83039-57-0

Basic information

• Product Name: 2,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-
• CAS NO: 83039-57-0
• Molecular Formula: C12H11NO4
• Molecular Weight: 233.224
• Mol File: 83039-57-0.mol

Chemical Properties

• CAS DataBase Reference: 2,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-(83039-57-0)
• EPA Substance Registry System: 2,5-Pyrrolidinedione, 1-[(4-methylbenzoyl)oxy]-(83039-57-0)

Safety Data

• Hazardous Substances Data: 83039-57-0(Hazardous Substances Data)

Upstream product

• 17592-54-0 2,5-dioxopyrrolidin-1-yl formate 
• 624-31-7 4-tolyl iodide 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 104-87-0 4-methyl-benzaldehyde 
• 1634-04-4 tert-butyl methyl ether 
• 99-94-5 p-Toluic acid 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 814-49-3 diethyl chlorophosphate 
• 589-18-4 4-Methylbenzyl alcohol 
• 201230-82-2 carbon monoxide 
• 29540-83-8 p-tolyl triflate 

Downstream Products

• 5456-97-3 N-butyl-4-methylbenzamide 
• 2318-82-3 N-hydroxy-4-methylbenzamide 
• 5436-83-9 N-benzyl-4-methylbenzamide 
• 1415816-84-0 C₃₄H₃₆N₄O₆ 
• 1165802-20-9 C₄₁H₄₀N₂O₃ 

Relevant articles and documents

N -Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines via the tandem N -hydroxysuccinimide ester formation

A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which facilely converted into amides in one pot. In addition, the drug moclobemide was synthesized to represent the practical utility of the developed methodology. This journal is

Formation of 1-hydroxymethylene-1,1-bisphosphinates through the addition of a silylated phosphonite on various trivalent derivatives

An easily handled one-pot synthetic procedure was previously developed for the synthesis of bisphosphinates starting from acyl chlorides. Herein, other trivalent derivatives as acid anhydrides and activated esters were tested to form various bisphosphinates. This modulation of the reactivity can be controlled according to the nature of the acid derivative for the use of sensitive and functionalized substrates.

N-Doped Yellow TiO2 Hollow Sphere-Mediated Visible-Light-Driven Efficient Esterification of Alcohol and N-Hydroxyimides to Active Esters

Herein we report a simple synthetic protocol for N-doped yellow TiO2 (N-TiO2) hollow spheres as an efficient visible-light-active photocatalyst using aqueous titanium peroxocarbonate complex (TPCC) solution as precursor and NH4OH. In the developed strategy, the ammonium ion of TPCC and NH4OH acts as nitrogen source and structure-directing agent. The synthesized N-TiO2 hollow spheres are capable of promoting the synthesis of active esters of N-hydroxyimide and alcohol through simultaneous selective oxidation of alcohol to aldehyde followed by cross-dehydrogenative coupling (CDC) under ambient conditions upon irradiation of visible light. It is possible to develop a novel and cost-effective one-pot strategy for the synthesis of important esters and amides on gram scale using the developed strategy. The catalytic activity of N-TiO2 hollow spheres is much superior to that of other reported N-TiO2 samples as well as TiO2 with varying morphology.

Metal-Free C(sp3)-H Allylation via Aryl Carboxyl Radicals Enabled by Donor-Acceptor Complex

The first aryl carboxyl radical generation by the donor-acceptor complex with N-acyloxyphthalimides and Hantzsch esters is reported. Regio- and chemoselective C(sp3)-H bond allylation is enabled by aryl carboxyl radicals with visible light irradiation under mild and metal-free conditions.

Atmospheric oxidative catalyst-free cross-dehydrogenative coupling of aldehydes with N-hydroxyimides

Cross-dehydrogenative coupling (CDC) reactions of aldehydes with N-hydroxyimidates such as N-hydroxysuccinimide (NHSI), N-hydroxyphthalimide (NHPI) under catalyst-free conditions is described. Moreover, the desired products can be obtained simply by recrystallization from ethanol. This method is also applicable to the synthesis of amides in excellent yields. A radical mechanism of the type shown in Scheme 4 is proposed based upon the inhibition of the reaction in the presence of TEMPO.

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.

Metal-free intermolecular C-O cross-coupling reactions: Synthesis of: N -hydroxyimide esters

Selectfluor-mediated intermolecular C-O cross coupling reaction for the synthesis of N-hydroxyimide esters was developed for the first time. The reaction is applicable to the coupling of readily available aryl and alkyl aldehydes with N-hydroxyphthalimide (NHPI) and N-hydroxysuccinimide (NHSI). The resulting active esters can be directly converted into amides in one pot.

Palladium-Catalyzed Carbonylation of (Hetero)Aryl, Alkenyl and Allyl Halides by Means of N-Hydroxysuccinimidyl Formate as CO Surrogate

An efficient Pd-catalyzed carbonylation protocol is described for the coupling of a large panel of aryl, heteroaryl, benzyl, vinyl and allyl halides 2 with the unusual N-hydroxysuccinimidyl (NHS) formate 1 as a CO surrogate to afford the corresponding valuable NHS esters 3. High conversion to the coupling products was achieved with up to 98% yield by means of Pd(OAc)2/Xantphos catalyst system.

Cross dehydrogenative coupling (CDC) of aldehydes with N-hydroxyimides by visible light photoredox catalysis

A photoinduced cross-dehydrogenative-coupling (CDC) reaction between aldehydes and N-hydroxyimides has been developed for the synthesis of ester derivatives. Using 2 mol% [Ru(bpy)3]Cl2 in dry acetonitrile at room temperature with an LED light bulb, we were able to synthesize N-hydroxyesters in good yields. The ester derivatives are very useful synthetic intermediates, which were transformed to amide and oxazole building blocks in excellent yields. This journal is

One-pot synthesis of hydroxamic acids from aldehydes and hydroxylamine

A one-pot oxidative transformation of aldehydes into hydroxamic acids by the use of an aqueous solution of hydroxylamine is reported. The methodology gives high yields and makes use of cheap, abundant and easily available reagents.