211501-36-9

Basic information

• Product Name: 1H-Isoindole-1,3(2H)-dione,2-(2-hydroxy-1-methylethyl)-
• Synonyms: 2-(2-HYDROXY-1-METHYLETHYL)-1H-ISOINDOLE-1,3(2H)-DIONE
• CAS NO: 211501-36-9
• Molecular Formula: C₁₁H₁₁NO₃
• Molecular Weight: 205.20994
• Mol File: 211501-36-9.mol
• Article Data: 10

Chemical Properties

• Melting Point: 99-101℃
• Boiling Point: 357℃
• Flash Point: 170℃
• Appearance: /
• Density: 1.348
• Solubility: Chloroform; Methanol; DMSO
• CAS DataBase Reference: 1H-Isoindole-1,3(2H)-dione,2-(2-hydroxy-1-methylethyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Isoindole-1,3(2H)-dione,2-(2-hydroxy-1-methylethyl)-(211501-36-9)
• EPA Substance Registry System: 1H-Isoindole-1,3(2H)-dione,2-(2-hydroxy-1-methylethyl)-(211501-36-9)

Safety Data

• Hazardous Substances Data: 211501-36-9(Hazardous Substances Data)

Usage

Description

1H-Isoindole-1,3(2H)-dione,2-(2-hydroxy-1-methylethyl)-, also known as 2-(1-Hydroxypropan-2-yl)isoindoline-1,3-dione, is an organic compound that serves as a crucial intermediate in the synthesis of various pharmaceutical compounds. It is characterized by its unique chemical structure, which includes an isoindoline core with a hydroxypropyl side chain and a dione functional group.

Uses

Used in Pharmaceutical Synthesis:
1H-Isoindole-1,3(2H)-dione,2-(2-hydroxy-1-methylethyl)is used as an intermediate in the synthesis of m-Hydroxy Mexiletine (H939030), a metabolite of Mexiletine (M340800). Mexiletine is a class Ib antiarrhythmic drug that is used to treat certain types of abnormal heart rhythms, such as ventricular arrhythmias. The compound plays a vital role in the development of this drug, contributing to its therapeutic effects and potential applications in the treatment of cardiac conditions.
In the pharmaceutical industry, 1H-Isoindole-1,3(2H)-dione,2-(2-hydroxy-1-methylethyl)is used as a key building block for the synthesis of other bioactive molecules and drug candidates. Its unique chemical structure allows for further functionalization and modification, enabling the development of new drugs with improved pharmacological properties and therapeutic potential.

Upstream product

• 85-44-9 phthalic anhydride 
• 6168-72-5 2-Amino-1-propanol 
• 3485-84-5 N-vinylphthalimide 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1158349-31-5 (+/-)-O-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl] 4-chlorophenyl(3-nitrobenzoyl)thiocarbamate 
• 1252084-89-1 2-[2-(3-methoxyphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione 
• 1228017-24-0 C₁₇H₁₃Cl₂NO₃ 
• 1161742-03-5 (+/-)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl 2,5-difluorobenzoate 
• 1237512-75-2 2-{2-[2,6-bis(hydroxymethyl)phenoxy]-1-methylethyl}-1H-isoindole-1,3(2H)-dione 
• 1237512-78-5 2-[2-(4-acetyl-2,6-dimethylphenoxy)-1-methylethyl]-1H-isoindole-1,3(2H)-dione 
• 1237512-79-6 4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]-3,5-dimethylphenyl acetate 
• 1237512-80-9 3-(bromomethyl)-4-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propoxy]-5-methylphenyl acetate 
• 1237512-81-0 2-{2-[4-hydroxy-2-(hydroxymethyl)-6-methylphenoxy]-1-methylethyl}-1H-isoindole-1,3(2H)-dione 
• 1237512-74-1 2-{2-[2,6-bis(bromomethyl)phenoxy]-1-methylethyl}-1H-isoindole-1,3(2H)-dione 
• 1445-69-8 2,3-dihydrophthalazine-1,4-dione 
• 1356451-99-4 C₁₉H₁₈ClNO₃ 
• 1620514-75-1 2-(1-(tritylthio)propan-2-yl)isoindoline-1,3-dione 

Relevant articles and documents

Dual Rh?Ru Catalysts for Reductive Hydroformylation of Olefins to Alcohols

An active and selective dual catalytic system to promote domino hydroformylation–reduction reactions is described. Apart from terminal, di- and trisubstituted olefins, for the first time the less active internal C?C double bond of tetrasubstituted alkenes can also be utilized. As an example, 2,3-dimethylbut-2-ene is converted into the corresponding n-alcohol with high yield (90 %) as well as regio- and chemoselectivity (>97 %). Key for this development is the use of a combination of Rh complexes with bulky monophosphite ligands and the Ru-based Shvo's complex. A variety of aromatic and aliphatic alkenes can be directly used to obtain mainly linear alcohols.

Synthesis and toxicopharmacological evaluation of m-Hydroxymexiletine, the first metabolite of mexiletine more potent than the parent compound on voltage-gated sodium channels

The first synthesis of m-hydroxymexiletine (MHM) has been accomplished. MHM displayed hNav1.5 sodium channel blocking activity, and tests indicate it to be ～2-fold more potent than the parent mexiletine and to have more favorable toxicological properties than mexiletine. Thus, MHM and possible related prodrugs might be studied as agents for the treatment of arrhythmias, neuropathic pain, and myotonias in substitution of mexiletine (metabolite switch), which has turned out to be tainted with common toxicity.

Design, synthesis, and pharmacological effects of structurally simple ligands for MT1 and MT2 melatonin receptors

A series of phenoxyalkyl and phenylthioalkyl amides were prepared as melatoninergic ligands. Modulation of affinity of the newly synthesized compound by applying SARs around the terminal amide moiety, the alkyl chain, and the methoxy group on the aromatic ring provides compounds with nanomolar affinity for both melatonin receptor subtypes. Affinity towards MT1 and MT2 receptors were modulated also exploiting chirality. The investigation of intrinsic activity revealed that all the tested compounds behave as full or partial agonists.