17616-03-4

Basic information

• Product Name: 1-DODECYL-PYRROLE-2,5-DIONE
• Synonyms: N-LAURYLMALEIMIDE;N-DODECYL MALEIMIDE;1-dodecyl-1h-pyrrole-5-dione;5-dione,1-dodecyl-1H-Pyrrole-2;1-DODECYL-PYRROLE-2,5-DIONE;N-Dodecylmaleinimide;1H-Pyrrole-2,5-dione, 1-dodecyl-;1-Dodecyl-3-pyrroline-2,5-dione
• CAS NO: 17616-03-4
• Molecular Formula: C₁₆H₂₇NO₂
• Molecular Weight: 265.39
• Product Categories: pharmacetical
• Mol File: 17616-03-4.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 371.9 °C at 760 mmHg
• Flash Point: 142 °C
• Appearance: /
• Density: 0.987 g/cm³
• Vapor Pressure: 9.95E-06mmHg at 25°C
• Refractive Index: 1.488
• CAS DataBase Reference: 1-DODECYL-PYRROLE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-DODECYL-PYRROLE-2,5-DIONE(17616-03-4)
• EPA Substance Registry System: 1-DODECYL-PYRROLE-2,5-DIONE(17616-03-4)

Safety Data

• Statements: 20/21/22-36/37/38
• Safety Statements: 26-27-36/37/39
• Hazardous Substances Data: 17616-03-4(Hazardous Substances Data)

Usage

General Description

1-Dodecyl-pyrrole-2,5-dione is a chemical compound that belongs to the class of organic compounds known as pyrrole-2,5-diones. These compounds contain a pyrrole ring, which is a five-membered aromatic heterocycle, bearing a keto group at the 2-position and another one at the 5-position. The 1-dodecyl-pyrrole-2,5-dione is specifically characterized by a long-chain dodecyl group attached to the nitrogen atom of the pyrrole ring. The specific applications and uses of this chemical can typically be found within scientific and industrial research, as it has been used in various chemical reactions, but detailed information about its physical properties or toxicity is not readily available.

InChI:InChI=1/C16H27NO2/c1-2-3-4-5-6-7-8-9-10-11-14-17-15(18)12-13-16(17)19/h12-13H,2-11,14H2,1H3

Upstream product

• 108-31-6 maleic anhydride 
• 124-22-1 n-Dodecylamine 
• 52492-69-0 (Z)-4-(dodecylamino)-4-oxobut-2-enoic acid 
• 488737-41-3 C₂₀H₃₁NO₃ 
• 100581-97-3 maleic dodecylamide 

Downstream Products

• 111024-67-0 3-(3,5-di-t-butyl-4-hydroxyphenyl)-1-n-dodecylpyrrolidine-2,5-dione 
• 111024-68-1 3-(3-t-butyl-4-hydroxy-5-methylphenyl)-1-n-dodecylpyrrolidine-2,5-dione 
• 92176-77-7 3-(3,5-di-t-butyl-4-hydroxyphenylthio)-1-n-dodecylpyrrolidine-2,5-dione 
• 1313866-08-8 N,N'-bis-n-dodecyl-1,5-bis(3,5-bis(octyloxy)phenyl)anthracene-2,3,6,7-bisimide 
• 1313866-13-5 N,N-bis-n-dodecyl-5,12-bis(3,5-bis(1-octyloxy)phenyl)pentacene-2,3,9,10-bisimide 
• 1313866-17-9 N,N'-bis-n-dodecyl-1,6-bis(3,5-bis(1-octyloxy)phenyl)tetracene-2,3,8,9-bisimide 
• 1316216-68-8 2,3-bis(biphenyl-4-yl)-N-dodecylmaleimide 
• 1316216-62-2 2,3-diphenyl-N-dodecylmaleimide 
• 1316216-66-6 2-(biphenyl-4-yl)-N-dodecylmaleimide 

Relevant articles and documents

Efficient synthesis of isoxazolidine-tethered monolayer-protected gold nanoparticles (MPGNs) via 1,3-dipolar cycloadditions under high-pressure conditions

(Chemical Equation Presented) A maleimide-modified 2.5 ± 0.5 nm mixed monolayer protected gold nanoparticle (2-C12MPGN) containing approximately 30% maleimide-terminated dodecanethiolate/dodecanethiolate ligands was prepared. The 2-C12MPGN was reacted with a series of nitrones (a-i) at both atmospheric and hyperbaric (11 000 atm) conditions to form the corresponding isoxazolidine-modified nanoparticles (3-C12MPGN) via an interfacial 1,3-dipolar cycloaddition. At atmospheric pressures, the reaction proceeds slowly (if at all) and makes this reaction impractical for the synthetic modification of the nanoparticles. However, by performing the reaction under the high-pressure conditions, the reaction proceeds efficiently and quantitatively. TEM shows that the use of high pressure does not affect the size of the gold nanoparticle core. The 3-C12MPGNs were characterized by 1H NMR spectroscopy by comparing the spectra obtained with those of model reactions utilizing N-dodecylmaleimide (4) with the same nitrones (a-i) to form 5. Additionally, the cycloaddition reaction also occurs more readily with 4 than with 2-C12MPGN with all nitrones, indicating that the environment of the latter affects the cycloaddition reaction.

A fluorescence "turn-on" ensemble for acetylcholinesterase activity assay and inhibitor screening

By making use of the aggregation-induced emission feature of compound 1 and the cascade reactions among acetylthiocholine iodide (ATC), AChE, and compound 2, a new fluorescence "turn-on" method is developed for AChE assay and inhibitor-screening.

MANUFACTURING METHOD OF N-SUBSTITUTED MALEIMIDE

PROBLEM TO BE SOLVED: To provide a manufacturing method of N-substituted maleimide which can manufacture the N-substituted maleimide having long-chain alkyl groups efficiently even if amine having long-chain alkyl groups are used as a raw material. SOLUTION: A manufacturing method of N-substituted maleimide includes a step reacting maleic anhydride and amine in a solvent mixture containing aromatic organic solvent and alicyclic organic solvent and/or aliphatic organic solvent which carbon number is 8-18. SELECTED DRAWING: None COPYRIGHT: (C)2018,JPOandINPIT

Study of the diels-alder and retro-diels-alder reaction between furan derivatives and maleimide for the creation of new materials

The Diels-Alder reaction leads to a mixture of two diastereomers, one called endo and the other one exo. The cyclo-reversion temperature of the first one is lower than the exo adduct and the ratio between endo and exo adducts varies according to the substituents of the Diels-Alder partners and experimental parameters. Therefore, the influence of some reaction parameters such as the substituents of furan and maleimide derivatives, the reaction temperature and the presence of a nucleophile on the endo/exo Diels-Alder ratio and/or the retro-Diels-Alder reaction have been studied. For instance, furan and maleimide derivatives with electron withdrawing substituents induced the creation of the endo adduct preferentially. Also the presence of a far electron withdrawing substituent on furan and/or an electron attracting mesomeric substituent on maleimide resulted in a faster reversibility of the endo adduct. Finally, a high temperature and the presence of a nucleophile (thiol) also induced faster retro-Diels-Alder kinetics. Moreover, it was proved that isomerization from the endo to the exo diastereomer is preceded by a retro-Diels-Alder reaction of the endo adduct. The presence of a nucleophile in the mixture confirmed this result. This study allowed the highlighting of different parameters of the Diels-Alder reaction to obtain as much endo adduct as possible, and a fast and/or full retro-Diels-Alder reaction of this adduct.