Production Method 1

402-51-7

625852-40-6

869318-90-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 12 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Copper(I)-catalyzed site-selective C(sp3)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T

Jin, Jianwen; et al, Nature Communications, 2021, 12(1),

Production Method 2

1245806-42-1

869318-90-1

Reaction Conditions

1.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane

Reference

Regioselective introduction of vinyl trifluoromethylthioether to remote unactivated C(sp3)-H bonds via radical translocation cascade

Wu, Shuo; et al, Science China: Chemistry, 2019, 62(11), 1507-1511

Production Method 3

455-19-6

4548-78-1

869318-90-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 2 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  overnight, 0 °C; 0 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Radical heteroarylation of unactivated remote C(sp3)-H bonds via intramolecular heteroaryl migration

Cao, Zhu; et al, Organic Chemistry Frontiers, 2021, 8(22), 6395-6399

Production Method 4

455-24-3

6638-79-5

869318-90-1

Reaction Conditions

1.1 Reagents: Triethylamine Solvents: Dichloromethane ;  0 °C; 0 °C → rt; 3 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ;  rt
2.1 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Relay C-H Functionalization Enables De Novo Synthesis of Pyridines and Pyridones

Liu, Qing-Peng; et al, ACS Catalysis, 2023, 13(9), 5795-5807

Production Method 5

646-07-1

6638-79-5

869318-90-1

Reaction Conditions

1.1 Reagents: Triethylamine ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  12 h, rt
1.2 Reagents: Water
2.1 Solvents: Tetrahydrofuran ;  0 °C; 12 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water

Reference

Copper(I)-catalyzed site-selective C(sp3)-H bond chlorination of ketones, (E)-enones and alkylbenzenes by dichloramine-T

Jin, Jianwen; et al, Nature Communications, 2021, 12(1),

Production Method 6

4548-78-1

116332-61-7

869318-90-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Relay C-H Functionalization Enables De Novo Synthesis of Pyridines and Pyridones

Liu, Qing-Peng; et al, ACS Catalysis, 2023, 13(9), 5795-5807

Production Method 7

4548-78-1

116332-61-7

869318-90-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Iminyl radical-triggered relay annulation for the construction of bridged aza-tetracycles bearing four contiguous stereogenic centers

Jiang, Kun; et al, Chemical Science, 2022, 13(24), 7283-7288

Production Method 8

1245806-42-1

869318-90-1

Reaction Conditions

1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  overnight, 0 °C; 0 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water

Reference

Radical heteroarylation of unactivated remote C(sp3)-H bonds via intramolecular heteroaryl migration

Cao, Zhu; et al, Organic Chemistry Frontiers, 2021, 8(22), 6395-6399

Production Method 9

1245806-42-1

869318-90-1

Reaction Conditions

1.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane

Reference

Remote C(sp3)-H vinylation via radical-mediated consecutive fission of C-H and C-C bonds

Niu, Tao; et al, Organic Chemistry Frontiers, 2020, 7(19), 2981-2985

Production Method 10

455-19-6

4548-78-1

869318-90-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  1 - 2 h, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt
1.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  rt

Reference

Regioselective Sulfonylvinylation of the Unactivated C(sp3)-H Bond via a C-Centered Radical-Mediated Hydrogen Atom Transfer (HAT) Process

Yang, Shan; et al, Organic Letters, 2019, 21(12), 4837-4841

Production Method 11

455-19-6

4548-78-1

869318-90-1

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  0 °C; 1 - 2 h, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Pyridinium chlorochromate Solvents: Dichloromethane

Reference

Remote C(sp3)-H vinylation via radical-mediated consecutive fission of C-H and C-C bonds

Niu, Tao; et al, Organic Chemistry Frontiers, 2020, 7(19), 2981-2985

Production Method 12

455-24-3

6638-79-5

869318-90-1

Reaction Conditions

1.1 Reagents: 1,1′-Carbonyldiimidazole Solvents: Dichloromethane ;  1 h, rt
1.2 rt; 48 h, rt
1.3 Reagents: Sodium bicarbonate Solvents: Water
2.1 Solvents: Tetrahydrofuran ;  0 °C; 0 °C → rt; 12 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water

Reference

Iminyl radical-triggered relay annulation for the construction of bridged aza-tetracycles bearing four contiguous stereogenic centers

Jiang, Kun; et al, Chemical Science, 2022, 13(24), 7283-7288

4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one Raw materials

• 4-(Trifluoromethyl)benzoic acid
• 4-Methyl-1-(4-(trifluoromethyl)phenyl)pentan-1-ol
• 4-(Trifluoromethyl)benzaldehyde
• 4-Methylpentanoic acid
• Bromo[4-(trifluoromethyl)phenyl]magnesium
• N,O-Dimethylhydroxylamine hydrochloride
• N-methoxy-N,4-dimethylpentanamide
• Magnesium, bromo(3-methylbutyl)-
• N-Methoxy-N-methyl-4-(trifluoromethyl)benzamide

4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one Preparation Products

• 4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one (869318-90-1)

• 1. An Appraisal of pH triggered Bacitracin drug release, through composite hydrogel systems
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• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Ketones
• Solvents and Organic Chemicals Organic Compounds Organic oxygen compounds Organooxygen compounds Carbonyl compounds Ketones

Research Briefing on 4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one (CAS: 869318-90-1) in Chemical Biology and Pharmaceutical Applications

4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one (CAS: 869318-90-1) is a fluorinated aromatic ketone compound that has garnered significant attention in recent years due to its versatile applications in chemical biology and pharmaceutical research. This compound, characterized by its trifluoromethylphenyl moiety, serves as a key intermediate in the synthesis of various bioactive molecules, including potential drug candidates. The unique electronic and steric properties imparted by the trifluoromethyl group make this compound particularly valuable in medicinal chemistry, where it is often employed to modulate the pharmacokinetic and pharmacodynamic profiles of lead compounds.

Recent studies have explored the synthetic utility of 4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one in the development of novel therapeutic agents. A 2023 publication in the Journal of Medicinal Chemistry demonstrated its use as a precursor in the synthesis of small-molecule inhibitors targeting protein-protein interactions (PPIs) involved in cancer progression. The researchers highlighted the compound's role in facilitating the introduction of the trifluoromethyl group, which enhanced the binding affinity and metabolic stability of the resulting inhibitors. This study underscores the growing importance of fluorinated building blocks in drug discovery.

In addition to its applications in oncology, 4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one has shown promise in central nervous system (CNS) drug development. A 2022 study published in ACS Chemical Neuroscience reported its incorporation into novel neuroprotective agents designed to mitigate oxidative stress in neurodegenerative diseases. The trifluoromethyl group was found to improve blood-brain barrier permeability while maintaining favorable safety profiles. These findings suggest that this compound could play a pivotal role in addressing the challenges associated with CNS drug delivery.

The compound's mechanism of action and structure-activity relationships (SAR) have been the subject of ongoing investigation. Computational chemistry approaches, including molecular docking and quantum mechanical calculations, have been employed to elucidate how the trifluoromethyl group influences molecular recognition processes. These studies have provided valuable insights for rational drug design, particularly in optimizing ligand-receptor interactions. The latest research indicates that the steric and electronic effects of the trifluoromethyl group can significantly alter binding kinetics and selectivity.

From a synthetic chemistry perspective, recent advancements have focused on developing more efficient and sustainable routes to produce 4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one. A 2023 Green Chemistry publication described a catalytic system that enables the direct trifluoromethylation of aromatic compounds under mild conditions, offering improved yields and reduced environmental impact compared to traditional methods. These methodological innovations are expected to facilitate broader adoption of this valuable building block in pharmaceutical research and development.

Looking forward, the potential applications of 4-Methyl-1-[4-(trifluoromethyl)phenyl]pentan-1-one appear to be expanding beyond small-molecule therapeutics. Emerging research suggests its utility in the development of chemical probes for biological target identification and validation, as well as in the synthesis of advanced materials for drug delivery systems. The compound's versatility and the growing demand for fluorinated pharmaceuticals position it as a significant focus area for future research in chemical biology and medicinal chemistry.

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