Production Method 1

2935-44-6

822-64-0

930-87-0

625-84-3

Reaction Conditions

1.1 Reagents: Ammonia Catalysts: (OC-6-52)-[4,5-Bis[[bis(1-methylethyl)phosphino-κP]methyl]acridine-κN]carbonylch… Solvents: Toluene ;  24 h, 7 atm, 150 °C

Reference

Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium

Daw, Prosenjit; Ben-David, Yehoshoa; Milstein, David, Journal of the American Chemical Society, 2018, 140(38), 11931-11934

3,4-dihydro-2,5-dimethyl-2H-Pyrrole Raw materials

• Hexane-2,5-diol

3,4-dihydro-2,5-dimethyl-2H-Pyrrole Preparation Products

• 1,2,5-Trimethylpyrrole (930-87-0)
• 3,4-dihydro-2,5-dimethyl-2H-Pyrrole (822-64-0)
• 2,5-Dimethyl-1H-pyrrole (625-84-3)

• 1. Evidence of CO2 molecule acting as an electron acceptor on a nanoporous metal–organic-framework MIL-53 or Cr3+(OH)(O2C–C6H4–CO2)?
  Alexandre Vimont,Arnaud Travert,Philippe Bazin,Jean-Claude Lavalley,Marco Daturi,Christian Serre,Gérard Férey,Sandrine Bourrelly,Philip L. Llewellyn Chem. Commun., 2007, 3291-3293
• 2. Excimer–monomer switch: a reaction-based approach for selective detection of fluoride?
  Qiao Song,Angela Bamesberger,Lingyun Yang,Haley Houtwed,Haishi Cao Analyst, 2014,139, 3588-3592
• 3. Establishing empirical design rules of nucleic acid templates for the synthesis of silver nanoclusters with tunable photoluminescence and functionalities towards targeted bioimaging applications?
  Jason Y. C. Lim,Yong Yu,Guorui Jin,Kai Li,Yi Lu,Jianping Xie Nanoscale Adv., 2020,2, 3921-3932
• 4. Evolution of dealloying induced strain in nanoporous gold crystals?
  Ross Harder,David C. Dunand,Ian McNulty Nanoscale, 2017,9, 5686-5693
• 5. Evidence that the availability of an allylic hydrogen governs the regioselectivity of the Wacker oxidation
  Matthew J. Gaunt,Jinquan Yu,Jonathan B. Spencer Chem. Commun., 2001, 1844-1845

• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolines Pyrrolines
• Solvents and Organic Chemicals Organic Compounds Organoheterocyclic compounds Pyrrolines

3,4-Dihydro-2,5-Dimethyl-2H-Pyrrole: An Overview of a Versatile Heterocyclic Compound

3,4-Dihydro-2,5-dimethyl-2H-pyrrole (CAS No. 822-64-0) is a heterocyclic compound that has garnered significant attention in the fields of organic chemistry and medicinal chemistry due to its unique structural properties and potential applications. This compound belongs to the class of pyrroles, which are five-membered heterocyclic rings containing four carbon atoms and one nitrogen atom. The presence of two methyl groups at the 2 and 5 positions, along with the dihydro configuration, imparts distinct chemical and biological characteristics to this molecule.

The synthesis of 3,4-dihydro-2,5-dimethyl-2H-pyrrole has been extensively studied, with various methods reported in the literature. One common approach involves the condensation of an appropriate ketone or aldehyde with a nitrogen-containing reagent, followed by cyclization and reduction steps. Recent advancements in catalytic methods have further simplified the synthesis process, making it more accessible for large-scale production and industrial applications.

In terms of its physical properties, 3,4-dihydro-2,5-dimethyl-2H-pyrrole is typically a colorless liquid with a characteristic odor. It is soluble in common organic solvents such as ethanol, methanol, and dichloromethane but has limited solubility in water. These properties make it suitable for use in a variety of chemical reactions and formulations.

The chemical reactivity of 3,4-dihydro-2,5-dimethyl-2H-pyrrole is influenced by its heterocyclic structure and the presence of the methyl groups. The nitrogen atom in the pyrrole ring can act as a nucleophile or a base, facilitating various reactions such as electrophilic substitution, nucleophilic addition, and Michael addition. The dihydro configuration adds further reactivity by allowing for redox reactions and hydrogenation processes.

In the context of medicinal chemistry, 3,4-dihydro-2,5-dimethyl-2H-pyrrole has shown promise as a scaffold for the development of bioactive compounds. Recent studies have explored its potential as an inhibitor of specific enzymes involved in disease pathways. For instance, researchers have synthesized derivatives of this compound that exhibit potent inhibitory activity against enzymes such as cyclooxygenase (COX) and lipoxygenase (LOX), which are key targets in inflammation and cancer therapy.

Beyond its direct biological activity, 3,4-dihydro-2,5-dimethyl-2H-pyrrole serves as a valuable building block for the synthesis of more complex molecules. Its versatile reactivity allows chemists to introduce various functional groups and substituents, leading to a wide range of derivatives with diverse biological activities. This makes it an attractive starting material for drug discovery programs targeting multiple therapeutic areas.

The environmental impact of 3,4-dihydro-2,5-dimethyl-2H-pyrrole is also an important consideration. While it is not classified as a hazardous substance under current regulations, proper handling and disposal practices should be followed to minimize any potential environmental risks. Green chemistry principles are increasingly being applied to the synthesis and use of this compound to ensure sustainable practices.

In conclusion, 3,4-dihydro-2,5-dimethyl-2H-pyrrole (CAS No. 822-64-0) is a versatile heterocyclic compound with significant potential in both academic research and industrial applications. Its unique structural features and chemical reactivity make it an important molecule for the development of new materials and bioactive compounds. Ongoing research continues to uncover new applications and optimize synthetic methods for this intriguing compound.

• 213979-95-4(5-Nonanamine, N-(1-butylpentylidene)-)
• 61772-94-9(2H-Pyrrole, 5-ethyl-3,4-dihydro-2-pentyl-)
• 61772-93-8(2H-Pyrrole, 2-ethyl-5-heptyl-3,4-dihydro-)
• 83688-87-3(2H-Pyrrole, 2-butyl-5-heptyl-3,4-dihydro-)
• 59785-53-4(2H-Pyrrole, 5-ethyl-3,4-dihydro-2-methyl-)
• 61772-95-0(2H-Pyrrole, 2-ethyl-3,4-dihydro-5-pentyl-)
• 213979-94-3(3-Nonanamine, N-(1-ethylheptylidene)-)
• 6114-69-8(Cyclohexanamine, N-cycloheptylidene-)
• 106119-01-1(2H-Pyrrole, 2-butyl-3,4-dihydro-5-methyl-)
• 88226-76-0(Cyclohexanamine, N-(1-ethylbutylidene)-, (E)-)