40473-01-6

Basic information

• Product Name: 2-Bromo-5-chloropyridine
• Synonyms: 2-BROMO-5-CHLOROPYRIDINE;IFLAB-BB F2124-0201;2-Brome-5-chloropyridine;2-BROMO-5-CHLOROPYRIDINE, 98.5%;2-Bromo-5-chloropyridine,98%;2-BroMoo-5-chloropyridine;2-BroMo-5-chloropyridine, 98% 5GR;2-broMo-5-chloropyridin
• CAS NO: 40473-01-6
• Molecular Formula: C₅H₃BrClN
• Molecular Weight: 192.44
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Pyridine Series;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Bromopyridines;Chloropyridines;Halopyridines;Boronic Acid
• Mol File: 40473-01-6.mol
• Article Data: 14

Chemical Properties

• Melting Point: 65-69 °C
• Boiling Point: 128 °C / 16mmHg
• Flash Point: 82 °C
• Appearance: Beige to yellow-brown/Powder
• Density: 1.736 g/cm³
• Vapor Pressure: 0.257mmHg at 25°C
• Refractive Index: 1.581
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: -1.49±0.10(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: 2-Bromo-5-chloropyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromo-5-chloropyridine(40473-01-6)
• EPA Substance Registry System: 2-Bromo-5-chloropyridine(40473-01-6)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/37/38-20/22-20/2236/37/38-20/21/22
• Safety Statements: 36/37/39-26-22-22 26 36/37/39-36
• RIDADR: Cool, dry,tightly closed
• HazardClass: IRRITANT
• Hazardous Substances Data: 40473-01-6(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powder

Uses

It is an important organic intermediate used in agrochemicals, pharmaceuticals and dyestuff fields. It is also used in the synthesis of novel halopyridinylboronic acids and esters.

InChI:InChI=1/C5H3BrClN/c6-5-2-1-4(7)3-8-5/h1-3H

Synthetic route

5-chloro-2-pyridylamine (1072-98-6) → 2-Bromo-5-chloro-pyridine (40473-01-6)

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite In water at 0 - 10℃; for 1.5h;	93%
Stage #1: 5-chloro-2-pyridylamine With hydrogen bromide; bromine; sodium nitrite In water at 0℃; for 1h; Stage #2: With sodium hydroxide In water; ethyl acetate	91%
With hydrogen bromide; bromine; sodium nitrite In water at 0℃; for 1h;	91%

5-chloro-2-pyridylamine (1072-98-6) → 2-Bromo-5-chloro-pyridine (40473-01-6) + 2-bromo-1,3-benzothiazole (2516-40-7)

Conditions	Yield
	A 70% B n/a

2,5 dichloropyridine (16110-09-1) → 2-Bromo-5-chloro-pyridine (40473-01-6)

Conditions	Yield
With trimethylsilyl bromide In various solvent(s) Heating;	67%

5-chloro-2-pyridinol (4214-79-3) → 2-Bromo-5-chloro-pyridine (40473-01-6)

Conditions	Yield
With phosphorus(V) oxybromide for 16h; Heating / reflux;

propanal (5-chloropyridin-2-yl)hydrazone → 2-Bromo-5-chloro-pyridine (40473-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid / 0.08 h / 160 - 180 °C 2: bromine; hydrogen bromide; sodium nitrite / water / 1.5 h / 0 - 10 °C View Scheme

butanal (5-chloropyridin-2-yl)hydrazone → 2-Bromo-5-chloro-pyridine (40473-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid / 0.08 h / 160 - 180 °C 2: bromine; hydrogen bromide; sodium nitrite / water / 1.5 h / 0 - 10 °C View Scheme

phenylethanal (5-chloropyridin-2-yl)hydrazone → 2-Bromo-5-chloro-pyridine (40473-01-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: polyphosphoric acid / 0.08 h / 160 - 180 °C 2: bromine; hydrogen bromide; sodium nitrite / water / 1.5 h / 0 - 10 °C View Scheme

2-Bromo-5-chloro-pyridine (40473-01-6) + triphenylbismuthane (603-33-8) → 5-chloro-2-phenylpyridine (58254-76-5)

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;	98%

2-Bromo-5-chloro-pyridine (40473-01-6) + 3-(5-bromofuran-2-yl)-benzonitrile (453568-66-6) → 3-(5-(5-choro-2-pyridyl)-2-furyl)-benzonitrile (453568-67-7)

Conditions	Yield
With hexamethyldistannane; Pd(PPh3)4 In hexane; dichloromethane; chloroform; ethyl acetate	97.5%

2-Bromo-5-chloro-pyridine (40473-01-6) + tris(4-chlorophenyl)bismuthane (5575-51-9) → 5-chloro-2-(4-chlorophenyl)pyridine

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;	96%

2-Bromo-5-chloro-pyridine (40473-01-6) + 2-vinylbenzeneboronic acid (15016-42-9) → 5-chloro-2-(2-vinylphenyl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In ethanol; toluene at 100℃; for 8h; Inert atmosphere;	96%

2-Bromo-5-chloro-pyridine (40473-01-6) + tris-(4-ethoxy-phenyl)-bismuthine (90591-48-3) → 5-chloro-2-(4-ethoxyphenyl)pyridine

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;	95%

2-Bromo-5-chloro-pyridine (40473-01-6) + phenylboronic acid (98-80-6) → 5-chloro-2-phenylpyridine (58254-76-5)

Conditions	Yield
With [Pd(N-(3-chloro-2-quinoxalinyl)-N'-(2,6-diisopropylphenyl)imidazolium)(PPh3)Cl2]; potassium carbonate In water at 70℃; for 3h; Catalytic behavior; Suzuki-Miyaura Coupling;	94%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Suzuki Coupling; Reflux; Inert atmosphere;
With potassium phosphate tribasic heptahydrate; palladium diacetate In water; isopropyl alcohol at 80℃;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 2h; Schlenk technique; Inert atmosphere; Reflux;

2-Bromo-5-chloro-pyridine (40473-01-6) + methanol (67-56-1) + carbon monoxide (201230-82-2) → methyl 5-chloropyridine-2-carboxylate (132308-19-1)

Conditions	Yield
With triethylamine; palladium diacetate; 1,1'-bis(diphenylphosphino)ferrocene at 50℃; under 775.743 Torr; for 24h;	93%
With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate at 50℃; under 775.743 Torr; for 24h;	93%
With triethylamine; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate at 50℃; under 775.743 Torr; for 24h;	93%

2-Bromo-5-chloro-pyridine (40473-01-6) + indole-2,3-dione (91-56-5) → 8-chloro-11H-pyrido[2,1-b]quinazoline-11-one

Conditions	Yield
With copper(II) acetate monohydrate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; for 10h;	91%

2-Bromo-5-chloro-pyridine (40473-01-6) + 5-methoxyisatine (39755-95-8) → 8-chloro-2-methoxy-11H-pyrido[2,1-b]quinazolin-11-one

Conditions	Yield
With copper(II) acetate monohydrate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; for 10h;	91%

2-Bromo-5-chloro-pyridine (40473-01-6) + (R)-ethyl 3-(3-amino-5-fluoro-4-(isobutyl(tetrahydro-2H-pyran-4-yl)amino)phenyl)butanoate → (R)-ethyl 3-(3-((5-chloropyridin-2-yl)amino)-5-fluoro-4-(isobutyl(tetrahydro-2H-pyran-4-yl)amino)phenyl)butanoate

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 100℃; for 1h; Inert atmosphere;	91%

2-Bromo-5-chloro-pyridine (40473-01-6) + ethyl 4-formyl-1H-pyrazol-3(5)-carboxylate (179692-09-2) → ethyl 1-(5-chloropyridin-2-yl)-4-formyl-1H-pyrazole-3-carboxylate (1224172-54-6)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 2h;	90%
With potassium carbonate In N,N-dimethyl-formamide at 120℃; for 2h;	90%

2-Bromo-5-chloro-pyridine (40473-01-6) + 2-chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (652148-92-0) → 5,6′-dichloro-2,2′-bipyridine

Conditions	Yield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); triethylamine In tetrahydrofuran; water at 20℃; for 2h; Suzuki-Miyaura Coupling; Inert atmosphere; chemoselective reaction;	90%

2-Bromo-5-chloro-pyridine (40473-01-6) + 4-Phenyl-1-butyne (16520-62-0) → 5-chloro-2-(4-phenylbut-1-yn-1-yl)pyridine (1428857-25-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 20℃; for 0.5h; Sonogashira Cross-Coupling;	89%

1,4-diaza-bicyclo[2.2.2]octane (280-57-9) + 2-Bromo-5-chloro-pyridine (40473-01-6) + potassium phtalimide (1074-82-4) → 2-(2-(4-(5-chloropyridin-2-yl)piperazin-1-yl)ethyl)isoindoline-1,3-dione

Conditions	Yield
In N,N-dimethyl-formamide at 120℃; for 24h;	89%
In N,N-dimethyl-formamide at 120℃; for 24h; Inert atmosphere;	88%

2-Bromo-5-chloro-pyridine (40473-01-6) + methyl 2-(3-amino-4-(isobutyl(tetrahydro-2H-pyran-4-yl)amino)phenyl)-2-methylpropanoate → methyl 2-(3-((5-chloropyridin-2-yl)amino)-4-(isobutyl(tetrahydro-2H-pyran-4-yl)amino)phenyl)-2-methylpropanoate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; Inert atmosphere;	89%

2-Bromo-5-chloro-pyridine (40473-01-6) + methyl [(2S)-3-methyl-1-oxo-1-{(2S)-2-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-benzimidazol-2-yl]pyrrolidin-1-yl}butan-2-yl]carbamate (1228552-50-8) → methyl (S)-1-((S)-2-(5-(5-chloropyridin-2-yl)-1H-benzo[d]imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate (1399843-62-9)

Conditions	Yield
With caesium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 80℃; for 16h; Sealed tube; Inert atmosphere;	88%

2-Bromo-5-chloro-pyridine (40473-01-6) → 5-chloro-2-iodo-pyridine (244221-57-6)

Conditions	Yield
With chloro-trimethyl-silane; sodium iodide In various solvent(s) for 6h; Heating;	87%
Stage #1: 2-Bromo-5-chloro-pyridine With acetyl chloride; sodium iodide In acetonitrile for 3h; Heating / reflux; Stage #2: With potassium carbonate In water; acetonitrile at 0℃;	75%
Stage #1: 2-Bromo-5-chloro-pyridine With acetyl chloride; sodium iodide In acetonitrile for 6h; Heating / reflux; Stage #2: With potassium carbonate In water; acetonitrile at 0℃;	75%
With chloro-trimethyl-silane; sodium iodide In acetonitrile Reflux;

2-Bromo-5-chloro-pyridine (40473-01-6) + tri(p-isopropoxyphenyl)bismuth (95149-18-1) → 5-chloro-2-(4-isopropoxyphenyl)pyridine

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;	87%

2-Bromo-5-chloro-pyridine (40473-01-6) + tris(4-methoxyphenyl)bismuth (33397-21-6) → 5-chloro-2-(4-methoxyphenyl)pyridine

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 2h; Schlenk technique; Inert atmosphere; chemoselective reaction;	86%

2-Bromo-5-chloro-pyridine (40473-01-6) + triethylsilyl chloride (994-30-9) → 2-bromo-5-chloro-4-(triethylsilyl)pyridine

Conditions	Yield
With n-butyllithium; diisopropylamine In tetrahydrofuran; hexane at -20℃; for 1.25h;	86%

2-Bromo-5-chloro-pyridine (40473-01-6) + S-Methylisothiourea sulfate (867-44-7) → 5-chloro-2-(methylsulfanyl)pyridine (89379-91-9)

Conditions	Yield
With caesium carbonate In dimethyl sulfoxide at 80℃; for 5h;	86%

2-Bromo-5-chloro-pyridine (40473-01-6) + N,N-dimethyl acetamide (127-19-5) → 1-(5-chloropyridin-2-yl)ethan-1-one (94952-46-2)

Conditions	Yield
Stage #1: 2-Bromo-5-chloro-pyridine With sec.-butyllithium In diethyl ether; hexane at -60℃; for 2h; Stage #2: N,N-dimethyl acetamide In diethyl ether; hexane for 3h; Stage #3: With hydrogenchloride; water In diethyl ether; hexane	85%
Stage #1: 2-Bromo-5-chloro-pyridine With n-butyllithium In diethyl ether; hexane at -78℃; Stage #2: N,N-dimethyl acetamide In diethyl ether; hexane for 0.5h;	59%
With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h;	59%
Stage #1: 2-Bromo-5-chloro-pyridine With sec.-butyllithium In cyclohexane at -74℃; for 1.66667h; Stage #2: N,N-dimethyl acetamide In diethyl ether; cyclohexane at -74℃; for 1.66667h;

2-Bromo-5-chloro-pyridine (40473-01-6) + 2-Methylphenylboronic acid (16419-60-6) → 5-chloro-2-(o-tolyl)pyridine (1345043-96-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene Reflux;	84%
With Pd-catalyzed Suzuki coupling;

2-Bromo-5-chloro-pyridine (40473-01-6) + N-boc-2-pyrroleboronic acid (135884-31-0) → tert-butyl 2-(5-chloropyridin-2-yl)-1H-pyrrole-1-carboxylate

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water Suzuki Coupling; Inert atmosphere; Reflux;	84%

2-Bromo-5-chloro-pyridine (40473-01-6) + 5-(chloromethyl)-1,3-oxazolidin-2-one (22625-57-6) → 5-(chloromethyl)-3-(5-chloropyridin-2-yl)-1,3-oxazolidin-2-one (1093752-23-8)

Conditions	Yield
With caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium(0) In 1,4-dioxane at 85℃; for 12h;	83%
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 80℃;

2-Bromo-5-chloro-pyridine (40473-01-6) → 5-chloro-pyridin-2-yl hydrazine (27032-63-9)

Conditions	Yield
With hydrazine hydrate In isopropyl alcohol for 10h; Reflux;	82%

2-Bromo-5-chloro-pyridine (40473-01-6) + benzyl (4R)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate (271260-90-3) → (R)-2-(benzyloxycarbonyl)amino-4-(4-chloropyridin-2-yl)-1-butanol (271261-12-2)

Conditions

Yield

Stage #1: benzyl (4R)-2,2-dimethyl-4-vinyl-1,3-oxazolidine-3-carboxylate With 9-borabicyclo[3.3.1]nonane dimer In toluene at 80 - 85℃; hydroboration; Stage #2: 2-Bromo-5-chloro-pyridine With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetra-(n-butyl)ammonium iodide In toluene at 90℃; Suzuki cross-coupling; Stage #3: With hydrogenchloride In methanol for 24h; Ring cleavage; Further stages.;

81%

2-Bromo-5-chloro-pyridine (40473-01-6) + 5-chloroindole 2,3-dione (17630-76-1) → 2,8-dichloro-11H-pyrido[2,1-b]quinazolin-11-one

Conditions	Yield
With copper(II) acetate monohydrate; sodium hydrogencarbonate In N,N-dimethyl-formamide at 120℃; for 10h;	81%

2-Bromo-5-chloro-pyridine (40473-01-6) + 4-{3-[4-(difluoromethoxy)phenyl]-1,2,4-oxadiazol-5-yl}pyrrolidin-2-one → 1-(5-chloropyridin-2-yl)-4-[3-{4-(difluoromethoxy)phenyl}-1,2,4-oxadiazol-5-yl]pyrrolidin-2-one

Conditions	Yield
With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl In toluene at 120℃; for 2h; Inert atmosphere;	81%

Upstream product

• 1072-98-6 5-chloro-2-pyridylamine 
• 4214-79-3 5-chloro-2-pyridinol 
• 16110-09-1 2,5 dichloropyridine 

Downstream Products

• 100846-27-3 5,5'-dichloro-2,2'-bipyridine 
• 271261-12-2 (R)-2-(benzyloxycarbonyl)amino-4-(4-chloropyridin-2-yl)-1-butanol 
• 652148-93-1 5-chloro-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine 
• 652148-91-9 (5-chloropyridin-2-yl)boronic acid 
• 244221-57-6 5-chloro-2-iodo-pyridine 
• 128072-93-5 ethyl 5-chloropyridine-2-carboxylate 
• 27032-65-1 cyclohexanone (5-chloropyridin-2-yl)hydrazone 
• 1072-98-6 5-chloro-2-pyridylamine 
• 1394062-37-3 3-chloro-6-methyl-6,7,8,9-tetrahydro-5H-pyrido-[3',4':4,5]pyrrolo[2,3-b]pyridine 
• 27032-63-9 5-chloro-pyridin-2-yl hydrazine 
• 89379-91-9 5-chloro-2-(methylsulfanyl)pyridine 
• 89809-64-3 2-cyano-5-chloropyridine 

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