41404-58-4

Basic information

• Product Name: 2-Bromo-5-fluoropyridine
• Synonyms: 2-BROMO-5-FLUOROPYRIDINE;2--5- fluoropyridinebroMide;2-BroMo-5-fluoropyridine, 97+%;2 - broMine - 5 - fluoride pyridine;5-FLUOROPYRIDIN-2-YL-BORONIC ACID;5-FLUOROPYRIDINE-2-BORONIC ACID;2-bromo-5-fluoropyridin;2-Bromo-5-fluoropyridine98%
• CAS NO: 41404-58-4
• Molecular Formula: C₅H₃BrFN
• Molecular Weight: 175.99
• EINECS: 1533716-785-6
• Product Categories: Fluorin-contained pyridine series;blocks;Bromides;FluoroCompounds;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridine series;Fluorinated;Organohalides;Bromopyridines;Fluoropyridines;Halopyridines;Boronic Acid;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Variety of halogenated heterocyclic series;Fluorine series
• Mol File: 41404-58-4.mol
• Article Data: 5

Chemical Properties

• Melting Point: 30-31 °C(lit.)
• Boiling Point: 80-83 °C44 mm Hg(lit.)
• Flash Point: 167 °F
• Appearance: Colorless to slightly yellow/Liquid
• Density: 1.707 g/cm³
• Vapor Pressure: 1.85mmHg at 25°C
• Refractive Index: 1.5396
• Storage Temp.: Store Cold
• PKA: -1.63±0.10(Predicted)
• BRN: 1561456
• CAS DataBase Reference: 2-Bromo-5-fluoropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-fluoropyridine(41404-58-4)
• EPA Substance Registry System: 2-Bromo-5-fluoropyridine(41404-58-4)

Safety Data

• Hazard Codes: Xi,Xn,F
• Statements: 36/37/38-20/21/22-10
• Safety Statements: 26-36-16
• RIDADR: 2811
• WGK Germany: 3
• HazardClass: IRRITANT
• PackingGroup: III
• Hazardous Substances Data: 41404-58-4(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow Cryst

Uses

Different sources of media describe the Uses of 41404-58-4 differently. You can refer to the following data:
1. 2-Bromo-5-fluoropyridine is used in the synthesis of mGluR5 antagonist for the treatment of neuropathic pain.
2. 2-Bromo-5-fluoropyridine can be used in the synthesis of the following:5-fluoro-2-phenylpyridine via Suzuki coupling reaction with phenylboronic acid5-fluoro-2-(p-tolyl)pyridine via Suzuki coupling reaction with p-tolylboronic acidIt can undergo palladium-catalyzed homo-coupling reaction to give the corresponding biaryl. It can also be employed in a palladium-catayzed α-arylation of esters leading to 4-pyridylcarboxypiperidines.

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

Synthetic route

2-amino-5-fluoropyridine (21717-96-4) → 2-bromo-5-fluoropyridine (41404-58-4)

Conditions	Yield
Stage #1: 2-amino-5-fluoropyridine With hydrogen bromide; bromine; sodium nitrite In water at 0 - 5℃; for 1h; Stage #2: With sodium hydroxide In water at 20℃; for 0.333333h;	66%
Stage #1: 2-amino-5-fluoropyridine With hydrogen bromide; bromine at 0℃; for 0.333333h; Stage #2: With sodium nitrite In water at -10℃; for 2h; Stage #3: With sodium hydroxide In water at 5℃; for 0.5h;	36%
Sandmayer reaction;

2-bromo-5-fluoropyridine (41404-58-4) → 2-bromo-5-fluoro-1-oxido-pyridin-1-ium

Conditions	Yield
With urea hydrogen peroxide adduct; trifluoroacetic anhydride In chloroform at 20℃; for 15h;	100%
With dihydrogen peroxide; trifluoroacetic acid In water at 80℃; for 16h;	90%
With dihydrogen peroxide; trifluoroacetic anhydride In dichloromethane; water at 0 - 20℃; for 18h;	76%

2-bromo-5-fluoropyridine (41404-58-4) + tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate (146553-06-2, 87694-49-3) → tert-butyl N-[(1S)-2-(5-fluoro-2-pyridyl)-1-methyl-2-oxo-ethyl]carbamate

Conditions	Yield
Stage #1: 2-bromo-5-fluoropyridine With TurboGrignard In tetrahydrofuran at 0 - 20℃; for 2.33333h; Inert atmosphere; Stage #2: tert-butyl {(S)-1-[methoxy(methyl)amino]-1-oxopropan-2-yl}carbamate With methylmagnesium bromide In tetrahydrofuran at -20 - 20℃; for 1.5h; Inert atmosphere;	100%

2-bromo-5-fluoropyridine (41404-58-4) + tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3) → C16H23FN2O3 (918501-72-1)

Conditions	Yield
Stage #1: 2-bromo-5-fluoropyridine; tert butyl 4-formylpiperidine-1-carboxylate With n-butyllithium In toluene at -78℃; for 2.5h; Stage #2: With water; acetic acid In toluene at -78℃;	99%

piperidine (110-89-4) + 2-bromo-5-fluoropyridine (41404-58-4) → 5-fluoro-2-(piperidin-1-yl)pyridine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 100℃; for 24h; Inert atmosphere;	99%

1-methyl-piperazine (109-01-3) + 2-bromo-5-fluoropyridine (41404-58-4) → 2-(4-methylpiperazin-1-yl)-5-fluoropyridine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 100℃; for 24h; Inert atmosphere;	99%

2-bromo-5-fluoropyridine (41404-58-4) + N-butylamine (109-73-9) → 2-(n-butylamino)-5-fluoropyridine

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 100℃; for 24h; Inert atmosphere;	99%

2-bromo-5-fluoropyridine (41404-58-4) → 5,5’-difluoro-2,2’-bipyridine (1041837-79-9)

Conditions	Yield
With palladium 10% on activated carbon; potassium acetate; bis(pinacol)diborane In ethanol at 60℃; for 18h; Suzuki-Miyaura Coupling; Inert atmosphere;	98.2%
With indium; lithium chloride; palladium diacetate In N,N-dimethyl-formamide at 100℃; for 1h;	89%
With indium; palladium diacetate; lithium chloride In N,N-dimethyl-formamide at 100℃; for 2h; Inert atmosphere;	80%

2-bromo-5-fluoropyridine (41404-58-4) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → 4-(5-fluoropyridin-2-yl)-N,N-diphenylaniline (1263145-39-6)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃; for 0.2h; Suzuki reaction;	98%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.166667h; Suzuki Coupling;	92%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; Suzuki Coupling;

2-bromo-5-fluoropyridine (41404-58-4) + tert-Butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-1(2H)-pyridinecarboxylate (375853-82-0, 286961-14-6) → tert-butyl 5-fluoro-3',6'-dihydro-[2,4'-bipyridine]-1'(2'H)carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran at 90℃; for 48h;	98%

2-bromo-5-fluoropyridine (41404-58-4) + (4-ethoxy-4-oxobutyl)zinc(II) bromide (151073-69-7) → ethyl 4-(5-fluoropyridin-2-yl)butanoate (1100766-36-6)

Conditions	Yield
[1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride In tetrahydrofuran at 20℃; for 48h; Negishi Coupling Reaction;	97%
With [1,3-bis(2,6-diisopropyl-phenyl)imidazol-2-ylidene](3-chloropyridyl)-palladium(II) dichloride In tetrahydrofuran at 20℃; for 48h; Negishi coupling;	80%

2-bromo-5-fluoropyridine (41404-58-4) + 4-methylphenylboronic acid (5720-05-8) → 5-fluoro-2-(4-methylphenyl)pyridine (1198348-26-3)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 70℃; for 8h;	97%
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 0.166667h; Suzuki coupling;	96%
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 0.0833333h; Suzuki coupling;	93%
Stage #1: 2-bromo-5-fluoropyridine With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 0.25h; Suzuki Coupling; Inert atmosphere; Stage #2: 4-methylphenylboronic acid In ethanol; water; toluene at 80℃; for 48h; Suzuki Coupling; Inert atmosphere;	67%

2-bromo-5-fluoropyridine (41404-58-4) + 2-triethylsilylacetylene (1777-03-3) → 5-fluoro-2-[2-(triethylsilyl)ethynyl]pyridine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h; Inert atmosphere;	97%

n-butyllithium (109-72-8, 29786-93-4) + 2-bromo-5-fluoropyridine (41404-58-4) + Triisopropyl borate (5419-55-6) → lithium triisopropyl 2-(5-fluoropyridyl) borate

Conditions	Yield
In tetrahydrofuran; toluene 1. triisopropylborate, toluene/THF 4/1; 2. n-C4H9Li over 90 min, -78°C to room temp.;	96%

2-bromo-5-fluoropyridine (41404-58-4) + triethylsilyl chloride (994-30-9) → 2-bromo-5-fluoro-4-(triethylsilyl)pyridine (1387561-09-2)

Conditions	Yield
Stage #1: 2-bromo-5-fluoropyridine With n-butyllithium; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at -75 - -50℃; for 1h; Stage #2: triethylsilyl chloride With ammonium chloride In water at -50 - -20℃; Product distribution / selectivity;	96%
Stage #1: 2-bromo-5-fluoropyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -78 - -50℃; for 1h; Stage #2: triethylsilyl chloride In tetrahydrofuran; hexane at -78 - -20℃;	96%
Stage #1: 2-bromo-5-fluoropyridine With n-butyllithium; diisopropylamine In tetrahydrofuran at -70℃; for 1h; Stage #2: triethylsilyl chloride In tetrahydrofuran at -70 - -30℃; for 1.5h;

2-bromo-5-fluoropyridine (41404-58-4) + 4-biphenylboronic acid (5122-94-1) → 5-fluoro-2-(4-phenylphenyl)pyridine (1101205-31-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 70℃; for 8h;	96%

2-bromo-5-fluoropyridine (41404-58-4) + 2-(phenoxymethyl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (1382782-07-1) → 5-(5-fluoro-2-pyridyl)-2-(phenoxymethyl)-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one (1382782-16-2)

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In toluene at 120℃; for 60h; Inert atmosphere; Sealed tube;	96%

2-bromo-5-fluoropyridine (41404-58-4) + 2-(adamantan-1-yloxy)ethan-1-amine (25225-13-2) → N-[2-(adamantan-1-yloxy)ethyl]-5-fluoropyridin-2-amine

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; DavePhos In 1,4-dioxane for 12h; Reflux; Schlenk technique;	95%

2-bromo-5-fluoropyridine (41404-58-4) + 1-tert-Butyl 4-methyl piperidine-1,4-dicarboxylate (124443-68-1) → 5-fluoro-2',3',5',6'-tetrahydro-[2,4']bipyridinyl-1',4'-dicarboxylic acid 1'-tert-butyl ester 4'-methyl ester

Conditions	Yield
With lithium hexamethyldisilazane; tris-(dibenzylideneacetone)dipalladium(0); tri-tert-butyl phosphine In toluene at 23℃; for 12h;	93%

2-bromo-5-fluoropyridine (41404-58-4) + (7S)-5-(3,4-dichlorophenyl)-7-methyl-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazine-3-carboxamide → (7S)-5-(3,4-dichlorophenyl)-N-(5-fluoro-2-pyridyl)-7-methyl-4-oxo-6,7-dihydropyrazolo[1,5-a]pyrazine-3-carboxamide

Conditions	Yield
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In tetrahydrofuran at 90℃; for 4h; Goldberg Reaction; Sealed tube; Inert atmosphere;	93%

2-bromo-5-fluoropyridine (41404-58-4) + 2-methyl-but-3-yn-2-ol (115-19-5) → dimethylhydroxymethyl-5-fluoro-2-pyridylacetylene (904694-30-0)

Conditions	Yield
With piperidine; tetrakis(triphenylphosphine) palladium(0) at 80℃; for 1h;	92%

2-bromo-5-fluoropyridine (41404-58-4) + phenylboronic acid (98-80-6) → 2-phenyl-5-fluoropyridine (512171-81-2)

Conditions	Yield
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 0.166667h; Suzuki coupling;	92%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Suzuki Coupling; Inert atmosphere; Reflux;	92%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol at 100℃; for 15h; Inert atmosphere;	91%

2-bromo-5-fluoropyridine (41404-58-4) + 3-fluorophenylboronic acid (768-35-4) → 5-fluoro-2-(3-fluorophenyl)pyridine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80 - 100℃; for 3h; Inert atmosphere;	92%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 80 - 100℃; for 3h; Inert atmosphere;	92%

2-bromo-5-fluoropyridine (41404-58-4) + Ethyl diethoxyacetate (6065-82-3) → 1-(2-bromo-5-fluoropyridin-4-yl)-2,2-diethoxyethan-1-one

Conditions	Yield
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h;	92%
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h; Inert atmosphere;	92%
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h;	92%
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tetrahydrofuran at -78℃; for 1.5h; Inert atmosphere; Stage #2: Ethyl diethoxyacetate In tetrahydrofuran at -78℃; for 2h;	92%

2-bromo-5-fluoropyridine (41404-58-4) + carbon dioxide (124-38-9) → 2-bromo-5-fluoropyridine-4-carboxylic acid (885588-12-5)

Conditions	Yield
Stage #1: 2-bromo-5-fluoropyridine With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -70 - -60℃; for 1.5h; Stage #2: carbon dioxide In tetrahydrofuran; hexane at -70 - 20℃;	92%

2-bromo-5-fluoropyridine (41404-58-4) + mesitylenesulfonylhydroxylamine (36016-40-7) → 2-bromo-5-fluoro-pyridin-1-ium-1-amine 2,4,6-trimethylbenzenesulfonate

Conditions	Yield
In dichloromethane at 10℃; for 18h; Inert atmosphere;	92%
In dichloromethane at 10℃; for 18h;	92%
In dichloromethane at 10℃; for 18h;	90 g

2-bromo-5-fluoropyridine (41404-58-4) + para-nitrobenzenethiol (1849-36-1) → C11H7BrN2O2S

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide at 90℃; for 12h;	91.8%

4-(carbazol-9-yl)phenylboronic acid (419536-33-7) + 2-bromo-5-fluoropyridine (41404-58-4) → 9-(4-(5-fluoropyridin-2-yl)phenyl)-9H-carbazole (1380225-66-0)

Conditions	Yield
With palladium diacetate; potassium carbonate In ethanol; water at 80℃; for 0.166667h; Suzuki Coupling;	91%
With palladium diacetate; potassium carbonate In ethanol; water at 80℃;

2-bromo-5-fluoropyridine (41404-58-4) + (RS)-2-methylpropane-2-sulfinic acid [2-(tert-butyldimethylsilanyloxy)ethylidene]amide (1075756-68-1) → N-(2-(tert-butyldimethylsilyloxy)-1-(5-fluoropyridin-2-yl)ethyl)-2-methylpropane-2-sulfinamide (1075756-79-4)

Conditions	Yield
Stage #1: 2-bromo-5-fluoropyridine With lithium diisopropyl amide In tert-butyl methyl ether; pentane at -78℃; for 0.5h; Stage #2: (RS)-2-methylpropane-2-sulfinic acid [2-(tert-butyldimethylsilanyloxy)ethylidene]amide In tert-butyl methyl ether; pentane at -78℃; for 2h;	90%

2-bromo-5-fluoropyridine (41404-58-4) + tributyl(1-ethoxyvinyl)stannane (97674-02-7) → 2-(1-ethoxyvinyl)-5-fluoropyridine

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In acetonitrile at 80℃; for 30h;	90%

2-bromo-5-fluoropyridine (41404-58-4) + sodium thioethylate (811-51-8) → 2-bromo-5-(ethylthio)pyridine (1346539-39-6)

Conditions	Yield
In N,N-dimethyl-formamide at 100℃; for 15h; Inert atmosphere;	90%
In N,N-dimethyl-formamide at 100℃; for 15h;	90%
In N,N-dimethyl-formamide at 100℃; for 15h;	90%
In N,N-dimethyl-formamide at 100℃; for 15h;	90%

Upstream product

• 21717-96-4 2-amino-5-fluoropyridine 

Downstream Products

• 915720-54-6 1-(5-fluoropyridin-2-yl)ethan-1-one 
• 885588-71-6 5-fluoro-2-(4-methoxyphenyl)pyridine 
• 907208-90-6 1-(5-fluoropyridine-2-yl)piperazine 
• 936107-43-6 C₂₆H₂₂Cl₂FN₃ 
• 936343-00-9 4-(5-fluoro-pyridin-2-yloxymethyl)-benzonitrile 
• 791819-04-0 5-fluoro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 1379667-32-9 N-[2-(5-fluoropyridin-2-yl)phenyl]-4-methylbenzenesulfonamide 
• 1416732-34-7 2-(2,4-difluorophenyl)-1,1-difluoro-1-(5-fluoropyridin-2-yl)-3-(1H-tetrazol-1-yl)propan-2-ol 
• 1416732-35-8 C₁₃H₆F₅NO 
• 1416732-36-9 C₁₄H₈F₅NO 
• 1496617-69-6 C₄₆H₃₂Cl₂F₂N₄Pt₂ 
• 1610611-10-3 N-ethyl-N-(5-fluoropyridin-2-yl)-3-(4-(methylcarbamoyl)phenyl)pyrazolo[1,5-a]pyridine-5-carboxamide 
• 1251039-74-3 5-fluoro-N-isopropylpyridin-2-amine 
• 1381970-61-1 N-{2-[4-(5-fluoropyridin-2-yl)-1H-pyrazol-1-yl]ethyl}-5-methyl-2-(2H-1,2,3-triazol-2-yl)benzamide 

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