2142-04-3

Basic information

• Product Name: 2-(4-METHOXY-PHENYL)-ISOINDOLE-1,3-DIONE
• Synonyms: 2-(4-METHOXY-PHENYL)-ISOINDOLE-1,3-DIONE;2-(4-METHOXYPHENYL)ISOINDOLINE-1,3-DIONE;2-(4-Methoxyphenyl)-2H-isoindole-1,3-dione;2-(4-methoxyphenyl)isoindoline-1,3-quinone
• CAS NO: 2142-04-3
• Molecular Formula: C₁₅H₁₁NO₃
• Molecular Weight: 253.25
• Mol File: 2142-04-3.mol
• Article Data: 67

Chemical Properties

• Melting Point: 162 °C
• Boiling Point: 443.1°C at 760 mmHg
• Flash Point: 221.8°C
• Appearance: /
• Density: 1.327g/cm³
• Vapor Pressure: 4.76E-08mmHg at 25°C
• Refractive Index: 1.64
• PKA: 0.18±0.20(Predicted)
• CAS DataBase Reference: 2-(4-METHOXY-PHENYL)-ISOINDOLE-1,3-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-METHOXY-PHENYL)-ISOINDOLE-1,3-DIONE(2142-04-3)
• EPA Substance Registry System: 2-(4-METHOXY-PHENYL)-ISOINDOLE-1,3-DIONE(2142-04-3)

Safety Data

• Hazardous Substances Data: 2142-04-3(Hazardous Substances Data)

Usage

General Description

2-(4-METHOXY-PHENYL)-ISOINDOLE-1,3-DIONE is a chemical compound with a molecular formula C16H11NO4. It is a derivative of isoindole-1,3-dione, a heterocyclic compound that contains both nitrogen and oxygen atoms in its ring structure. This specific derivative includes a 4-methoxy-phenyl group attached to the isoindole-1,3-dione core. It may be synthesized for use in organic chemistry research, pharmaceutical development, or other industrial applications. The compound's properties and potential uses will depend on its specific synthesis and intended application.

InChI:InChI=1/C15H11NO3/c1-19-11-8-6-10(7-9-11)16-14(17)12-4-2-3-5-13(12)15(16)18/h2-9H,1H3

Upstream product

• 85-44-9 phthalic anhydride 
• 104-94-9 4-methoxy-aniline 
• 3485-84-5 N-vinylphthalimide 
• 150-75-4 N-methyl-p-aminophenol 
• 131-11-3 phthalic acid dimethyl ester 
• 136918-14-4 phthalimide 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 57212-70-1 N-(mesyloxy)phthalimide 
• 100-66-3 methoxybenzene 
• 65441-03-4 4-(4-methoxy-phenyl)-2,3-benzoxazin-1-one 
• 368-39-8 triethyloxonium fluoroborate 
• 56530-39-3 N-p-tolylsulfonyloxyphthalimide 
• 615-42-9 1,2-Diiodobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 7554-80-5 N-(4'-methoxyphenyl)phthalamic acid 
• 77060-74-3 methyl 1,4-dihydroxy-2-naphthoate 
• 93818-09-8 3-ethyl-3-hydroxy-2-(4-methoxyphenyl)isoindolin-1-one 
• 7472-54-0 N-(p-methoxyphenyl)benzamide 

Relevant articles and documents

Chemical and electrochemical reduction of the products from the reactions of isoindolines and tetracyanoethylene

The reduction potentials of compounds resulting from the title reaction and containing one (4) or two (3) dicyanovinylidene moieties have been determined by means of cyclic voltammetry. Electrochemical reduction of the same compounds within the cavity of an EPR spectrometer led to the observation of radical species tentatively identified as the corresponding radical anions. EPR experiemnts have also provided indication that the first formed species in the butoxide reduction of 3 undergoes cleavage of the bond between the two heterocyclic systems evolving to radical anions identical to those obtained by similar reduction of compounds 4. Some models compounds have also been investigated for comparison purposes.

An Oxidation Study of Phthalimide-Derived Hydroxylactams

A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.

Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes

In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.

Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides

We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.