1072-87-3

Basic information

• Product Name: 3-methylpyrrole-2,5-dione
• Synonyms: 3-methylpyrrole-2,5-dione;citraconimide;3-methylpyrrole-2,5-dione（WS204337）
• CAS NO: 1072-87-3
• Molecular Formula: C₅H₅NO₂
• Molecular Weight: 111.1
• Mol File: 1072-87-3.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 237.8°Cat760mmHg
• Flash Point: 125.2°C
• Appearance: /
• Density: 1.248g/cm³
• Vapor Pressure: 0.0438mmHg at 25°C
• Refractive Index: 1.504
• CAS DataBase Reference: 3-methylpyrrole-2,5-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-methylpyrrole-2,5-dione(1072-87-3)
• EPA Substance Registry System: 3-methylpyrrole-2,5-dione(1072-87-3)

Safety Data

• Hazardous Substances Data: 1072-87-3(Hazardous Substances Data)

Usage

General Description

3-Methylpyrrole-2,5-dione, also known as 3-methylmaleimide, is a chemical compound with the molecular formula C5H5NO2. It is a white to off-white solid that is insoluble in water. 3-methylpyrrole-2,5-dione is used in the production of various polymers and resins, as well as in the synthesis of pharmaceuticals and agrochemicals. 3-Methylpyrrole-2,5-dione is also known for its use as a dienophile in the Diels-Alder reaction, a type of organic chemical reaction used to create cyclic compounds. It is important to handle this compound with care, as prolonged exposure or ingestion can cause irritation or harm to the respiratory system and skin, and it is considered toxic if swallowed or inhaled. Overall, 3-Methylpyrrole-2,5-dione has various industrial and chemical applications, but should be used with caution due to its potential hazards.

InChI:InChI=1/C5H5NO2/c1-3-2-4(7)6-5(3)8/h2H,1H3,(H,6,7,8)

Upstream product

• 81971-99-5 deuteroporphyrin IX dimethyl ester 
• 5522-66-7 3,3'-(3,7,12,17-tetramethyl-8,13-divinyl-21H,23H-porphine-2,18-diyl)-bis-propionic acid dimethyl ester 
• 26608-34-4 Etioporphyrin III 
• 2644-60-2 χ-phylloporphyrin-XV 
• 7564-40-1 N-carbamylcitraconimide 
• 616-02-4 citraconic acid anhydride 
• 498-23-7 citraconic acid 
• 6641-34-5 (3-methyl-2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-urea 
• 625-82-1 2,4-dimethyl-1H-pyrrole 

Downstream Products

• 73383-82-1 1-Benzyl-3-methyl-2,5-dihydropyrrole-2,5-dione 
• 84165-67-3 7-Carbamoyl-7-methyl-5-oxo-1,2,3,5,6,7-hexahydro-indolizine-8-carboxylic acid ethyl ester 
• 84165-61-7 (4-Methyl-2,5-dioxo-pyrrolidin-3-yl)-pyrrolidin-(2Z)-ylidene-acetic acid ethyl ester 
• 69636-49-3 2,3-dichloro-2-methylsuccinimide 
• 50656-76-3 (R)-(-)-5-hydroxy-3-methyl-3-pyrrolin-2-one 
• 940055-61-8 3-(2-aminobenzylamino)-3-methylpyrrolidine-2,5-dione 
• 150254-86-7 (+/-)-(E)-3-(4-Methoxyphenyl)-N-<4-(3-methyl-2,5-dioxo-1-pyrrolidinyl)butyl>-2-propenamide 
• 128866-07-9 (+/-)-(E)-3-(4-Hydroxyphenyl)-N-[4-(3-methyl-2,5-dioxo-1-pyrrolidinyl)butyl]-2-propenamide 
• 209802-54-0 (E)-pulchellalactam 
• 165606-93-9 3-(dichloromethylene)-4,4-dichloro-2,5-pyrrolidinedione 
• 339152-94-2 3-chloro-4-dichloromethyl-pyrrole-2,5-dione 
• 69636-50-6 3-chloro-4-methyl-1H-pyrrole-2,5-dione 
• 209802-54-0 (Z)-pulchellalactam 

Relevant articles and documents

Synthesis of aminal-type Lilium candidum alkaloids and lilaline; determination of their relative configuration by the concerted use of NMR spectroscopy and DFT conformational analysis

We hereby report the synthesis of six racemic alkaloids isolated from Lilium candidum L. Their common structural feature is a five-membered lactam ring which is, in the case of the flavonoid alkaloid lilaline, attached to the molecule's aromatic core, while in the case of the other five compounds, it is connected to the nitrogen atom of a pyrrolinone ring by an aminal function. The syntheses of these natural products were achieved via Mannich-type alkylations through cyclic N-acyliminium ions as intermediates. Besides the synthesis, the so far unexplored stereochemistry of these natural products was determined by a combination of NMR-based proton–proton distance measurements and theoretical conformational analyses carried out at the DFT level.

The first experimental demonstration of side chain extension of geoporphyrins in sediments

To investigate the formation process of high carbon number (>C 32) sedimentary porphyrins, heating experiments of several porphyrins were performed. Chromic acid oxidation of the heating products of protoporphyrin IX dimethyl ester afforded 2-methyl-3-npropylmaleimide as the predominant product among the side-chain extension products formed. On the other hand, saturated substituents of etioporphyrin were also extended on heating to slowly form normal and branched homologs. These results may suggest that the transalkylation of porphyrin side chains proceeds mainly by a regioselective mechanism involving alkyl radical addition to a vinyl group of chlorophylls or their diagenetic products.

Asymmetric bioreduction of C=C bonds using enoate reductases OPR1, OPR3 and YqjM: Enzyme-based stereocontrol

Three cloned enoate reductases from the "old yellow enzyme" family of flavoproteins were investigated in the asymmetric bioreduction of activated alkenes. 12-Oxophytodienoate reductase isoenzymes OPR1 and OPR3 from Lycopersicon esculentum (tomato), and YqjM from Bacillus subtilis displayed a remarkably broad substrate spectrum by reducing α,β-unsaturated aldehydes, ketones, maleimides and nitroalkenes. The reaction proceeded with absolute chemoselectivity-only the conjugated C=C bond was reduced, while isolated olefins and carbonyl groups remained intact-with excellent stereoselectivities (ees up to >99%). Upon reduction of a nitroalkene, the stereochemical outcome could be determined via choice of the appropriate enzyme (OPR1 versus OPR3 or YqjM), which furnished the corresponding enantiomeric nitroalkanes in excellent ee. Molecular modelling suggests that this "enzyme-based stereocontrol" is caused by subtle differences within the active site geometries.