67695-80-1

Usage

Physical appearance

White to off-white crystalline powder
The compound appears as a white to off-white crystalline powder, which is a common form for many organic compounds.
4. High melting point
1H-Isoindole-1,3(2H)-dione, 2-[(4-methoxybenzoyl)oxy]has a high melting point, indicating that it requires a significant amount of heat to transition from a solid to a liquid state.

Solubility

Soluble in organic solvents such as acetone and ethanol
The compound dissolves easily in organic solvents like acetone and ethanol, which is important for its use in various chemical reactions and applications.

Uses

Acylation of various compounds, production of pharmaceuticals and agrochemicals
1H-Isoindole-1,3(2H)-dione, 2-[(4-methoxybenzoyl)oxy]is used in the laboratory for the acylation of different compounds, which is a chemical reaction that involves the transfer of an acyl group. It is also utilized in the production of pharmaceuticals and agrochemicals, making it an important intermediate in the synthesis of various active ingredients.

Safety precautions

Respiratory and skin irritation, harmful if swallowed or inhaled
When handling 1H-Isoindole-1,3(2H)-dione, 2-[(4-methoxybenzoyl)oxy]-, it is crucial to take safety precautions, as it may cause respiratory and skin irritation. Additionally, the compound is harmful if swallowed or inhaled, so proper protective measures should be followed to minimize exposure and potential health risks.

Upstream product

• 524-38-9 N-hydroxyphthalimide 
• 105-13-5 4-Methoxybenzyl alcohol 
• 100-07-2 4-methoxy-benzoyl chloride 
• 104-93-8 p-methylanizole 
• 100-09-4 4-methoxybenzoic acid 
• 123-11-5 4-methoxy-benzaldehyde 

Downstream Products

• 520-03-6 N-phenylphthalimide 
• 611-94-9 4-Methoxybenzophenone 
• 66938-29-2 (2-fluorophenyl)(4-methoxyphenyl)methanone 
• 5449-69-4 2,4'-dimethoxybenzophenone 
• 54118-78-4 4'-methoxy-3-nitro-benzophenone 
• 171364-79-7 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 
• 1620767-23-8 tetrahydrofuran-2-yl 4-methoxybenzoate 
• 4181-97-9 phenyl 4-methoxybenzoate 

Relevant academic research and scientific papers

tert-Butyl Nitrite as a Twofold Hydrogen Abstractor for Dehydrogenative Coupling of Aldehydes with N-Hydroxyimides

A synthetically practical transition metal/catalyst/halogen-free dehydrogenative coupling of aldehydes with N-hydroxyimides promoted solely by tert-butyl nitrite under mild conditions was developed. tert-Butyl nitrite generates two radicals (tBuO and NO) and thus works as a twofold hydrogen abstractor. A diverse array of N-hydroxyimide esters were prepared from either aliphatic or aromatic aldehydes. Benzoyl-substituted aldehydes such as 2-oxo-2-phenylacetaldehyde are also suitable.

Visible Light-Driven Efficient Synthesis of Amides from Alcohols using Cu?N?TiO2 Heterogeneous Photocatalyst

Amides were synthesized from alcohols and amines in high yields using an in situ generated active ester of N-hydroxyimide with our developed Cu?N?TiO2 catalyst at room temperature using oxygen as a sole oxidant under visible light. The catalyst can be easily prepared, robust, and recycled four times without a considerable change in catalytic activity. This developed protocol applies to a wide substrate scope and has good functional group tolerance. The application of this amidation reaction has been successfully demonstrated for the synthesis of moclobemide, an antidepressant drug, and an analog of the itopride drug on a gram scale.

Nickel-Catalyzed Cross-Coupling of Aryl Redoxactive Esters with Aryl Zinc Reagents

A nickel-catalyzed aryl-aroyloxyl C(sp2)-O radical cross-coupling reaction conducted using a redox active ester with aryl zinc reagent was developed. This method demonstrates a new disconnection approach for formation of aryl aryl esters. In the one-pot sequential process, the readily available aryl carboxylic acids can be converted into functionalized aryl aryl esters and heteroaryl esters. This protocol is amenable to the gram-scale synthesis. The present method has a wide substrate scope and high functional group tolerance.

A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides by a TiO2-Co ascorbic acid nanohybrid under visible light irradiation

In this study, we performed a visible light-mediated aerobic photo-cross dehydrogenative coupling (CDC) reaction between aldehydes and N-hydroxyimides using TiO2-AA-Co as a photocatalyst for the synthesis of active esters. The synergistic and selective effects of the cobalt ascorbic acid complex (Co-AA) and TiO2 nanoparticles on the visible-light photocatalytic activity were explored. The method possesses some advantages such as environmentally friendly conditions, easy work-up procedure, reusability, and scalability.

Ferric nitrate-promoted oxidative esterification of toluene with N-hydroxyphthalimide: Synthesis of N-hydroxyimide esters

A ferric nitrate-promoted cross-dehydrogenative coupling reaction of N-hydroxyphthalimide (NHPI) with toluene derivatives is reported. The reaction proceeded smoothly using molecular oxygen as an oxidant, providing an efficient method for the synthesis of

Iron-Nitrate-Catalyzed Oxidative Esterification of Aldehydes and Alcohols with N-Hydroxyphthalimide: Efficient Synthesis of N-Hydroxyimide Esters

An Fe(NO3)3·9H2O-catalyzed cross-dehydrogenative coupling reaction between N-hydroxyphthalimide (NHPI) or N-hydroxysuccinimide (NHSI) and aldehydes or alcohols in air is described. This transformation represents an efficient approach to the preparation of N-hydroxyimide ester derivatives in moderate to excellent yields, and has a wide substrate scope.

Copper-Catalyzed Highly Efficient Esterification of Aldehydes with N -Hydroxyphthalimide via Cross-Dehydrogenative Coupling in Water at Room Temperature

A copper-catalyzed cross-dehydrogenative coupling reaction between N -hydroxyphthalimide and aldehydes using PhI(OAc) 2 as an oxidant is described. It is reported for the first time to synthesize NHPI esters in water, providing the corresponding NHPI esters in moderate to good yields. This facile and efficient method is eco-friendly and possesses the advantages of mild conditions, short reaction time, and broad substrate scope.

Isonicotinate Ester Catalyzed Decarboxylative Borylation of (Hetero)Aryl and Alkenyl Carboxylic Acids through N-Hydroxyphthalimide Esters

Decarboxylative borylation of aryl and alkenyl carboxylic acids with bis(pinacolato)diboron was achieved through N-hydroxyphthalimide esters using tert-butyl isonicotinate as a catalyst under base-free conditions. A variety of aryl carboxylic acids possessing different functional groups and electronic properties can be smoothly converted to aryl boronate esters, including those that are difficult to decarboxylate under transition-metal catalysis, offering a new method enabling use of carboxylic acid as building blocks in organic synthesis. Mechanistic analysis suggests the reaction proceeds through coupling of a transient aryl radical generated by radical decarboxylation with a pyridine-stabilized persistent boryl radical. Activation of redox active esters may proceed via an intramolecular single-electron-transfer (SET) process through a pyridine-diboron-phthalimide adduct and accounts for the base-free reaction conditions.

Transition-Metal-Free, Visible-Light-Enabled Decarboxylative Borylation of Aryl N-Hydroxyphthalimide Esters

Herein, we report a conceptually novel borylation reaction proceeding via a mild photoinduced decarboxylation of redox-activated aromatic carboxylic acids. This work constitutes the first application of cheap and easily prepared N-hydroxyphthalimide esters as aryl radical precursors and does not require the use of expensive transition metals or ligands. The reaction is operationally simple, scalable, and displays broad scope and functional group tolerance.