109-04-6

Basic information

• Product Name: 2-Bromopyridine
• Synonyms: TIMTEC-BB SBB003999;AKOS BBS-00004324;ALPHA-BROMOPYRIDINE;BROMOPYRIDINE(2-);2-BROMO PYRIDINE 2-BROMO PYRIDINE;2-Bromopyridine ,99%;2-Bromopyridine;2-broMide pyridine
• CAS NO: 109-04-6
• Molecular Formula: C₅H₄BrN
• Molecular Weight: 158
• EINECS: 203-641-6
• Product Categories: Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Halides;Pyridines;Pyridines derivates;Bromopyridines;Halopyridines;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;alkyl bromide
• Mol File: 109-04-6.mol
• Article Data: 49

Chemical Properties

• Melting Point: 193°C
• Boiling Point: 192-194 °C(lit.)
• Flash Point: 130 °F
• Appearance: Clear colorless to pale brown/Liquid
• Density: 1.657 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.784mmHg at 25°C
• Refractive Index: n20/D 1.572(lit.)
• Storage Temp.: Refrigerator
• Solubility: 20g/l
• PKA: pK1: 0.71(+1) (25°C)
• Water Solubility: Slightly miscible with water.
• Stability: Stable. Flammable. Incompatible with strong oxidizing agents, strong acids, acid chlorides.
• BRN: 105789
• CAS DataBase Reference: 2-Bromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Bromopyridine(109-04-6)
• EPA Substance Registry System: 2-Bromopyridine(109-04-6)

Safety Data

• Hazard Codes: T,Xn,F
• Statements: 10-24/25-36/37/38-23/24/25-20/21/22
• Safety Statements: 16-36/37-45-38-36/37/39-28A-26
• RIDADR: UN 2929 6.1/PG 2
• WGK Germany: 3
• RTECS: US3850000
• F: 8
• TSCA: Yes
• HazardClass: 6.1
• PackingGroup: II
• Hazardous Substances Data: 109-04-6(Hazardous Substances Data)

Usage

Chemical Description

2-bromopyridine is a halogenated pyridine compound.

Chemical Properties

light yellow oily or dark red liquid. miscible with ethanol, ether, benzene and pyridine, still soluble in water.

Uses

2-Bromopyridine is a 2-halogenated pyridine used in the preparation of a variety of biologically active compounds such as antimalarial agents and beta-adrenoceptor agonist.

Application

2-Bromopyridine can be used as:A building block in the formation of C?N bond by various cross coupling reactions.A reactant in Negishi cross-coupling reaction with aryl halides catalyzed by palladium.A reactant in the synthesis of 2′-pyridyldifluoroacetate with ethyl bromodifluoroacetate in presence of copper as a catalyst.

Preparation

2-Bromopyridine is synthesized from 2-aminopyridine by bromination. In industrial production, hydrobromic acid (over 48%) is first cooled to below 0°C, 2-aminopyridine is slowly added, and then liquid bromine is added dropwise in a salt bath under freezing, and the rate of addition is to control the reaction temperature below -5°C appropriate. After adding, add sodium nitrite aqueous solution dropwise, control the reaction temperature to be below 0°C, stir for 20-30min, dropwise add 50% sodium hydroxide solution, extract the reaction solution with ether, wash with water, dry with anhydrous sodium sulfate, filter, and recover Diethyl ether, the residue was distilled under reduced pressure, and the 88°C-94°C/3333Pa fraction was collected to obtain the finished product of 2-bromopyridine with a yield of 83.8%.

Reactions

2-Bromopyridine reacts with butyllithium to give 2-lithiopyridine, which is a versatile reagent.Pyrithione can be prepared in a two-step synthesis from 2-bromopyridine by oxidation to the N-oxide with a suitable peracid followed by substitution using either sodium dithionite or sodium sulfide with sodium hydroxide to introduce the thiol functional group.

Flammability and Explosibility

Flammable

Purification Methods

Dry 2-bromopyridine over KOH for several days, then distil it from CaO under reduced pressure, and taking the middle fraction. [Beilstein 20/5 V 422.]

InChI:InChI=1/C5H4BrN/c6-5-3-1-2-4-7-5/h1-4H

Synthetic route

2,6-Dibromopyridine (626-05-1) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With n-butyllithium; butyl magnesium bromide In toluene at -10℃;	100%
With n-butyllithium; isopropyl alcohol In hexane; dichloromethane 1.) -78 deg C, 1 h, 2.) -78 deg C, 30, min; warm to room temperature;	90%
With n-butyllithium; formaldehyd In tetrahydrofuran at -70 - -40℃;	90%

2-bromopyridine 1-oxide hydrochloride (80866-91-7) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With titanium In tetrahydrofuran for 0.25h; Ambient temperature;	97%

2-bromopyridine-N-oxide (14305-17-0) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With Dimethylphenylsilane In tetrahydrofuran at 20℃; for 24h; Inert atmosphere;	96%
With triphenylphosphine; [MoO2Cl2(dmf)2] In tetrahydrofuran for 5h; Heating;	87%
With hydrogen; triethyl phosphite In isopropyl alcohol at 100℃; under 4500.45 Torr; for 12h; Glovebox; chemoselective reaction;	87%

2-aminopyridine (504-29-0) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With 2-methylphenyl bromide; copper(I) bromide In cyclohexane at 5 - 45℃; for 3.41667h; Concentration; Temperature;	91%
	78%
With hydrogen bromide; bromine; sodium nitrite In water at -2℃; for 0.333333h;	65%

Pyridin-Palladium(II)-chlorid-Komplex → 2-bromo-pyridine (109-04-6) + 3-Bromopyridine (626-55-1)

Conditions	Yield
With bromine In cyclohexane at 0 - 5℃; for 1h;	A 86% B 10%
With bromine In cyclohexane at 75℃; for 1h;	A 32% B 66%

2-hydroxypyridin (142-08-5) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With tetrabutylammomium bromide; phosphorus pentoxide In 1,2-dichloro-benzene at 180℃; for 10h;	75%
With N-Bromosuccinimide; triphenylphosphine In 1,4-dioxane for 4h; Bromination; substitution; Heating;	54%
With carbon tetrabromide; triphenylphosphine In toluene for 8h; Reflux;	100 %Chromat.

pyridine (110-86-1) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With n-butyllithium; 2-(N,N-dimethylamino)ethanol; carbon tetrabromide 1.) hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h;	72%

2,5-dibromopyridine (624-28-2) + pentan-3-one (96-22-0) → 2-bromo-pyridine (109-04-6) + 2-(3-hydroxy-pentane-3-yl)-5-bromo-pyridine (874915-22-7) + 2-bromo-5-(3-hydroxy-pentane-3-yl)pyridine (874915-24-9) + 3-ethylheptan-3-ol (19780-41-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 5℃; for 0.0833333h;	A 8.7% B 11% C 68.8% D 3.9%

2,5-dibromopyridine (624-28-2) + pentan-3-one (96-22-0) → 2-bromo-pyridine (109-04-6) + 2-(3-hydroxy-pentane-3-yl)-5-bromo-pyridine (874915-22-7) + 2-bromo-5-(3-hydroxy-pentane-3-yl)pyridine (874915-24-9) + 2,5-di(3-hydroxy-pentane-3-yl)pyridine (874915-27-2) + 3-ethylheptan-3-ol (19780-41-7)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at 5℃; for 0.1h;	A 2.8% B 1.9% C 60.7% D 2.4% E 4.8%

pyridine (110-86-1) + acetyl hypofluorite (78948-09-1) → 2-bromo-pyridine (109-04-6) + 2-acetoxypyridine (3847-19-6)

Conditions	Yield
With 1,2-dibromomethane Ambient temperature;	A 60% B 20%

2-Pyridone (142-08-5) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With N-Bromosuccinimide; triphenylphosphine In 1,4-dioxane for 4h; Heating;	54%

2-chloropyridine (109-09-1) → 2-bromo-pyridine (109-04-6)

Conditions	Yield
With trimethylsilyl bromide In various solvent(s) for 100h; Heating;	49%

[EtAl(6-Br-2-py)3Li] + water (7732-18-5) → 2-bromo-pyridine (109-04-6) + [EtAl(OH)(6-Br-2-py)2Li]2

Conditions	Yield
In toluene at 20℃; for 3h; Inert atmosphere; Schlenk technique;	A n/a B 43%

pyridine (110-86-1) + benzyl bromide (100-39-0) → 2-bromo-pyridine (109-04-6) + 2-Benzylpyridine (101-82-6)

Conditions	Yield
With copper(l) iodide; n-butyllithium; 2-(N,N-dimethylamino)ethanol 1.) hexane, -78 deg C, 1 h, 2.) THF, -78 deg C, 1 h;	A 45 % Chromat. B 25%

methanol (67-56-1) + [EtAl(6-Br-2-py)3Li] + toluene (108-88-3) → 2-bromo-pyridine (109-04-6) + [EtAl(OMe)(6-Br-2-py)2Li]2*toluene

Conditions	Yield
at 0 - 20℃; for 2.5h; Inert atmosphere; Glovebox;	A n/a B 22%

pyridine (110-86-1) → 2-bromo-pyridine (109-04-6) + 2,6-Dibromopyridine (626-05-1)

Conditions	Yield
With bromine at 500℃; Leiten ueber Bimsstein;
With bromine at 500℃; Leiten ueber Glas;

2,6-Dibromopyridine (626-05-1) → pyridine (110-86-1) + 2-bromo-pyridine (109-04-6)

Conditions	Yield
With methanol; n-butyllithium 1.) THF, -89 deg C, 4.5 h, 2.) THF, from -90 deg C to RT, 6 h; Multistep reaction;

3-bromo-2-chloropyridine (52200-48-3) + n-butyllithium (109-72-8, 29786-93-4) → 2-chloropyridine (109-09-1) + 2-bromo-pyridine (109-04-6) + bromo-4 chloro-2 deuterio-3 pyridine (100921-62-8) + chloro-2 butyl-3 pyridine (73583-36-5) + chloro-2 deuterio-3 pyridine (100921-61-7) + chloro-2 butyl-4 pyridine (100921-63-9)

Conditions	Yield
With ethyl [2]alcohol Product distribution; Mechanism; 1) THF, -40 deg C, 10 min, 2) THF, -40 deg C, 15 min; a new "homotransmetalation" reaction, further reagents and conditions;

3-bromo-2-chloropyridine (52200-48-3) + n-butyllithium (109-72-8, 29786-93-4) → 2-chloropyridine (109-09-1) + 2-bromo-pyridine (109-04-6) + bromo-4 chloro-2 deuterio-3 pyridine (100921-62-8) + chloro-2 bromo-4 butyl-3 pyridine (73589-41-0)

Conditions	Yield
With ethyl [2]alcohol 1) THF, -40 deg C, 15 min, 2) THF, -40 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

3-bromo-2-chloropyridine (52200-48-3) + n-butyllithium (109-72-8, 29786-93-4) → 2-bromo-pyridine (109-04-6) + bromo-4 chloro-2 deuterio-3 pyridine (100921-62-8) + chloro-2 butyl-3 pyridine (73583-36-5) + chloro-2 butyl-4 pyridine (100921-63-9)

Conditions	Yield
With ethyl [2]alcohol 1) THF, -40 deg C, 10 min, 2) THF, -40 deg C, 15 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

3-bromo-2-chloropyridine (52200-48-3) → 2-chloropyridine (109-09-1) + 2-bromo-pyridine (109-04-6) + bromo-4 chloro-2 deuterio-3 pyridine (100921-62-8) + chloro-2 bromo-4 butyl-3 pyridine (73589-41-0)

Conditions	Yield
With n-butyllithium; ethyl [2]alcohol 1) THF, -40 deg C, 15 min, 2) THF, -40 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

3-bromo-2-chloropyridine (52200-48-3) → 2-bromo-pyridine (109-04-6) + bromo-4 chloro-2 deuterio-3 pyridine (100921-62-8) + chloro-2 butyl-3 pyridine (73583-36-5) + chloro-2 butyl-4 pyridine (100921-63-9)

Conditions	Yield
With n-butyllithium; ethyl [2]alcohol 1) THF, -40 deg C, 10 min, 2) THF, -40 deg C, 15 min; Yield given. Multistep reaction. Further byproducts given. Yields of byproduct given;

1-bromo-butane (109-65-9) + 2,3-dibromopyridine (13534-89-9) → 2-bromo-pyridine (109-04-6) + bromo-2 butyl-3 pyridine (100921-66-2)

Conditions	Yield
1) THF, -60 deg C, 15 min, 2) THF, -60 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

1-bromo-butane (109-65-9) + 2,3-dibromopyridine (13534-89-9) → 2-bromo-pyridine (109-04-6) + dibromo-2,3 butyl-4 pyridine (100921-68-4) + dibromo-2,4 butyl-3 pyridine (100921-67-3)

Conditions	Yield
1) THF, -60 to -40 deg C, 10 min, 2) THF, -60 deg C, 1 h; Yield given. Multistep reaction. Yields of byproduct given;

2,3-dibromopyridine (13534-89-9) + n-butyllithium (109-72-8, 29786-93-4) → 2-bromo-pyridine (109-04-6) + bromo-2 deuterio-3 pyridine (54267-61-7) + bromo-2 butyl-4 pyridine (100933-54-8) + dibromo-2,4 deuterio-3 pyridine (100921-65-1)

Conditions	Yield
With ethyl [2]alcohol Product distribution; Mechanism; 1) THF, -40 deg C, 10 min, 2) THF, -40 deg C, 15 min; a new "homotransmetalation" reaction, further reagents and conditions;
With ethyl [2]alcohol 1) THF, -40 deg C, 10 min, 2) THF, -40 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

2,3-dibromopyridine (13534-89-9) + pentan-3-one (96-22-0) → 2-bromo-pyridine (109-04-6) + bromo-2 (ethyl-1 hydroxy-1 propyl)-3 pyridine (73583-40-1)

Conditions	Yield
With n-butyllithium 1) THF, -60 deg C, 15 min, 2) THF, -60 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

2,3-dibromopyridine (13534-89-9) + pentan-3-one (96-22-0) → 2-bromo-pyridine (109-04-6) + dibromo-2,3 (ethyl-1 hydroxy-1 propyl)-4 pyridine (100921-64-0)

Conditions	Yield
With n-butyllithium 1) THF, -60 to -40 deg C, 20 min, 2) THF, -60 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

2,3-dibromopyridine (13534-89-9) → 2-bromo-pyridine (109-04-6) + 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
With n-butyllithium; pentan-3-one 1) THF, -40 deg C, 15 min, 2) THF, -60 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

2,3-dibromopyridine (13534-89-9) → 2-bromo-pyridine (109-04-6) + bromo-2 deuterio-3 pyridine (54267-61-7) + dibromo-2,4 deuterio-3 pyridine (100921-65-1)

Conditions	Yield
With n-butyllithium; ethyl [2]alcohol 1) THF, -40 deg C, 15 min, 2) THF, -40 deg C, 15 min; Yield given. Multistep reaction. Yields of byproduct given;

2-bromo-pyridine (109-04-6) + phenol (108-95-2) → 2-phenoxypyridine (4783-68-0)

Conditions	Yield
With copper; caesium carbonate In N,N-dimethyl-formamide at 100℃; for 0.166667h; Ullmann Condensation; Microwave irradiation; Inert atmosphere;	100%
With 1,1,1,5,5,5-hexafluoroacetylacetone; copper(II) ferrite; caesium carbonate In 1-methyl-pyrrolidin-2-one at 135℃; for 24h; Ullmann Condensation; Inert atmosphere; Schlenk technique;	99%
With 2-acetonylpyridine; caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 90℃; for 15h; Inert atmosphere; chemoselective reaction;	98%

2-bromo-pyridine (109-04-6) → 2-aminopyridine (504-29-0)

Conditions	Yield
With [Cu2(2,7-bis(pyridin-2-yl)-l,8-naphthyridine)(OH)(CF3COO)3]; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 120℃; for 16h; Sealed tube;	100%
With ammonia; triethylamine In water at 20℃; for 4.25h;	97%
With ammonium hydroxide at 20℃; for 7h; Catalytic behavior;	96%

2-bromo-pyridine (109-04-6) → pyrid-2-ylhydrazine (4930-98-7)

Conditions	Yield
With hydrazine at 100℃; for 2h; Substitution;	100%
With hydrazine hydrate In ethanol; water	58%
With hydrazine hydrate for 4h; Heating;	54%

2-bromo-pyridine (109-04-6) → [2,2]bipyridinyl (366-18-7)

Conditions	Yield
With palladium diacetate; potassium carbonate In water; N,N-dimethyl-formamide at 210℃; for 24h; Catalytic behavior; Solvent; Reagent/catalyst;	100%
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; cesium fluoride In dimethyl sulfoxide at 120℃; for 8h;	96%
With bis(triphenylphosphine)nickel(II) chloride; sodium hydride; triphenylphosphine; zinc In toluene at 70 - 90℃; Ullmann-type coupling;	93%

2-pyrrolidinon (616-45-5) + 2-bromo-pyridine (109-04-6) → 2-oxo-1-(2-pyridyl)-tetrahydropyrrole (91596-63-3)

Conditions	Yield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In toluene for 24h; Inert atmosphere; Reflux;	100%
With caesium carbonate; copper(I) bromide In dimethyl sulfoxide at 60℃; for 22h;	95%
With dimethylenecyclourethane; copper(l) iodide; sodium methylate In dimethyl sulfoxide at 120℃; for 24h;	89%
With sodium hydride In N,N-dimethyl-formamide at 130℃; for 0.5h; microwave irradiation;	65%
With potassium acetate; CuO/SiO2 In xylene for 18h; Heating;	49%

2-bromo-pyridine (109-04-6) + N-Methylformamide (123-39-7) → 2-(N-methylamino)pyridine (4597-87-9)

Conditions	Yield
With potassium hydroxide	100%

2-bromo-pyridine (109-04-6) + 2-Methylphenylboronic acid (16419-60-6) → 2-(2-methylphenyl)pyridine (10273-89-9)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In water; N,N-dimethyl-formamide at 120℃; for 12h; Suzuki Coupling; Inert atmosphere;	96%
With potassium phosphate tribasic heptahydrate; palladium diacetate In ethylene glycol at 80℃; for 1h; Suzuki coupling;	94%

2-bromo-pyridine (109-04-6) + 2-methoxyphenylmagnesium bromide (16750-63-3) → 2-(2-methoxy-phenyl)-pyridine (5957-89-1)

Conditions	Yield
With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 0 - 20℃;	100%
With tetrakis(triphenylphosphine) palladium(0) In toluene at 50 - 100℃; for 1h;	89%
(1,2-bis(diphenylphosphanyl)ethane)dichloridopalladium(II) In tetrahydrofuran for 12h; Ambient temperature;	87%
With bis(acetylacetonate)nickel(II); 1,2-bis-(diphenylphosphino)ethane In tetrahydrofuran at 20℃; for 18h; Corriu-Kumada-Tamao coupling;	80%
With nickel catalyst Inert atmosphere;

2-bromo-pyridine (109-04-6) + N,N-dimethyl-formamide (68-12-2, 33513-42-7) → 2-(Dimethylamino)pyridine (5683-33-0)

Conditions	Yield
With potassium hydroxide	100%
at 130℃; for 12h;	92%
With potassium hydroxide In neat (no solvent) at 100℃; for 24h; Sealed tube;	41%

2-bromo-pyridine (109-04-6) + phenylacetylene (536-74-3) → 2-(2-phenylethynyl)pyridine (13141-42-9)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine In toluene at 60℃; for 16h; Sonogashira coupling;	100%
With potassium carbonate; triphenylphosphine; silver(I) iodide In N,N-dimethyl-formamide at 100℃; for 8h; Sonogashira coupling reaction;	99%
With tetrabutylammomium bromide; potassium acetate; cyclopalladated ferrocenylimine In N,N-dimethyl acetamide at 80℃; for 20h; Sonogashira coupling;	99%

2-bromo-pyridine (109-04-6) + trimethylsilylacetylene (1066-54-2) → 2-(trimethylsilylethynyl)pyridine (86521-05-3)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 70℃; for 3h;	100%
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); triethylamine at 20℃;	97%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine at 50℃; Sonogashira Cross-Coupling; Inert atmosphere;	97%

2-bromo-pyridine (109-04-6) + phenylboronic acid (98-80-6) → 2-phenylpyridine (1008-89-5)

Conditions	Yield
With [Pd(N-(naphthyl)-salicylaldimine(-2H))(triphenylphosphine)]; sodium hydroxide at 120℃; for 24h; Reagent/catalyst; Suzuki Coupling;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
With potassium phosphate; (PdCl2)(2-pyridyl)-6-isopropyl cis piperidine complex In water; N,N-dimethyl-formamide at 110℃; for 2h;	99%

2-bromo-pyridine (109-04-6) + 1-Pentyne (627-19-0) → 2-(pent-1'-ynyl)-pyridine (202828-84-0)

Conditions	Yield
With copper(l) iodide; triphenylphosphine; bis-triphenylphosphine-palladium(II) chloride In triethylamine at 25℃; for 16h; Sonogashira coupling;	100%
Stage #1: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 25℃; for 0.5h; Inert atmosphere; Stage #2: 1-Pentyne at 25℃; for 16h; Inert atmosphere;	94%
Stage #1: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine at 25℃; for 0.5h; Inert atmosphere; Stage #2: 1-Pentyne at 25℃; for 16h; Inert atmosphere;	94%
With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide In diethylamine for 20h; Ambient temperature;	84%
Stage #1: 2-bromo-pyridine With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; triphenylphosphine for 0.5h; Sonogashira Cross-Coupling; Inert atmosphere; Stage #2: 1-Pentyne for 18h; Sonogashira Cross-Coupling; Inert atmosphere; Darkness;	78%

2-bromo-pyridine (109-04-6) + 1,1-dimethoxy-1-(4-bromophenyl)methane (24856-58-4) → 2-(4-formylphenyl)pyridine (127406-56-8)

Conditions	Yield
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2h; Stage #2: 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran; toluene at 50℃; for 2.5h; Stage #3: With hydrogenchloride; ammonia; water Conversion of starting material; more than 3 stages;	100%
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h; Stage #2: 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran at 70℃; for 3.5h; Stage #3: With hydrogenchloride; ammonia; water Conversion of starting material; more than 3 stages;	99%
Stage #1: 1,1-dimethoxy-1-(4-bromophenyl)methane With iodine; magnesium In tetrahydrofuran at 30 - 35℃; for 2.5h; Stage #2: 2-bromo-pyridine; tetrakis(triphenylphosphine) palladium(0); zinc(II) chloride In tetrahydrofuran at 50℃; for 3.5h; Stage #3: With hydrogenchloride; ammonia; water Conversion of starting material; more than 3 stages;	96.4%

pyrrolidine (123-75-1) + 2-bromo-pyridine (109-04-6) → 2-pyrrolidinopyridine (54660-06-9)

Conditions	Yield
With potassium phosphate; copper(l) iodide; CVT-2537 In dimethyl sulfoxide at 90℃; for 24h; Inert atmosphere;	100%
With 1-methyl-3-(2-pyridinyl)-3,4,5,6-tetrahydropyrimidin-3-ium hexafluorophosphate; potassium tert-butylate; palladium diacetate In 1,2-dimethoxyethane at 100℃; for 0.666667h; Buchwald-Hartwig Coupling; Microwave irradiation;	97%
at 120℃; for 0.333333h; microwave irradiation;	92%

2-bromo-pyridine (109-04-6) + o-fluorophenylboronic acid (1993-03-9) → 2-(2-fluorophenyl)pyridine (89346-48-5)

Conditions	Yield
With trans-bis(triphenylphosphine)palladium dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 100℃;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Suzuki-Miyaura Coupling; Inert atmosphere; Reflux;	92%
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 12h; Suzuki-Miyaura Coupling;	90%

2-bromo-pyridine (109-04-6) + 3,5-Dimethylphenol (108-68-9) → 2-(3,5-dimethyl-phenoxy)-pyridine (28355-47-7)

Conditions	Yield
With caesium carbonate In toluene at 120℃; for 24h; Ullmann Condensation; Sealed tube;	100%
With copper(l) iodide; caesium carbonate In 4-methyl-2-pentanone at 120℃; for 24h; Ullmann type condensation; Inert atmosphere;	98%
With potassium phosphate; copper(l) iodide; (1S,2S,N1E,N2E)-N,N'-bis(pyridin-2-ylmethylene)cyclohexane-1,2-diamine In acetonitrile at 80℃; for 24h; Ullmann reaction;	97%

2-bromo-pyridine (109-04-6) + 6-ethynylquinoxaline → 6-pyridin-2-ylethynyl-quinoxaline (710946-90-0)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); N,N,N,N,-tetramethylethylenediamine In tetrahydrofuran at 55℃; for 10h;	100%

2-bromo-pyridine (109-04-6) + dimethyl(hept-1-yn-1-yl)aluminum → 2-(hept-1-yn-1-yl)pyridine (49836-16-0)

Conditions	Yield
With tris(dibenzylideneacetone)dipalladium(0) chloroform complex; 1,1'-bis-(diphenylphosphino)ferrocene In 1,2-dimethoxyethane; n-heptane at 85℃; for 0.5h;	100%

2-bromo-pyridine (109-04-6) + N-[1-(4-methoxyphenyl)prop-2-yn-1-yl]-4-methylbenzenesulfonamide (771565-23-2) → N-[1-(4-methoxyphenyl)-3-(pyridin-2-yl)-allylidene]-4-methyl-benzenesulfonamide

Conditions	Yield
With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran Heating;	100%

2-bromo-pyridine (109-04-6) + [(3-phenyl-7,8,9,10-tetrahydro-7,10-ethano[1,2,4]triazolo[3,4-a]phthalazin-6-yl)methyl]amine (848775-01-9) → C23H22N6

Conditions	Yield
at 160℃; for 6h;	100%

2-bromo-pyridine (109-04-6) + 4-acetylphenylboronic acid (149104-90-5) → 1-(4-(pyridin-2-yl)phenyl)ethanone (173681-56-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
With [(t-Bu)3PH]BF4; palladium diacetate; sodium hydroxide at 20℃; for 0.25h; Suzuki Coupling; Inert atmosphere; Glovebox;	90%
With potassium phosphate In ethanol; water at 100℃; for 8h; Suzuki-Miyaura Coupling;	82%

2-bromo-pyridine (109-04-6) + 3-acetylphenylboronic acid → 1-(3-(pyridin-2-yl)phenyl)ethan-1-one (227178-09-8)

Conditions	Yield
With palladium diacetate; potassium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 15h; Reflux; Inert atmosphere; Schlenk technique;	100%
With sodium carbonate; triphenylphosphine; palladium diacetate In propan-1-ol Suzuki-Miyaura cross-coupling; Heating;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 95℃; for 18h;
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Inert atmosphere; Schlenk technique; Reflux;

2-bromo-pyridine (109-04-6) + 2,4-difluorophenylboronic acid (144025-03-6) → 2-(2,4-difluorophenyl)pyridine (391604-55-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran at 70℃; for 24h; Suzuki coupling;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 70℃; Inert atmosphere;	98%
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 70℃; for 24h;	97%

2-bromo-pyridine (109-04-6) + 4-formylphenylboronic acid, (87199-17-5) → 2-(4-formylphenyl)pyridine (127406-56-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 8h; Suzuki coupling; Reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
Stage #1: 2-bromo-pyridine; 4-formylphenylboronic acid, With potassium carbonate In 1,4-dioxane; water for 0.5h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water Inert atmosphere; Reflux;	100%

2-bromo-pyridine (109-04-6) + (4-methoxyphenyl)manganese(II) chloride (192887-50-6) → 4-(2-pyridinyl)anisole (5957-90-4)

Conditions	Yield
Stage #1: (4-methoxyphenyl)manganese(II) chloride With 1,3-bis[2,6-bis(1-methylethyl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene monohydrochloride; bis(acetylacetonate)nickel(II) In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 2-bromo-pyridine In tetrahydrofuran at 0 - 25℃; for 1h;	100%

2-bromo-pyridine (109-04-6) + thiophene boronic acid (6165-68-0) → 2'-(2-thienyl)pyridine (3319-99-1)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; isopropyl alcohol at 80℃; for 0.666667h; Suzuki Coupling; Microwave irradiation;	91%
With bis(triphenylphosphine)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water at 80℃; for 14h;	86%

2-bromo-pyridine (109-04-6) + 4-methoxyphenylboronic acid (5720-07-0) → 4-(2-pyridinyl)anisole (5957-90-4)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 12h; Inert atmosphere; Reflux;	100%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene for 18h; Inert atmosphere; Reflux;	100%
With potassium phosphate tribasic heptahydrate; palladium diacetate In isopropyl alcohol at 80℃; for 0.2h; Suzuki coupling;	99%

2-bromo-pyridine (109-04-6) + potassium ferrocyanide → 2-Cyanopyridine (100-70-9)

Conditions	Yield
With 1-methyl-1H-imidazole; copper(l) iodide In toluene at 160℃; for 16h; Product distribution / selectivity;	100%
With 1-methyl-1H-imidazole; copper(l) iodide at 140℃; for 16h; Product distribution / selectivity;	100%
With 1,3-bis-(diphenylphosphino)propane; sodium carbonate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 130℃; for 16h; Product distribution / selectivity;	30%

Upstream product

• 110-86-1 pyridine 
• 504-29-0 2-aminopyridine 
• 14305-17-0 2-bromopyridine-N-oxide 
• 626-05-1 2,6-Dibromopyridine 
• 52200-48-3 3-bromo-2-chloropyridine 
• 109-72-8 n-butyllithium 
• 109-65-9 1-bromo-butane 
• 13534-89-9 2,3-dibromopyridine 
• 96-22-0 pentan-3-one 
• 80866-91-7 2-bromopyridine-N-oxide hydrochloride 
• 100-39-0 benzyl bromide 
• 142-08-5 2-hydroxypyridin 
• 624-28-2 2,5-dibromopyridine 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 34803-66-2 1-(2-pyridyl)piperazine 
• 64728-49-0 1,4-bis-(2-pyridyl)-1,4-diazacyclohexane 
• 145208-85-1 1-methyl-4-(pyridin-2-yl)piperazine 
• 38585-73-8 N-(2-pyridinyl)-1,3-propandiamine 
• 136575-57-0 N¹,N³-di(pyridin-2-yl)propan-1,3-diamine 
• 110-86-1 pyridine 
• 3480-65-7 [1,2']bipyridinyl-2-one 
• 10333-16-1 3-bromo-[1,2']bipyridyl-2-one 
• 1202-34-2 di(pyridin-2-yl)amine 
• 140-19-2 2-<(2-thienylmethyl)amino>pyridine 
• 122321-04-4 2-(N-methyl-N-(pyridin-2-yl)amino)ethanol 
• 1132-37-2 bis(2-pyridyl)methane 
• 77429-58-4 tris(2-pyridyl)methane 
• 53330-48-6 4-(pyridin-2-yloxy)benzoic acid ethyl ester 

Relevant articles and documents

Chlorierung und Bromierung von Pyridin-Palladium(II)-chlorid-Komplex

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Cl3CCN/PPh3 and CBr4/PPh3: Two efficient reagent systems for the preparation of N-heteroaromatic halides

Cl3CCN/PPh3 and CBr4/PPh3 are two highly reactive reagent systems for the conversion of N-heteroaromatic hydroxy compounds into N-heteroaromatic chlorides or bromides in moderate to excellent yields under mild and acid-free conditions.

TMSCH2Li and TMSCH2Li-LiDMAE: Efficient reagents for noncryogenic halogen-lithium exchange in bromopyridines

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Steric Effects on the Structures, Reactivity, and Coordination Chemistry of Tris(2-pyridyl)aluminates

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A facile bromination of hydroxyheteroarenes

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Transition-metal-free decarboxylative halogenation of 2-picolinic acids with dihalomethane under oxygen conditions

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B(C6F5)3-Catalyzed Deoxygenation of Sulfoxides and Amine N-Oxides with Hydrosilanes

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