766-11-0

Basic information

• Product Name: 2-Fluoro-5-bromopyridine
• Synonyms: 5-BROMO-2-FLUOROPYRIDINE;3-BROMO-6-FLUOROPYRIDINE;2-FLUORO-5-BROMO PYRIDINE;3-fluoro-5-bromopyridine;5-Bromo-2-fluoropyridine,98%;2-FLUORO-5-BORMOPYRIDINE;5-BROMO-2-FLUOROPYRIDINE 99%;5-Bromo-2-fluoropyridine,99%
• CAS NO: 766-11-0
• Molecular Formula: C₅H₃BrFN
• Molecular Weight: 175.99
• EINECS: 1308068-626-2
• Product Categories: Fluorin-contained pyridine series;blocks;Bromides;Pyridines;Pyridine;pharmacetical;Pyridines derivates;Halogenated;Organohalides;Bromopyridines;Fluoropyridines;Halopyridines;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Variety of halogenated heterocyclic series;Pyridine Series;Fluorine series
• Mol File: 766-11-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 162-164 °C750 mm Hg(lit.)
• Flash Point: 165 °F
• Appearance: Clear colorless yellow/Liquid
• Density: 1.71 g/mL at 25 °C(lit.)
• Vapor Pressure: 1.37mmHg at 25°C
• Refractive Index: n20/D 1.5325(lit.)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO (Slightly), Methanol (Slightly)
• PKA: -2.79±0.10(Predicted)
• BRN: 1363171
• CAS DataBase Reference: 2-Fluoro-5-bromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Fluoro-5-bromopyridine(766-11-0)
• EPA Substance Registry System: 2-Fluoro-5-bromopyridine(766-11-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-22
• Safety Statements: 26-36/37-37/39
• RIDADR: UN2810
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 766-11-0(Hazardous Substances Data)

Usage

Chemical Properties

Clear colorless yellowish liquid

Uses

2-Fluoro-5-bromopyridine is used in the synthesis of heteroaromatic and aniline derivatives of piperidines as potent ligands used for vesicular acetylcholine transport. Also used in the synthesis of benzofurano[3,2-d]pyrimidin-2-one derived inhbitors.

InChI:InChI=1/C5H3BrFN/c6-4-1-2-5(7)8-3-4/h1-3H

Synthetic route

5-bromo2-nitropyridine (39856-50-3) → 5-bromo-2-fluoropyridine (766-11-0)

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran; water; N,N-dimethyl-formamide at 23℃; for 4h;
With p-methoxybenzoyl fluoride; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;	91 %Spectr.

6-fluoronicotinic acid (403-45-2) → 5-bromo-2-fluoropyridine (766-11-0)

Conditions	Yield
With bromine; mercury(II) oxide In tetrachloromethane; hexane	1.73 g (63%)

5-bromo-2-chloropyridine (53939-30-3) → 5-bromo-2-fluoropyridine (766-11-0)

Conditions	Yield
With p-methoxybenzoyl fluoride; 2,3-Dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene In N,N-dimethyl-formamide at 25℃; for 16h; Inert atmosphere;	80 %Spectr.
With tetramethylammonium fluoride In N,N-dimethyl-formamide at 25℃; for 24h; Sealed tube;	100 %Spectr.

3-Hydroxytetrahydrofuran (453-20-3) + 5-bromo-2-fluoropyridine (766-11-0) → rac-5-bromo-2-(tetrahydro-furan-3-yloxy)-pyridine (494771-98-1)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 72h;	100%
With caesium carbonate In N,N-dimethyl-formamide at 90℃; for 70h; Sealed tube; Inert atmosphere;	93%

5-bromo-2-fluoropyridine (766-11-0) + 4-trifluoromethoxyphenylboronic acid (139301-27-2) → 2-fluoro-5-[4-(trifluoromethoxy)phenyl]pyridine (1261592-34-0)

Conditions	Yield
With sodium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In ethanol; water; toluene at 85 - 88℃; for 3h; Inert atmosphere;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium carbonate In ethanol; toluene at 85 - 88℃; for 3h; Suzuki Coupling; Inert atmosphere;	100%

5-bromo-2-fluoropyridine (766-11-0) + C20H24BrNO6 (1431434-20-6) → C23H22BrFN2O5 (1431434-25-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78℃;	100%
With n-butyllithium In tetrahydrofuran at -78℃;

5-bromo-2-fluoropyridine (766-11-0) + 3,4-dichlorobenzyl alcohol (1805-32-9) → 5-bromo-2-(3,4-dichlorobenzyloxy)pyridine

Conditions	Yield
Stage #1: 3,4-dichlorobenzyl alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	100%

5-bromo-2-fluoropyridine (766-11-0) + (3,4,5-trimethoxyphenyl)methanol (3840-31-1) → 5-bromo-2-(3,4,5-trimethoxybenzyloxy)pyridine

Conditions	Yield
Stage #1: (3,4,5-trimethoxyphenyl)methanol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	100%

5-bromo-2-fluoropyridine (766-11-0) + phenylmethanethiol (100-53-8) → 2-(benzylsulfanyl)-5-bromopyridine (874959-69-0)

Conditions	Yield
Stage #1: phenylmethanethiol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	100%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 2h;

5-bromo-2-fluoropyridine (766-11-0) + cuminol (536-60-7) → C15H16BrNO

Conditions	Yield
Stage #1: cuminol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: 5-bromo-2-fluoropyridine In N,N-dimethyl-formamide; mineral oil at 20℃; for 72h;	100%
Stage #1: cuminol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1h; Stage #2: 5-bromo-2-fluoropyridine In N,N-dimethyl-formamide; mineral oil at 20℃; for 72h;	100%

5-bromo-2-fluoropyridine (766-11-0) + 4-trifluoromethylphenylboronic acid (128796-39-4) → 2-fluoro-5-(4-(trifluoromethyl)phenyl)pyridine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; water; sodium carbonate In ethanol; toluene at 85 - 88℃; for 3h; Suzuki Coupling; Inert atmosphere;	100%

3-methyl-butane-1,3-diol (2568-33-4) + 5-bromo-2-fluoropyridine (766-11-0) → 4-(5-bromopyridin-2-yloxy)-2-methylbutan-2-ol

Conditions	Yield
Stage #1: 3-methyl-butane-1,3-diol With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: 5-bromo-2-fluoropyridine In N,N-dimethyl-formamide at 0 - 20℃; for 18h; Inert atmosphere;	100%

5-bromo-2-fluoropyridine (766-11-0) + tert-butyl (1R,5S,6R)-3-azabicyclo[3.1.0]hexan-6-ylcarbamate (134575-17-0) → tert-butyl ((1R,5S,6s)-3-(5-bromopyridin-2-yl)-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 4h;	100%

5-bromo-2-fluoropyridine (766-11-0) + formic acid ethyl ester (109-94-4) → 5-bromo-2-fluoro-pyridine-3-carbaldehyde (875781-15-0)

Conditions	Yield
Stage #1: 5-bromo-2-fluoropyridine With n-butyllithium; diisopropylamine In tetrahydrofuran at -78 - 0℃; for 0.666667h; Stage #2: formic acid ethyl ester In tetrahydrofuran at -78℃; for 0.0333333h; Product distribution / selectivity;	99%
Stage #1: 5-bromo-2-fluoropyridine With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -78℃; for 0.5h; Stage #2: formic acid ethyl ester In tetrahydrofuran at -78℃; for 0.166667h;	88%
Stage #1: 5-bromo-2-fluoropyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -65 - 0℃; for 1.5h; Stage #2: formic acid ethyl ester In tetrahydrofuran; hexane for 0.166667h; Product distribution / selectivity;	85%

4-carbethoxypiperidine (1126-09-6) + 5-bromo-2-fluoropyridine (766-11-0) → ethyl 1-(5-bromopyridin-2-yl)piperidine-4-carboxylate (364794-70-7)

Conditions	Yield
In pyridine at 190℃; for 1h; Inert atmosphere; Microwave irradiation; sealed vial;	99%
With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 6h; Inert atmosphere;	76%

5-bromo-2-fluoropyridine (766-11-0) + 2-methoxyethylamine (109-85-3) → 5-bromo-N-(2-methoxyethyl)pyridin-2-amine (1005010-02-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 180℃; for 2h;	99%
With N-ethyl-N,N-diisopropylamine In dimethyl sulfoxide at 135℃; for 4h;	90%

Thien-3-ylboronic acid (6165-69-1) + 5-bromo-2-fluoropyridine (766-11-0) → 2-fluoro-5-(thiophen-3-yl)pyridine

Conditions	Yield
With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); tetrabutylammomium bromide In 1-methyl-pyrrolidin-2-one; water; toluene at 90℃; Suzuki-Miyaura cross-coupling; Continuous flow reactor; Inert atmosphere;	99%

tetrahydropyran-4-carboxylic acid methyl ester (110238-91-0) + 5-bromo-2-fluoropyridine (766-11-0) → methyl 4-(5-bromo-2-pyridyl)tetrahydropyran-4-carboxylate (1382486-55-6)

Conditions	Yield
With potassium hexamethylsilazane In tetrahydrofuran at -30 - 20℃; for 3h;	99%
With potassium hexamethylsilazane In tetrahydrofuran at -30 - 20℃; for 3h;	99%

5-bromo-2-fluoropyridine (766-11-0) + ethyl 2-hydroxyacetate (623-50-7) → ethyl 2-((5-bromopyridin-2-yl)oxy)acetate

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 23℃; for 4h;	99%
With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 6h; Time;

1,2-dimethyl-1H-imidazole (1739-84-0) + 5-bromo-2-fluoropyridine (766-11-0) → 5-(1,2-dimethyl-1H-imidazol-5-yl)-2-fluoropyridine

Conditions	Yield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	99%

5-bromo-2-fluoropyridine (766-11-0) + para-Chlorobenzyl alcohol (873-76-7) → 2-(4-chlorobenzyloxy)-5-bromopyridine

Conditions	Yield
Stage #1: para-Chlorobenzyl alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	98%

5-bromo-2-fluoropyridine (766-11-0) + 4-fluorobenzylic alcohol (459-56-3) → 5-bromo-2-((4-fluorobenzyl)oxy)pyridine (936343-08-7)

Conditions	Yield
Stage #1: 4-fluorobenzylic alcohol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	98%
Stage #1: 4-fluorobenzylic alcohol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran; mineral oil at 0 - 80℃; for 3h;

piperonol (495-76-1) + 5-bromo-2-fluoropyridine (766-11-0) → 2-(1,3-benzodioxol-5-ylmethoxy)-5-bromopyridine

Conditions	Yield
Stage #1: piperonol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	98%

5-bromo-2-fluoropyridine (766-11-0) + 6-(1H-pyrazole-5-carbonyl)-3H-1,3-benzothiazol-2-one hydrochloride → 6-[1-(5-bromo-2-pyridyl)pyrazole-3-carbonyl]-3H-1,3-benzothiazol-2-one

Conditions	Yield
Stage #1: 6-(1H-pyrazole-5-carbonyl)-3H-1,3-benzothiazol-2-one hydrochloride With potassium carbonate In N,N-dimethyl-formamide at 40℃; for 0.75h; Stage #2: 5-bromo-2-fluoropyridine In N,N-dimethyl-formamide at 130℃; for 10h;	98%

5-bromo-2-fluoropyridine (766-11-0) + 3-Formylphenylboronic acid (87199-16-4) → C12H8FNO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In water; toluene at 90℃; for 5h; Inert atmosphere;	98%

5-bromo-2-fluoropyridine (766-11-0) + tert-butyl (3R)-3-[3-hydroxyphenyl]-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (1227471-85-3) → tert-butyl (3R)-3-{3-[(5-bromopyridin-2-yl)oxy]phenyl}-1-oxa-8-azaspiro[4.5]decane-8-carboxylate (1227471-90-0)

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 20℃;	97%

propan-1-ol (71-23-8) + 5-bromo-2-fluoropyridine (766-11-0) → 5-bromo-2-propoxy-pyridine (850142-79-9)

Conditions	Yield
Stage #1: propan-1-ol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	97%

5-bromo-2-fluoropyridine (766-11-0) + 2-phenylethanol (60-12-8) → 5-bromo-2-(2-phenylethoxy)pyridine

Conditions	Yield
Stage #1: 2-phenylethanol With sodium hydride In tetrahydrofuran at 0 - 20℃; for 1.5h; Reflux; Stage #2: 5-bromo-2-fluoropyridine In tetrahydrofuran for 12h; Reflux;	97%

2-methyl-1-phenyl-1H-imidazole (60053-07-8) + 5-bromo-2-fluoropyridine (766-11-0) → 2-fluoro-5-(2-methyl-1-phenyl-1H-imidazol-5-yl)pyridine

Conditions	Yield
With C68H65Cl2N3Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; regioselective reaction;	97%

3,6-diazabicyclo[3.1.1]heptane-6-carboxylic acid tert-butyl ester (869494-16-6) + 5-bromo-2-fluoropyridine (766-11-0) → tert-butyl 3-(5-bromopyridin-2-yl)-3,6-diazabicyclo[3.1.1]heptane-6-carboxylate

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 24h;	97%
With potassium carbonate In dimethyl sulfoxide at 90℃; for 24h;	97%

5-bromo-2-fluoropyridine (766-11-0) + tert-butyl(dimethyl){2-[trans-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclopropyl]ethoxy}silane → 5-[trans-2-(2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)cyclopropyl]-2-fluoropyridine

Conditions	Yield
With palladium diacetate; caesium carbonate; catacxium A In tert-Amyl alcohol; water at 20 - 75℃; for 16h; Inert atmosphere;	97%
With palladium diacetate; caesium carbonate; catacxium A In tert-Amyl alcohol; water at 75℃; for 16h; Suzuki Coupling; Inert atmosphere;	25%

5-bromo-2-fluoropyridine (766-11-0) + 6-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyridine → 4-(6-fluoropyridin-3-yl)-6-methoxypyrazolo[1,5-a]pyridine

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 90℃; Inert atmosphere;	96.97%

5-bromo-2-fluoropyridine (766-11-0) + 3-phenylpyrazole (2458-26-6) → 5-bromo-2-(3-phenyl-1H-pyrazol-1-yl)pyridine

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide at 180℃; for 8.5h; Inert atmosphere; Schlenk technique;	96%

Upstream product

• 39856-50-3 5-bromo2-nitropyridine 
• 53939-30-3 5-bromo-2-chloropyridine 
• 223463-13-6 2-iodo-5-bromopyridine 
• 624-28-2 2,5-dibromopyridine 
• 403-45-2 6-fluoronicotinic acid 

Downstream Products

• 36404-90-7 2-fluoropyridine-3-carboxaldehyde 
• 351019-18-6 (6-fluoropyridin-3-yl)boronic acid 
• 501435-91-2 5-bromo-2-fluoropyridin-3-ylboronic acid 
• 54856-82-5 3-methyl-[1,2,3]triazolo[1,5-a]pyridine 
• 827628-15-9 1-(5-bromopyridin-2-yl)cyclopropane-1-carbonitrile 
• 790262-66-7 2-fluoro-5-(1-trityl-1H-imidazol-4-yl)pyridine 
• 361147-22-0 2-fluoro-3-phenylpyridine 
• 501436-05-1 5-bromo-2-fluoro-3-(4'-methoxyphenyl)pyridine 
• 501436-01-7 5-bromo-2-fluoro-3-(4'-nitrophenyl)pyridine 
• 501436-09-5 2-fluoro-3-(4'-methoxyphenyl)-5-phenylpyridine 
• 501435-94-5 2-fluoro-5-(4''-methylphenyl)-3-(4'-nitrophenyl)pyridine 
• 1038395-61-7 C₁₅H₉B₃F₃N₃O₃ 
• 83664-33-9 2-(benzyloxy)-5-bromopyridine 
• 847687-65-4 (2S)-2-[(S)-[(5-bromopyridin-2-yl)thio](phenyl)methyl]-4-(phenylmethyl)morpholine 

Relevant articles and documents

Tetramethylammonium Fluoride Alcohol Adducts for SNAr Fluorination

Nucleophilic aromatic fluorination (SNAr) is among the most common methods for the formation of C(sp2)-F bonds. Despite many recent advances, a long-standing limitation of these transformations is the requirement for rigorously dry, aprotic conditions to maintain the nucleophilicity of fluoride and suppress the generation of side products. This report addresses this challenge by leveraging tetramethylammonium fluoride alcohol adducts (Me4NF·ROH) as fluoride sources for SNAr fluorination. Through systematic tuning of the alcohol substituent (R), tetramethylammonium fluoride tert-amyl alcohol (Me4NF·t-AmylOH) was identified as an inexpensive, practical, and bench-stable reagent for SNAr fluorination under mild and convenient conditions (80 °C in DMSO, without the requirement for drying of reagents or solvent). A substrate scope of more than 50 (hetero) aryl halides and nitroarene electrophiles is demonstrated.

Acyl azolium fluorides for room temperature nucleophilic aromatic fluorination of chloro- and nitroarenes

The reaction of acid fluorides with N-heterocyclic carbenes (NHCs) produces anhydrous acyl azolium fluorides. With appropriate selection of acid fluoride and NHC, these salts can be used for the room temperature SNAr fluorination of a variety of aryl chlorides and nitroarenes.

Tetrabutylammonium salt induced denitration of nitropyridines: Synthesis of fluoro-, hydroxy-, and methoxypyridines

(Chemical Equation Presented) An efficient method for the synthesis of fluoropyridines via the fluorodenitration reaction is reported. The reaction is mediated by tetrabutylammonium fluoride (TBAF) under mild conditions without undue regard to the presence of water. The fluorodenitration is general for 2- or 4-nitro-substituted pyridines, while 3-nitropyridines require attendant electron-withdrawing groups for the reaction to proceed efficiently. Nitropyridines also undergo hydroxy- and methoxydenitration under mild conditions in the presence of the corresponding tetrabutylammonium species.