Production Method 1

403-45-2

84331-14-6

Reaction Conditions

1.1 Reagents: 1-Hydroxybenzotriazole ,  Diisopropylethylamine ,  1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride Solvents: Dichloromethane ;  10 min, 0 °C
1.2 Reagents: N,O-Dimethylhydroxylamine hydrochloride ;  16 h, rt
1.3 Solvents: Diethyl ether ,  Tetrahydrofuran ;  20 min, 0 °C; 3 h, 0 °C
1.4 Reagents: Ammonium chloride Solvents: Water ;  0 °C

Reference

Modular Synthesis of Alkenyl Sulfamates and β-Ketosulfonamides via Sulfur(VI) Fluoride Exchange (SuFEx) Click Chemistry and Photomediated 1,3-Rearrangement

Sousa e Silva, Felipe Cesar; et al, Organic Letters, 2021, 23(13), 5271-5276

Production Method 2

84331-14-6

Reaction Conditions

1.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  4 h, 60 °C

Reference

A method for the nucleophilic fluorination of 4-dimethylaminopyridine (DMAP) pyridinium salts

Cressy, Derek; et al, Results in Chemistry, 2023, 5,

Production Method 3

55676-22-7

1122-58-3

84331-14-6

Reaction Conditions

1.1 Solvents: Tetrahydrofuran ;  overnight, 60 °C
2.1 Reagents: Cesium fluoride Solvents: Dimethylformamide ;  4 h, 60 °C

Reference

A method for the nucleophilic fluorination of 4-dimethylaminopyridine (DMAP) pyridinium salts

Cressy, Derek; et al, Results in Chemistry, 2023, 5,

Production Method 4

1034467-37-2

84331-14-6

Reaction Conditions

1.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  2 h, rt
1.2 Reagents: Sodium bicarbonate ,  Sodium thiosulfate Solvents: Water ;  5 min, rt

Reference

Asymmetric Biocatalytic Synthesis of Fluorinated Pyridines through Transesterification or Transamination: Computational Insights into the Reactivity of Transaminases

Lopez-Iglesias, Maria; et al, Advanced Synthesis & Catalysis, 2017, 359(2), 279-291

Production Method 5

55676-22-7

84331-14-6

Reaction Conditions

1.1 Reagents: Cesium fluoride Catalysts: Tetramethylammonium chloride ,  18-Crown-6 Solvents: Acetonitrile ;  16 h, rt → 60 °C

Reference

Nucleophilic Fluorination of Heteroaryl Chlorides and Aryl Triflates Enabled by Cooperative Catalysis

Hong, Cynthia M. ; et al, Journal of Organic Chemistry, 2021, 86(5), 3999-4006

Production Method 6

766-11-0

84331-14-6

Reaction Conditions

1.1 Reagents: Butyllithium Solvents: Diethyl ether ,  Hexane ;  -78 °C; 30 min, -78 °C
1.2 Solvents: Diethyl ether ;  -78 °C; 1.5 h, -78 °C
1.3 Solvents: Water ;  -78 °C → rt
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 8, rt
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ;  2 h, rt
2.2 Reagents: Sodium bicarbonate ,  Sodium thiosulfate Solvents: Water ;  5 min, rt

Reference

Asymmetric Biocatalytic Synthesis of Fluorinated Pyridines through Transesterification or Transamination: Computational Insights into the Reactivity of Transaminases

Lopez-Iglesias, Maria; et al, Advanced Synthesis & Catalysis, 2017, 359(2), 279-291

1-(6-Fluoropyridin-3-yl)ethanone Raw materials

• 6-fluoropyridine-3-carboxylic acid
• 1-(6-Fluoropyridin-3-yl)ethan-1-ol
• 3-Acetyl-6-chloropyridine
• 4-Dimethylaminopyridine
• 5-Bromo-2-fluoropyridine

1-(6-Fluoropyridin-3-yl)ethanone Preparation Products

• 1-(6-Fluoropyridin-3-yl)ethanone (84331-14-6)

• 1. An artificial photosynthetic system for photoaccumulation of two electrons on a fused dipyridophenazine (dppz)–pyridoquinolinone ligand?
  Philipp Traber,Stephan Kupfer,Stefanie Gr?fe,Isabelle Baussanne,Martine Demeunynck,Jean-Marie Mouesca,Serge Gambarelli,Vincent Artero,Murielle Chavarot-Kerlidou Chem. Sci., 2018,9, 4152-4159
• 2. An ATP-selective, lanthanide complex luminescent probe?
  Xiao Liu,Jun Xu,Yinyun Lv,Wenyu Wu,Weisheng Liu,Yu Tang Dalton Trans., 2013,42, 9840-9846
• 3. An amphoteric reactivity of a mixed-valent bis(μ-oxo)dimanganese(iii,iv) complex acting as an electrophile and a nucleophile?
  Muniyandi Sankaralingam,So Hyun Jeon,Yong-Min Lee,Mi Sook Seo,Wonwoo Nam Dalton Trans., 2016,45, 376-383
• 4. An integrated droplet-digital microfluidic system for on-demand droplet creation, mixing, incubation, and sorting?
  Lab Chip, 2019,19, 524-535
• 5. An ionic liquid-based synergistic extraction strategy for rare earths?
  Yingbo Li,Nada Mehio,Huizhou Liu,Sheng Dai Green Chem., 2015,17, 2981-2993

• 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
• Solvents and Organic Chemicals Organic Compounds

Introduction to 1-(6-Fluoropyridin-3-yl)ethanone (CAS No. 84331-14-6)

1-(6-Fluoropyridin-3-yl)ethanone, also known by its CAS number 84331-14-6, is a versatile organic compound that has garnered significant attention in the fields of medicinal chemistry and pharmaceutical research. This compound is characterized by its unique structural features, which include a fluorinated pyridine ring and an acetone moiety. These features contribute to its potential applications in the development of novel therapeutic agents and as a valuable intermediate in synthetic chemistry.

The chemical structure of 1-(6-Fluoropyridin-3-yl)ethanone consists of a 6-fluoropyridine ring attached to an acetone group. The presence of the fluorine atom imparts unique electronic and steric properties to the molecule, making it an attractive candidate for various chemical transformations. Fluorinated compounds are known for their enhanced metabolic stability and improved pharmacokinetic profiles, which are crucial factors in drug design.

In recent years, 1-(6-Fluoropyridin-3-yl)ethanone has been extensively studied for its potential as a building block in the synthesis of bioactive molecules. One notable application is in the development of inhibitors for various enzymes and receptors. For instance, researchers have explored its use in the synthesis of inhibitors for kinases, which are key targets in cancer therapy. The ability to modulate kinase activity through small molecule inhibitors is a promising strategy for developing targeted cancer therapies.

Beyond its role in drug discovery, 1-(6-Fluoropyridin-3-yl)ethanone has also found applications in the synthesis of fluorescent probes and imaging agents. Fluorescent probes are essential tools in biological research, enabling the visualization and quantification of cellular processes. The fluorinated pyridine ring in 1-(6-Fluoropyridin-3-yl)ethanone can be modified to enhance its fluorescence properties, making it a valuable starting material for the development of new imaging agents.

The synthetic accessibility of 1-(6-Fluoropyridin-3-yl)ethanone has been well-documented in the literature. Several efficient synthetic routes have been developed to prepare this compound, including metal-catalyzed cross-coupling reactions and electrophilic aromatic substitution reactions. These methods allow for the scalable production of 1-(6-Fluoropyridin-3-yl)ethanone, facilitating its use in both academic and industrial settings.

In addition to its synthetic utility, the physical and chemical properties of 1-(6-Fluoropyridin-3-yl)ethanone have been thoroughly characterized. It is a colorless liquid with a boiling point around 120°C at atmospheric pressure. The compound exhibits good solubility in common organic solvents such as dichloromethane, ethanol, and dimethyl sulfoxide (DMSO). These properties make it easy to handle and process in laboratory settings.

The safety profile of 1-(6-Fluoropyridin-3-yl)ethanone has also been evaluated. While it is not classified as a hazardous substance, standard laboratory safety protocols should be followed when handling this compound. Proper personal protective equipment (PPE), such as gloves and safety goggles, should be worn to minimize exposure risks.

In conclusion, 1-(6-Fluoropyridin-3-yl)ethanone (CAS No. 84331-14-6) is a multifaceted compound with significant potential in medicinal chemistry and pharmaceutical research. Its unique structural features and synthetic accessibility make it an invaluable tool for the development of novel therapeutic agents and imaging probes. As research continues to advance, it is likely that new applications for this compound will be discovered, further solidifying its importance in the scientific community.

• 79574-70-2(3-Acetyl-2-fluoropyridine)
• 871325-13-2(5-ethyl-2-fluoropyridine)
• 84331-15-7(Ethanone, 2-bromo-1-(6-fluoro-3-pyridinyl)-)
• 111887-72-0(1-(2-Fluoropyridin-4-yl)ethanone)
• 885132-93-4(1-Propanone,1-(2,6-difluoro-3-pyridinyl)-)
• 136592-25-1(2-chloro-1-(6-fluoropyridin-3-yl)ethan-1-one)
• 677728-92-6(6-fluoropyridine-3-carbaldehyde)
• 871325-14-3(5-ethyl-2-fluoro-3-Pyridinecarboxaldehyde)
• 920036-27-7(1-(2,6-Difluoropyridin-3-yl)ethanone)
• 145005-30-7(Ethanone,2-fluoro-1-(2-fluoro-3-pyridinyl)-)