4030-22-2

Basic information

• Product Name: 3,4-DIMETHYL-2,5-DIHYDRO-1H-PYRROL-2-ONE
• Synonyms: 1,5-Dihydro-3,4-dimethyl-2H-pyrrol-2-one;3,4-Dimethyl-3-pyrrolin-2-one;3,4-Dimethyl-1,5-dihydro-2H-pyrrol-2-one;3,4-Dimethyl-3-pyrrolin-2-one, 2,5-Dihydro-3,4-dimethyl-2-oxo-1H-pyrrole
• CAS NO: 4030-22-2
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.1447
• Mol File: 4030-22-2.mol
• Article Data: 11

Chemical Properties

• Melting Point: 125 °C
• Appearance: /
• CAS DataBase Reference: 3,4-DIMETHYL-2,5-DIHYDRO-1H-PYRROL-2-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-DIMETHYL-2,5-DIHYDRO-1H-PYRROL-2-ONE(4030-22-2)
• EPA Substance Registry System: 3,4-DIMETHYL-2,5-DIHYDRO-1H-PYRROL-2-ONE(4030-22-2)

Safety Data

• Hazardous Substances Data: 4030-22-2(Hazardous Substances Data)

Usage

General Description

3,4-DIMETHYL-2,5-DIHYDRO-1H-PYRROL-2-ONE is a chemical compound with the molecular formula C7H11NO. It is a cyclic amide with a pyrrolidine core, and its structure consists of a pyrrole ring with two methyl groups and a carbonyl group. 3,4-DIMETHYL-2,5-DIHYDRO-1H-PYRROL-2-ONE is commonly used as a building block in organic synthesis and medicinal chemistry, and it exhibits a range of biological activities. It has been identified as a potential inhibitor of acetylcholinesterase, an enzyme that catalyzes the breakdown of the neurotransmitter acetylcholine in the nervous system. Additionally, 3,4-DIMETHYL-2,5-DIHYDRO-1H-PYRROL-2-ONE has been investigated for its potential as a drug for treating Alzheimer's disease and other neurodegenerative disorders.

Upstream product

• 822-51-5 3,4-dimethyl-1H-pyrrole 
• 19713-89-4 3,4-dimethylpyrrole-2-carboxaldehyde 
• 89776-55-6 3,4-dimethyl-1H-pyrrole-2-carboxylic acid 
• 938-75-0 3,4-dimethyl-1H-pyrrole-2-carboxylic acid ethyl ester 
• 61491-71-2 3-cyano-3-hydroxy-2-methyl-butyric acid ethyl ester 
• 513-81-5 2,3-dimethyl-buta-1,3-diene 
• 17875-29-5 2-ethoxycarbonyl-3,6-dihydro-4,5-dimethyl-1,2-thiazine 1-oxide 
• 910032-50-7 N-methoxy-N-methyl-3,4-dimethylpyrrole-2-carboxamide 
• 100383-27-5 3,4-Dimethyl-1-acetyl-Δ³-pyrrolon-(2) 

Downstream Products

• 64576-54-1 Z-3,4-dimethyl-5-(2-pyridylmethylidene)-3-pyrrolin-2-one 
• 1605312-07-9 (2R,5S)-5-(3,4-dimethyl-2-oxo-2,5-dihydro-pyrrol-1-ylmethyl)-4-{2-[6-(4-fluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester 
• 135570-18-2 (1R,2R)-trans-cyclohexanediol bis<2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one-9-carboxylate> 
• 135570-19-3 (1R,2R)-trans-cyclohexanediol mono<2,3,7,8-tetramethyl-(10H)-dipyrrin-1-one-9-carboxylate> 
• 85870-74-2 E-3,4-dimethyl-5-(phenylmethylidene)-3-pyrrolin-2-one 
• 157670-02-5 1,3-phenyldimethyl-bis-(2-<(1,5-dideoxy-3,4-dimethyl-5-oxo-2H-pyrrole-2-ylidene methyl)-4-methyl-1H-pyrrole-3-propanoic acid dimethyl ester>) 
• 157670-03-6 1,4-phenyldimethyl-bis-(2-<5-(1,5-dideoxy-3,4-dimethyl-5-oxo-2H-pyrrole-2-ylidene methyl)-4-methyl-1H-pyrrole-3-propanoic acid dimethyl ester>) 
• 89053-39-4 (Z)-3,4-dimethyl-5-(4-methoxycarbonylphenylmethylene)-3-pyrrolin-2-one 
• 85057-79-0 (Z)-5-<(4-methoxyphenyl)methylene>-3,4-dimethyl-3-pyrrolin-2-one 
• 85870-73-1 Z-3,4-dimethyl-5-(phenylmethylidene)-3-pyrrolin-2-one 
• 61809-98-1 5-(4-dimethylamino-benzylidene)-3,4-dimethyl-1,5-dihydro-pyrrol-2-one 

Relevant articles and documents

Large scale, efficient synthesis of 9-unsubstituted dipyrrinone

9-Unsubstituted dipyrrinone 8, the useful precursor for the synthesis of biliverdins, bilirubins, and other bile pigments, was synthesized in large scale and high yield starting from acetaldehyde and nitroethane in eight steps with overall yield 10%. The key intermediate 3,4-dimethyl-2-ethoxycarbonylpyrrole 3 was synthesized via Zard-Barton's method in high yield.

New open-chain tetrapyrroles as chromophores in the plant photoreceptor phytochrome

A series of six open-chain tetrapyrroles has been synthesized and used as chromophores for the plant photoreceptor protein phytochrome. The novel chromophores vary in the size of substituents 17 and 18 at ring D. This ring undergoes maximal conformational change upon light excitation (Z → E photoisomerization of the 15,16-double bond). Instead of methyl and vinyl substituents (positions 17, 18) as present in the native chromophore phytochromobilin, dimethyl, methyl and isopropyl, methyl and tert-butyl, ethyl and methyl, vinyl and methyl, and isopropyl and methyl substituents have been generated. All novel chromophores assemble with the apoprotein. The obtained chromoproteins show hypsochromic shifts of the absorbance maxima by 10 nm maximally, compared to the native pigment, except for the 17-isopropyl-18- methyl-substituted compound which showed a 100 nm hypsochromic shift of selectively the Pr form. The assembly kinetics were slowed down in correlation to the increasing size of the substituents, with stronger effects for modified substituents at position 17. The thermal stability of the photoinduced Pfr form for the 18-isopropyl and the 18-tert butyl substituents was even greater than that of the native pigments. Those chromophores carrying substituents at position 17 larger than the methyl group (ethyl and isopropyl) showed a very low stability of the respective P fr forms. Time-resolved detection of the Pfr to Pfr conversion (laser-induced flash photolysis) revealed a slower formation of the Pfr form for those chromophores carrying larger substituents at position 18, whereas the rise and decay kinetics of the early intermediates are only moderately changed. Introduction of larger substituents at position 17 (ethyl, vinyl, and isopropyl) causes drastic changes in the kinetics; in particular the formation of the first thermally stable intermediate, I 700, is significantly slowed, making a detection of its rise possible.

Regiocontrolled synthesis of pyrrole-2-carboxaldehydes and 3-pyrrolin-2-ones from pyrrole Weinreb amides

A regiocontrolled synthesis of 3,4-disubstituted pyrrole-2-carboxaldehydes was completed in two steps from acyclic starting materials. A Barton-Zard pyrrole synthesis between N-methoxy-N-methyl-2-isocyanoacetamide and α-nitroalkenes or β-nitroacetates provided N-methoxy-N-methyl pyrrole-2-carboxamides (pyrrole Weinreb amides), which were converted into the corresponding pyrrole-2-carboxaldehydes by treatment with lithium aluminum hydride. A regioselective oxidation of the pyrrole-2-carboxaldehydes gave the corresponding 3,4-disubstituted 3-pyrrolin-2-ones.