223463-13-6

Basic information

• Product Name: 5-Bromo-2-iodopyridine
• Synonyms: 5-BROMO-2-IODOPYRIDINE 97%;5-bromo-2-iodopyridine 97% 5g;5-Bromo-2-iodopyridine, 98+%;2-iodine-5-broMopyridine;5-CroMo-2-iodopyridine;PYRIDINE, 5-BROMO-2-IODO-;5-BROMO-2-IODOPYRIDINE;2-IODO-5-BROMOPYRIDINE
• CAS NO: 223463-13-6
• Molecular Formula: C₅H₃BrIN
• Molecular Weight: 283.89
• EINECS: -0
• Product Categories: Heterocycles;Pyridines derivates;Heterocycle;Bromopyridines;Halopyridines;Iodopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl Iodine|alkyl Iodine;blocks;Bromides;Iodides;Pyridines;Pyridine;pyridine derivative;Pyridine Series;Halides
• Mol File: 223463-13-6.mol
• Article Data: 16

Chemical Properties

• Melting Point: 113-117 °C(lit.)
• Boiling Point: 258.8 °C at 760 mmHg
• Flash Point: 110.3 °C
• Appearance: White to beige/Crystalline Powder
• Density: 2.347 g/cm³
• Vapor Pressure: 0.0218mmHg at 25°C
• Refractive Index: 1.665
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: DMSO, Methanol (Slightly)
• PKA: -0.51±0.10(Predicted)
• Sensitive: Light Sensitive
• Stability: Light Sensitive
• BRN: 2119
• CAS DataBase Reference: 5-Bromo-2-iodopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Bromo-2-iodopyridine(223463-13-6)
• EPA Substance Registry System: 5-Bromo-2-iodopyridine(223463-13-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• HazardClass: IRRITANT, LIGHT SENSITIVE
• Hazardous Substances Data: 223463-13-6(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow Cryst

Uses

5-Bromo-2-iodopyridine may be used in the synthesis of the following:5-bromopyridyl-2-magnesium chloride via reaction with isopropylmagnesium chloride solution5-bromo-2-pyridylzinc iodide via treatment with active zinc in tetrahydrofuran5-bromo-2-(trifluoromethyl)pyridine via halogen/trifluoromethyl displacement reaction(5-bromopyridin-2-yl)zinc(II) chloride via multi-step synthesis5,5′-dibromo-2,2′-bipyridine via multi-step synthesis

InChI:InChI=1/C5H3BrIN/c6-4-1-2-5(7)8-3-4/h1-3H

Synthetic route

2,5-dibromopyridine (624-28-2) → 2-iodo-5-bromopyridine (223463-13-6)

Conditions	Yield
With hydrogen iodide at 100 - 170℃; for 20h;	95%
With hydrogen iodide; potassium iodide for 72h; Reflux;	90%
With chloro-trimethyl-silane; sodium iodide In various solvent(s) for 125h; Heating;	87%

5-bromo-2-iodopyridine N-oxide → 2-iodo-5-bromopyridine (223463-13-6)

Conditions	Yield
With phosphorus trichloride In dichloromethane for 1h; Reflux;	75%

5-bromo-2-pyridylamine (1072-97-5) → 2-iodo-5-bromopyridine (223463-13-6)

Conditions	Yield
With N-iodo-succinimide; sodium nitrite In N,N-dimethyl-formamide at 20℃; for 4h;	72%
With acetic acid; potassium iodide; sodium nitrite

2,5-dibromopyridine (624-28-2) → 2-bromo-5-iodo-pyridine (73290-22-9) + 2,5-di-iodopyridine (116195-81-4) + 2-iodo-5-bromopyridine (223463-13-6)

Conditions	Yield
Stage #1: 2,5-dibromopyridine With nBu4ZnLi2*TMEDA In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene for 18h; Inert atmosphere;	A 41 %Spectr. B 13 %Spectr. C 23 %Spectr.

2,5-dibromopyridine (624-28-2) → 2-bromo-5-iodo-pyridine (73290-22-9) + 2-iodo-5-bromopyridine (223463-13-6)

Conditions	Yield
Stage #1: 2,5-dibromopyridine With nBu4ZnLi2 In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene for 18h; Inert atmosphere;	A 8 %Spectr. B 80 %Spectr.

2-amino-5-bromopyridine 1-oxide (696-15-1) → 2-iodo-5-bromopyridine (223463-13-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: toluene-4-sulfonic acid; potassium iodide; sodium nitrite / water / 3 h / 20 °C 2: phosphorus trichloride / dichloromethane / 1 h / Reflux View Scheme

2-iodo-5-bromopyridine (223463-13-6) + 3-Aminophenylboronic acid (30418-59-8) → 3-(5-bromopyridin-2-yl)aniline (1191616-42-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Sealed tube;	100%

2-iodo-5-bromopyridine (223463-13-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 5-bromo-pyridine-2-carbaldehyde (31181-90-5)

Conditions	Yield
Stage #1: 2-iodo-5-bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at -15 - -5℃; for 1h; Stage #2: N,N-dimethyl-formamide In tetrahydrofuran at -5 - 25℃; for 1.5h;	99%
With isopropylmagnesium chloride In tetrahydrofuran at -10℃;	94%
Stage #1: 2-iodo-5-bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at -15 - 0℃; for 1h; Stage #2: N,N-dimethyl-formamide In dichloromethane at 0 - 20℃; for 1.5h; Stage #3: With hydrogenchloride In tetrahydrofuran for 0.5h; below 25 deg C;	90%

2-iodo-5-bromopyridine (223463-13-6) + phenylboronic acid (98-80-6) → 5-bromo-2-phenylpyridine (27012-25-5)

Conditions	Yield
With potassium carbonate In 1,2-dimethoxyethane at 100℃; for 24h; Suzuki Coupling;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 2h; Inert atmosphere; Reflux;	95%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; water; benzene for 2h; Reflux;	94.43%

2-iodo-5-bromopyridine (223463-13-6) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → 4-(5-bromopyridin-2-yl)-N,N-diphenylaniline (1257900-36-9)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 80℃; for 19h; Inert atmosphere;	98%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 80℃; for 20.5h; Inert atmosphere;	98%

2-iodo-5-bromopyridine (223463-13-6) + C77H118N2O24 → C97H126Br4N6O24

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In toluene at 20℃; for 12h; Inert atmosphere;	98%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 2-iodo-5-bromopyridine (223463-13-6) → methyl 5-bromopicolinate (29682-15-3)

Conditions	Yield
With TEA; bis-triphenylphosphine-palladium(II) chloride at 60℃; under 3102.97 Torr; for 15h;	97%

2-iodo-5-bromopyridine (223463-13-6) + trimethyltin(IV)chloride (1066-45-1) → 5-bromo-2-(trimethylstannyl)pyridine (198985-48-7)

Conditions	Yield
With C4H9Li In hexane; toluene addn. of hexane soln. of butyllithium to toluene soln. of pyridine deriv. at -20°C, stirring at -78°C for 2 h, addn. of toluene soln. of tin compd., stirring for 1 h at -78°C, warming to room temp.; evapn., extn. (CH2Cl2), filtration, evapn., chromy. (alumina, diethyl ether), NMR and MS;	97%
With CH3CH2CH2CH2Li In toluene treatment of pyridine deriv. with butyllithium at -20.degre.C in toluene, cooing to -78°C, treatment with tin compd., warming to room temp.;	86%
Stage #1: 2-iodo-5-bromopyridine With n-butyllithium In hexane; toluene at -40 - -30℃; for 0.5h; Stage #2: trimethyltin(IV)chloride In hexane; toluene at -78℃; for 1h;	75%

2-iodo-5-bromopyridine (223463-13-6) + diethyl malonate (105-53-3) → diethyl 2-(5-bromopyridin-2-yl)malonate (1215098-80-8)

Conditions	Yield
With 2-Picolinic acid; copper(l) iodide; caesium carbonate In 1,4-dioxane at 70℃;	97%
With 2-Picolinic acid; copper(l) iodide; caesium carbonate In 1,4-dioxane at 70℃; for 24h; Inert atmosphere;	50%
With 2-Picolinic acid; copper(l) iodide; caesium carbonate In 1,4-dioxane at 80℃; for 16h;

2-iodo-5-bromopyridine (223463-13-6) + 4-methoxyphenylboronic acid (5720-07-0) → 5-bromo-2-(4-methyloxyphenyl)pyridine (88345-93-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In water; toluene at 80℃; for 40.5h; Inert atmosphere;	97%
Stage #1: 2-iodo-5-bromopyridine; 4-methoxyphenylboronic acid With sodium carbonate In 1,4-dioxane; water for 0.5h; Suzuki Coupling; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 80 - 110℃; Inert atmosphere;	52%

2-iodo-5-bromopyridine (223463-13-6) + 1-phenyl-2-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole (1572938-37-4) → 2-(5-bromo-[2,3’-bipyridin]-6’-yl)-1-phenyl-1H-benzo[d]imidazole

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; for 20h; Inert atmosphere;	97%

2-iodo-5-bromopyridine (223463-13-6) + N,N-diphenyl-4’-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1’-biphenyl]-4-amine (675571-82-1) → 4’-(5-bromopyridin-2-yl)-N,N-diphenyl-[1,1‘-biphenyl]-4-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 95℃; for 24h; Inert atmosphere;	97%

iodotrifluoromethane (2314-97-8) + 2-iodo-5-bromopyridine (223463-13-6) + zinc (7440-66-6) → 5-bromo-2(trifluoromethyl)pyridine (436799-32-5)

Conditions	Yield
Stage #1: iodotrifluoromethane; zinc With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone at 20℃; for 2h; Inert atmosphere; Stage #2: 2-iodo-5-bromopyridine With copper(l) iodide at 50℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; chemoselective reaction;	96%

2-iodo-5-bromopyridine (223463-13-6) + 3-methyl-N-(quinolin-8-yl)thiophene-2-carboxamide → 3-((5-bromopyridin-2-yl)methyl)-N-(quinolin-8-yl)thiophene-2-carboxamide

Conditions	Yield
With silver(I) acetate; palladium diacetate In toluene at 110℃; for 12h; Inert atmosphere;	96%

2-iodo-5-bromopyridine (223463-13-6) + 3,6-di(N-carbazolyl)carbazole (606129-90-2) → C41H25BrN4

Conditions	Yield
With copper(l) iodide; potassium carbonate In chlorobenzene at 120℃; Inert atmosphere;	96%

2-iodo-5-bromopyridine (223463-13-6) → 3-bromo-6-deuteriopyridine

Conditions	Yield
Stage #1: 2-iodo-5-bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 0.75h; Stage #2: With d(4)-methanol In tetrahydrofuran at 20℃; for 0.25h;	95%
Stage #1: 2-iodo-5-bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: With d(4)-methanol In tetrahydrofuran at 20℃; for 0.5h;	37.7%

2-iodo-5-bromopyridine (223463-13-6) + pyridin-2-ylzinc(II) bromide → 5-bromo-2,2'-bipyridyl (15862-19-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 75℃; for 18h;	95%
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h;	89%
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; Inert atmosphere;	83%

2-iodo-5-bromopyridine (223463-13-6) + 2-pyridyl fluoroiodomethyl sulfone (1415115-02-4) → C11H8BrFN2O2S (1415115-23-9)

Conditions	Yield
Stage #1: 2-pyridyl fluoroiodomethyl sulfone With diethylzinc In hexane; N,N-dimethyl-formamide at -30 - -25℃; for 0.0833333h; Inert atmosphere; Stage #2: With copper(l) iodide In hexane; N,N-dimethyl-formamide at -15℃; for 0.25h; Inert atmosphere; Stage #3: 2-iodo-5-bromopyridine In hexane; N,N-dimethyl-formamide at 20℃; for 8h; Solvent; Temperature; Inert atmosphere;	95%

2-iodo-5-bromopyridine (223463-13-6) + phenylboronic acid (98-80-6) → 2,5-diphenylpyridine (15827-72-2)

Conditions	Yield
With potassium carbonate In water at 50℃; for 2.5h; Suzuki Coupling;	95%
With magnesium hydroxide; potassium hydroxide; barium(II) hydroxide; calcium hydroxide In water at 20℃; for 2.5h; Suzuki Coupling;	95%
With 0.1 % Cu/C; potassium carbonate In water at 50℃; for 3.5h; Suzuki Coupling; Green chemistry;	92%

benzoimidazole (51-17-2) + 2-iodo-5-bromopyridine (223463-13-6) → 1-(6-iodopyridin-3-yl)-1H-benzo[d]imidazole

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 14h; Ullmann Condensation;	95%

NH-pyrazole (288-13-1) + 2-iodo-5-bromopyridine (223463-13-6) → C8H6IN3

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 110℃; for 14h; Ullmann Condensation;	95%

1-methyl-2-benzimidazolone (1849-01-0) + 2-iodo-5-bromopyridine (223463-13-6) → 1-(5-bromopyridin-2-yl)-3-methyl-1H-benzo[d]midazol-2(3H)-one (1043906-09-7)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	94%

iodobenzene (591-50-4) + 2-iodo-5-bromopyridine (223463-13-6) → 5-bromo-2-phenylpyridine (27012-25-5)

Conditions	Yield
Stage #1: 2-iodo-5-bromopyridine With zinc In tetrahydrofuran at 0 - 20℃; Negishi coupling reaction; Inert atmosphere; Stage #2: iodobenzene With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 24h; Negishi coupling reaction; Inert atmosphere; chemoselective reaction;	94%

carbon monoxide (201230-82-2) + 2-iodo-5-bromopyridine (223463-13-6) + benzyl alcohol (100-51-6) → 5-bromopyridine-2-carboxylic acid benzyl ester (188052-14-4)

Conditions	Yield
With TEA; bis-triphenylphosphine-palladium(II) chloride at 60℃; under 3102.97 Torr; for 15h;	93%

2-iodo-5-bromopyridine (223463-13-6) + 3,6-bis(3,6-di-tert-butylcarbazol-N-yl)carbazole (551951-04-3) → C57H57BrN4

Conditions	Yield
With copper(l) iodide; potassium carbonate In chlorobenzene at 120℃; for 24h; Inert atmosphere;	92%

4-Trifluoromethoxyphenol (828-27-3) + 2-iodo-5-bromopyridine (223463-13-6) → 5-bromo-2-({4-[(trifluoromethyl)oxy]phenyl}oxy)pyridine (909849-01-0)

Conditions	Yield
With 2-Picolinic acid; potassium phosphate; copper(l) iodide In dimethyl sulfoxide at 80℃; for 18h;	91%

N,N-dimethyl acetamide (127-19-5) + 2-iodo-5-bromopyridine (223463-13-6) → 1-(5-bromopyridin-2-yl)ethanone (214701-49-2)

Conditions	Yield
Stage #1: 2-iodo-5-bromopyridine With n-butyllithium In hexane; toluene at -40℃; for 1h; Stage #2: N,N-dimethyl acetamide In hexane; toluene at -40 - 20℃; for 1h;	91%

benzoimidazole (51-17-2) + 2-iodo-5-bromopyridine (223463-13-6) → 1-(5-bromopyridin-2-yl)-1H-benzo[d]imidazole (1043906-08-6)

Conditions	Yield
With copper(l) iodide; 1,10-Phenanthroline; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;	90%

2-iodo-5-bromopyridine (223463-13-6) + (S)-2-(aminomethyl)pyrrolidine-1-carboxylic acid tert-butyl ester (119020-01-8) → C15H22BrN3O2 (475106-13-9)

Conditions	Yield
With 2-(2-methyl-1-oxopropyl)cyclohexanone; caesium carbonate; copper(l) iodide for 20h; Inert atmosphere;	90%

2-iodo-5-bromopyridine (223463-13-6) + 7,7-diphenyl-5,7-dihydroindeno[2,1-b]carbazole → C36H23BrN2

Conditions	Yield
With potassium phosphate; copper(l) iodide; ethylenediamine In toluene at 135℃; for 5h;	90%

Upstream product

• 624-28-2 2,5-dibromopyridine 
• 696-15-1 2-amino-5-bromopyridine N-oxide 
• 1072-97-5 5-bromo-2-pyridylamine 

Downstream Products

• 29682-15-3 methyl 5-bromopicolinate 
• 188052-14-4 5-bromopyridine-2-carboxylic acid benzyl ester 
• 206357-52-0 (5-bromopyridin-2-yl)(phenyl)methanone 
• 364794-78-5 5-bromo-2-(1-piperidinylmethyl)pyridine 
• 291312-74-8 2-trimethylsilyl-5-bromopyridine 
• 97483-77-7 2-Cyano-5-bromopyridine 
• 823806-43-5 (+/-)-1-(5-bromopyridin-2-yl)butan-1-ol 
• 31181-90-5 5-bromo-pyridine-2-carbaldehyde 
• 19520-27-5 5-bromo-2-(phenylthio)pyridine 
• 880266-33-1 4-(5-bromopyridine-2-ylethynyl)benzonitrile 
• 774-53-8 5-bromo-2,3′-bipyridine 
• 557793-46-1 2-(benzo[b]thiophen-2-yl)-5-bromopyridine 
• 111770-81-1 5-bromo-2-(hex-1-yn-1-yl)pyridine 
• 870761-78-7 tert-butyl 3-[(5-bromopyridin-2-yl)carbonyl]azetidine-1-carboxylate 

Relevant articles and documents

Improved synthesis of 5,5"-dibromo-2,2′:6′,2"-terpyridine

5,5"-dibromo-2,2′:6′,2"-terpyridine has been synthesized in very good yield and on a multigram scale modifying the Stille cross-coupling strategy published by Schlüter and coworkers in a previous work.

A New, Simple, and General Synthesis of N -Oxides of Iodopyridines and Iodoquinolines via the Diazotization-Iodination of Heterocyclic Amino N -Oxides in the Presence of p -Toluenesulfonic Acid in Water

The diazotization of a series of N -oxides of aminopyridines and aminoquinolines under the action of sodium nitrite in the presence of KI and p -TsOH in water at room temperature leads to the formation of the corresponding N -oxides of iodopyridines and iodoquinolines in high yields. The method has a general character and can be used for the preparation of 3-, 2-, and 4- N -oxides of iodopyridines.

Hybrid charged heterometallic Pt-Ir complexes: Tailoring excited states by taking the best of both worlds

The CC-linkage of Pt(PR3)2(CCAr)2 with (CN)2Ir(NN)+ (CN = 2-phenylpyridine; NN = bipyridyl) leads to hetero-bi- and trimetallic species exhibiting photophysical properties reminiscent of both [Pt]- and [Ir]-containing moieties through the generation of a [Pt] → [Ir] charge transfer excited state. The Royal Society of Chemistry 2012.