208110-81-0

Basic information

• Product Name: 2-Fluoro-6-formylpyridine
• Synonyms: 2-FLUORO-6-FORMYLPYRIDINE;CHEMPACIFIC 38134;6-Fluoropyridine-2-carboxalehyde;6-FLUORO-PYRIDINE-2-CARBALDEHYDE;6-Fluoropyridine-2-carboxaldehyde;2-Pyridinecarboxaldehyde,6-fluoro-(9CI);6-Fluoropicolinaldehyde;6-FLUOROPICOLINALDEHYDE,98.5%
• CAS NO: 208110-81-0
• Molecular Formula: C₆H₄FNO
• Molecular Weight: 125.1
• Product Categories: PYRIDINE
• Mol File: 208110-81-0.mol
• Article Data: 8

Chemical Properties

• Boiling Point: 192.378 °C at 760 mmHg
• Flash Point: 70.148 °C
• Appearance: /
• Density: 1.27 g/cm³
• Vapor Pressure: 0.0028mmHg at 25°C
• Refractive Index: 1.513
• Storage Temp.: Store Cold
• PKA: 0.80±0.10(Predicted)
• CAS DataBase Reference: 2-Fluoro-6-formylpyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-6-formylpyridine(208110-81-0)
• EPA Substance Registry System: 2-Fluoro-6-formylpyridine(208110-81-0)

Safety Data

• Hazard Codes: Xi,F
• Statements: 10-36/37/38
• Safety Statements: 16-26-36
• RIDADR: UN2811
• Hazardous Substances Data: 208110-81-0(Hazardous Substances Data)

Usage

Description

2-Fluoro-6-formylpyridine is a heterocyclic organic compound characterized by the presence of a fluorine atom and an aldehyde group attached to a pyridine ring. This unique structure endows it with specific chemical properties that make it a valuable intermediate in the synthesis of various pharmaceutical compounds.

Uses

Used in Pharmaceutical Industry:
2-Fluoro-6-formylpyridine is used as a key intermediate in the synthesis of fluoroheterocyclic aldoximes, which are therapeutic agents for the treatment of anti-cholinesterase poisoning. Its incorporation into these compounds enhances their pharmacological properties, making them more effective in counteracting the toxic effects of anti-cholinesterase agents.

InChI:InChI=1/C3H5FINO/c1-6-3(7)2(4)5/h2H,1H3,(H,6,7)

Synthetic route

methyl 6-fluoropyridine-2-carboxylate (455-71-0) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
With diisobutylaluminium hydride In dichloromethane at -55℃; for 3h; Inert atmosphere;	84%

6-fluoropyridine-2-carbonyl chloride (64197-03-1) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
With Pd-BaSO4; hydrogen Rosenmund reduction;	68%

2-fluoro-6-(dibromomethyl)pyridine (1243694-61-2) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
With silver nitrate In water; acetonitrile at 20℃; for 3h;	60%

2-fluoro-6-methylpyridine (407-22-7) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
With sodium periodate; tert-Butoxybis(dimethylamino)methane 1.) 140 deg C, 24 h, 2.) H2O, 25 deg C, p = 80 mbar; Yield given; Multistep reaction;
With sodium periodate; n-butyllithium; diisopropylamine In tetrahydrofuran; water
Multi-step reaction with 3 steps 1: potassium permanganate / water / Reflux 2: thionyl chloride 3: Pd-BaSO4; hydrogen View Scheme
With sodium periodate; n-butyllithium; diisopropylamine In tetrahydrofuran; water
Stage #1: 2-fluoro-6-methylpyridine With n-butyllithium; diisopropylamine; N,N-dimethyl-formamide In tetrahydrofuran; hexanes at -78 - 0℃; for 1.75h; Stage #2: With sodium periodate In tetrahydrofuran; hexanes; water at 0 - 20℃; for 25h;

2-fluoro-6-methylpyridine (407-22-7) + tert-Butoxybis(dimethylamino)methane (5815-08-7) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
With sodium periodate In tetrahydrofuran
With sodium periodate In water

2-Amino-6-methylpyridine (1824-81-3) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
Multi-step reaction with 4 steps 1: tetrafluoroboric acid; sodium nitrite / water 2: potassium permanganate / water / Reflux 3: thionyl chloride 4: Pd-BaSO4; hydrogen View Scheme

6-fluoropyridine-2-carboxylic acid (402-69-7) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: thionyl chloride 2: Pd-BaSO4; hydrogen View Scheme

methyl pyridine-2-carboxylate (2459-07-6) → 2-Fluoropyridine-6-carboxaldehyde (208110-81-0)

Conditions	Yield
Multi-step reaction with 2 steps 1: silver(II) fluoride / acetonitrile / 20 °C / Inert atmosphere; Autoclave 2: diisobutylaluminium hydride / dichloromethane / 3 h / -55 °C / Inert atmosphere View Scheme

4-amino-N,N-dimethylaniline (99-98-9) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 4-(((6-fluoropyridin-2-yl)methylene)amino)-N,N-dimethylaniline

Conditions	Yield
With sodium sulfate In tetrahydrofuran at 20℃; for 24h; Inert atmosphere; Schlenk technique;	100%

2,6-diethylaniline (579-66-8) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → C16H17FN2

Conditions	Yield
In ethanol at 80℃; for 12h; Inert atmosphere;	97%

2,6-diisopropylbenzenamine (24544-04-5) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → C18H21FN2

Conditions	Yield
In ethanol at 80℃; for 12h; Inert atmosphere;	96%

2-isopropylaniline (643-28-7) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → C15H15FN2

Conditions	Yield
In ethanol at 80℃; for 12h; Inert atmosphere;	90%

malononitrile (109-77-3) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → C9H6FN3 (1284237-48-4)

Conditions	Yield
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate; piperdinium acetate In toluene at 105℃; for 3h; Inert atmosphere;	86%

ethylene glycol (107-21-1) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 2-(1,3-dioxolan-2-yl)-6-fluoropyridin (208111-44-8)

Conditions	Yield
With toluene-4-sulfonic acid In benzene for 18h; Heating;	80%

2,2-diethoxy-ethanamine (645-36-3) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → (2,2-diethoxyethyl)((6-fluoropyridin-2-yl)methyl)amine

Conditions	Yield
Stage #1: 2,2-diethoxy-ethanamine; 2-Fluoropyridine-6-carboxaldehyde With acetic acid In tetrahydrofuran at 20℃; for 0.416667h; Stage #2: With sodium tris(acetoxy)borohydride at 20℃; for 1.16667h;	74%

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 2-fluoropyridine-6-aldoxime (1319649-66-5)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In water for 0.333333h; Reflux;	71%

1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → C16H22FN3O2

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃; for 18h;	53%

1-(tert-butoxycarbonyl)-4-aminopiperidine (87120-72-7) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → (E)-tert-butyl 4-(((6-fluoropyridin-2-yl)methylene)amino)piperidine-1-carboxylate

Conditions	Yield
With magnesium sulfate In dichloromethane at 20℃;	53%

2-amino-4,6-dimethoxybenzamide (63920-73-0) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 2-(6-fluoropyridin-2-yl)-5,7-dimethoxyquinazolin-4(3H)-one (1610379-38-8)

Conditions	Yield
With toluene-4-sulfonic acid; sodium hydrogensulfite In N,N-dimethyl acetamide at 120℃; for 20h;	49%

4-Aminomethylpiperidine (7144-05-0) + 3,4-dichlorobenzoyl chloride (3024-72-4) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → (3,4-Dichloro-phenyl)-(4-{[(6-fluoro-pyridine-2-ylmethyl)-amino]methyl}-piperidine-1-yl)-methanone (208109-29-9)

Conditions	Yield
With Potassium borohydride; triethylamine In tetrahydrofuran; methanol; water; benzene	40%

4-Aminomethylpiperidine (7144-05-0) + 2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → [1-(6-Fluoro-pyridin-2-yl)-meth-(E)-ylidene]-piperidin-4-ylmethyl-amine (1025812-07-0)

Conditions	Yield
In toluene for 2h; Heating;

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 6-(methylthio)pyridine-2-carboxaldehyde (217657-76-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 73 percent / dimethylformamide / 18 h / 100 °C 3: 45 percent / HCO2H / H2O / 65 °C View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 6-(methylsulfinyl)pyridine-2-carboxaldehyde (217657-77-7)

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 73 percent / dimethylformamide / 18 h / 100 °C 3: 67 percent / NaIO4 / methanol; H2O / 18 h / Ambient temperature 4: 60 percent / HCO2H / H2O / 65 °C View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 2-(1H-pyrazol-1-yl)pyridine-6-carbaldehyde (217657-66-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 1.) NaH / 1.) DMF, 2 h, 2.) DMF, 80 deg C, 3 h 3: 79 percent / CuSO4*5H2O, formic acid / H2O / 5 h / 65 °C View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 6-n-butoxypyridine-2-carboxaldehyde (217657-79-9)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 90 percent / Na / 18 h / 100 °C 3: HCO2H / H2O / 65 °C View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 2-(1,3-dioxolan-2-yl)-6-(methylthio)pyridine (217657-74-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 73 percent / dimethylformamide / 18 h / 100 °C View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 6-(methylsulfinyl)-2-(1,3-dioxolan-2-yl)pyridine (217657-75-5)

Conditions	Yield
Multi-step reaction with 3 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 73 percent / dimethylformamide / 18 h / 100 °C 3: 67 percent / NaIO4 / methanol; H2O / 18 h / Ambient temperature View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 6-pyrazolo-2-(1,3-dioxolan-2-yl)pyridine (217657-64-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 1.) NaH / 1.) DMF, 2 h, 2.) DMF, 80 deg C, 3 h View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → 6-n-butoxy-2-(1,3-dioxolan-2-yl)pyridine (217657-78-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 90 percent / Na / 18 h / 100 °C View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → [1-(6-Methylsulfanyl-pyridin-2-yl)-meth-(E)-ylidene]-piperidin-4-ylmethyl-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 73 percent / dimethylformamide / 18 h / 100 °C 3: 45 percent / HCO2H / H2O / 65 °C 4: toluene / 2 h / Heating View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → [1-(6-Methanesulfinyl-pyridin-2-yl)-meth-(E)-ylidene]-piperidin-4-ylmethyl-amine

Conditions	Yield
Multi-step reaction with 5 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 73 percent / dimethylformamide / 18 h / 100 °C 3: 67 percent / NaIO4 / methanol; H2O / 18 h / Ambient temperature 4: 60 percent / HCO2H / H2O / 65 °C 5: toluene / 2 h / Heating View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → [2-(4-methoxy-phenyl)-ethyl]-(6-pyrazol-1-yl-pyridin-2-ylmethyl)-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 1.) NaH / 1.) DMF, 2 h, 2.) DMF, 80 deg C, 3 h 3: 79 percent / CuSO4*5H2O, formic acid / H2O / 5 h / 65 °C 4: NaBH(OAc)3 / 1,2-dichloro-ethane / 24 h / Ambient temperature View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → Piperidin-4-ylmethyl-[1-(6-pyrazol-1-yl-pyridin-2-yl)-meth-(E)-ylidene]-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 1.) NaH / 1.) DMF, 2 h, 2.) DMF, 80 deg C, 3 h 3: 79 percent / CuSO4*5H2O, formic acid / H2O / 5 h / 65 °C 4: toluene / 2 h / Heating View Scheme

2-Fluoropyridine-6-carboxaldehyde (208110-81-0) → [1-(6-Butoxy-pyridin-2-yl)-meth-(E)-ylidene]-piperidin-4-ylmethyl-amine

Conditions	Yield
Multi-step reaction with 4 steps 1: 80 percent / PTSA*H2O / benzene / 18 h / Heating 2: 90 percent / Na / 18 h / 100 °C 3: HCO2H / H2O / 65 °C 4: toluene / 2 h / Heating View Scheme

Upstream product

• 407-22-7 2-fluoro-6-methylpyridine 
• 5815-08-7 tert-Butoxybis(dimethylamino)methane 
• 1243694-61-2 2-fluoro-6-(dibromomethyl)pyridine 
• 64197-03-1 6-fluoropyridine-2-carbonyl chloride 
• 1824-81-3 2-Amino-6-methylpyridine 
• 402-69-7 6-fluoropyridine-2-carboxylic acid 
• 2459-07-6 methyl pyridine-2-carboxylate 
• 455-71-0 methyl 6-fluoropyridine-2-carboxylate 

Downstream Products

• 217657-76-6 6-(methylthio)pyridine-2-carboxaldehyde 
• 208109-29-9 (3,4-Dichloro-phenyl)-(4-{[(6-fluoro-pyridine-2-ylmethyl)-amino]methyl}-piperidine-1-yl)-methanone 

Relevant articles and documents

Separation of geometric isomers of a dicopper complex by using a 19F-labeled ligand: Dynamics, structures, and DFT calculations

Introducing a fluorine group on two pyridines of the HLCH3 ligand (2,6-bis[(bis(2-pyridylmethyl)amino)methyl]-4-methylphenol) allows the separation of two geometric isomers after complexation by two copper(II) ions. Methods for isolating the is

Synthesis of some fluorine-containing pyridinealdoximes of potential use for the treatment of organophosphorus nerve-agent poisoning

Fluoroheterocyclic aldoximes were screened as therapeutic agents for the treatment of anticholinesterase poisoning. 2-Fluoropyridine-3- and -6-aldoxime, and 3-fluoropyridine-2- and -4-aldoxime, were synthesised. Attempts to obtain 3,5,6-trifluoropyridine-2,4-bis(aldoxime) and -2-aldoxime, however, proved unsuccessful. Pentafluorobenzaldoxime was prepared by oximation of pentafluorobenzaldehyde. Acid dissociation constants (pKa) and second-order rate constants (kox-) of the fluorinated pyridinealdoximes towards sarin were measured. 2,3,5,6-Tetrafluoropyridine-4- aldoxime had the best profile: its kox- approached that of the therapeutic oxime P2S (310 vs. 120 l mol-1 min-1), but its higher pKa (9.1 vs. 7.8) fell short of the target figure of 8 required for reactivation of inhibited acetylcholinesterase in vivo. N-alkylation of the fluorinated pyridine-aldoximes may reduce their pK a nearer to 8 and enhance their therapeutic potential. Crown Copyright

Substituted imidazolylmethyl pyridine and pyrazine deriviatives GABAa receptor ligands

Substituted imidazolylmethyl pyridine and pyrazine derivatives that bind to GABAA receptors are provided. Such compounds may be used to modulate ligand binding to GABAA receptors in vivo or in vitro, and are particularly useful in the treatment of a variety of central nervous system (CNS) disorders in humans, domesticated companion animals and livestock animals. Compounds provided herein may be administered alone or in combination with one or more other CNS agents to potentiate the effects of the other CNS agent(s). Pharmaceutical compositions and methods for treating such disorders are provided, as are methods for using such ligands for detecting GABAA receptors (e.g., receptor localization studies).