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 

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