METHYLISOINDOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-METHYLISOINDOLINE(93282-20-3)
• EPA Substance Registry System: 5-METHYLISOINDOLINE(93282-20-3)

Safety Data

• Hazardous Substances Data: 93282-20-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-Methylisoindoline is used as a key intermediate in the synthesis of various pharmaceutical compounds for its unique reactivity and structural properties. It plays a crucial role in the development of new drugs and medicines, contributing to advancements in healthcare and medical treatments.
Used in Agrochemical Industry:
5-Methylisoindoline is used as a building block in the synthesis of agrochemicals, such as pesticides and herbicides. Its unique properties allow for the creation of effective and targeted agricultural chemicals, enhancing crop protection and contributing to increased agricultural productivity.
Used in Research and Development:
5-Methylisoindoline is used as a valuable chemical in scientific research and development, particularly in the fields of medicine and agriculture. Its potential applications are being explored through various research studies, leading to the discovery of new compounds and advancements in these industries.
Used in Organic Synthesis:
5-Methylisoindoline is used as a versatile building block in organic synthesis due to its unique reactivity and structural properties. It enables the preparation of a wide range of compounds, contributing to the development of new materials and chemical processes.
Used in Chemical Production:
5-Methylisoindoline is used in the production of various chemical compounds, leveraging its stability, solubility, and unique properties. Its application in chemical production contributes to the creation of new products and the improvement of existing ones, driving innovation and progress in the chemical industry.

Upstream product

• 19438-61-0 4-methylphthalic anhydride 
• 40314-06-5 5-methyl-1H-isoindole-1,3-(2H)-dione 

Relevant articles and documents

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.

Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization

An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.

Inhibitors of dipeptidyl peptidase 8 and dipeptidyl peptidase 9. Part 2: Isoindoline containing inhibitors

To obtain selective and potent inhibitors of dipeptidyl peptidases 8 and 9, we synthesized a series of substituted isoindolines as modified analogs of allo-Ile-isoindoline, the reference DPP8/9 inhibitor. The influence of phenyl substituents and different P2 residues on the inhibitors' affinity toward other DPPs and more specifically, their potential to discriminate between DPP8 and DPP9 will be discussed. Within this series compound 8j was shown to be a potent and selective inhibitor of DPP8/9 with low activity toward DPP II.

Substituted pyrrolidine-2,4-dicarboxylic acid amides as potent dipeptidyl peptidase IV inhibitors

A series of substituted pyrrolidine-2,4-dicarboxylic acid amides were synthesized as potential antidiabetic agents, and many of them showed good in vitro DPP-IV inhibition (IC50 = 2-250 nM) with selectivity over DPP-II, DPP8, and FAP enzymes. Selected compounds 8c and 11a showed in vivo plasma DPP-IV inhibition after oral administration in Wistar rats.

COMPOUND INHIBITING DIPEPTIDYL PEPTIDASE IV

The invention aims to provide a dipeptidyl peptidase IV inhibitor which is satisfactory in respect of activity, stability and safety and has an excellent action as a pharmaceutical agent. The invention is directed to a compound represented by the following general formula or a pharmaceutically acceptable salt thereof: wherein R1 and R2 each represents hydrogen, an optionally substituted C1-6 alkyl group, or -COOR5 whereupon R5 represents hydrogen or an optionally substituted C1-6 alkyl group, or R1 and R2, together with a carbon atom to which they are bound, represent a 3- to 6-membered cycloalkyl group, R3 represents hydrogen or an optionally substituted C6-10 aryl group, R4 represents a hydrogen or a cyano group, D represents -CONR6-, -CO- or -NR6CO-, R6 represents hydrogen or an optionally substituted C1-6 alkyl group, E represents -(CH2)m- whereupon m is an integer of 1 to 3, -CH2OCH2-, or -SCH2-, n is an integer of 0 to 3, and A represents an optionally substituted bicyclic heterocyclic group or bicyclic hydrocarbon group.