625-92-3

Basic information

• Product Name: 3,5-Dibromopyridine
• Synonyms: 3,5-DIBROMOPYRIDINE;IFLAB-BB F1995-0190;3,5-Dibromopyridine,99%;3,5-Dibromopyridine, 98+%;3,5-dibormopyridine;3,5-DibroMopyridine, 98+% 25GR;NSC 6209;3,5-DIBROMOPYRIDINE FOR SYNTHESIS
• CAS NO: 625-92-3
• Molecular Formula: C₅H₃Br₂N
• Molecular Weight: 236.89
• EINECS: 210-916-4
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Pyridines, Pyrimidines, Purines and Pteredines;Pyridines derivates;API intermediates;Halogenated;Organohalides;Aromatics Compounds;Bromopyridines;Halopyridines;Aromatics;Bases & Related Reagents;Nucleotides;Halogenated Heterocycles;Heterocyclic Building Blocks;C5Heterocyclic Building Blocks;Brominated heterocyclic series;Boronate Ester;Boronic Acid;Potassium Trifluoroborate
• Mol File: 625-92-3.mol
• Article Data: 12

Chemical Properties

• Melting Point: 110-115 °C(lit.)
• Boiling Point: 222 °C
• Flash Point: 84.3 °C
• Appearance: White to light beige/Needle-Like Crystals
• Density: 2.0383 (rough estimate)
• Vapor Pressure: 0.155mmHg at 25°C
• Refractive Index: 1.5800 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: DMSO (Slightly, Heated), Methanol (Slightly)
• PKA: 0.52±0.20(Predicted)
• Water Solubility: Soluble in Chloroform and Methanol. Insoluble in water.
• BRN: 108477
• CAS DataBase Reference: 3,5-Dibromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 3,5-Dibromopyridine(625-92-3)
• EPA Substance Registry System: 3,5-Dibromopyridine(625-92-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-36/37/39
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 625-92-3(Hazardous Substances Data)

Usage

Chemical Properties

Light-Yellow Solid

Uses

3-Acetylamino-5-ethoxypyridine was prepared by converting 3, 5-dibromopyridine with sodium ethylate into 3-bromo-5-ethoxypyridine, allowing this substance to interact with ammonia and acetylating the aminoethoxypyridine thus formed with acetic anhydride. Lithiation of 3, 5-dibromopyridine with LDA and subsequent reaction with electrophiles provided 4-alkyl-3, 5-dibromopyridines 2 in high yield. Ligand was prepared by a Pd(0)-catalyzed cross-coupling reaction of 3,5-dibromopyridine and 5-tributylstannyl-3,3?-bipyridine. The synthesis of 3, 5-bis (2-indolyl) pyridine and 3-[(2-indolyl)-5-phenyl] pyridine derivatives as includes Stille or Suzuki type reactions, which were realized on the 3,5-dibromopyridine.

General Description

3,5-Dibromopyridine undergoes lithiation with lithium diisopropylamide and on subsequent reaction with electrophiles yields 4-alkyl-3,5-dibromopyridines.

InChI:InChI=1/C5H3Br2N/c6-4-1-5(7)3-8-2-4/h1-3H

Synthetic route

3,5-dibromopyridine-N-oxide (2402-99-5) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With titanium tetrachloride; sodium iodide In acetonitrile at 30℃; for 0.0833333h;	91%
With diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate In dichloromethane at 31℃; for 16h; Sealed tube; Irradiation;	89%
With sodium hydroxide; thiourea S,S-dioxide In ethanol at 80 - 85℃; for 2h;	81%

pyridine (110-86-1) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With thionyl chloride; sulfuric acid; bromine at 130℃; for 10h; Temperature;	82%
With tetrachloromethane; N-Bromosuccinimide; aluminium trichloride Behandeln des Reaktionsgemisches mit wss. Salzsaeure;

4-amino-3,5-dibromopyridine (84539-34-4) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With trifluoroacetic acid; isopentyl nitrite In tetrahydrofuran at 70℃; for 7h;	78%

3,5-dibromo-4-pyridinesulfonic acid (872273-27-3) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With nickel In ethanol for 4h; Reflux;	48.54%

pyridinium hydrobromide perbromide → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
Heating;	4%

pyridine (110-86-1) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine; aluminium trichloride at 100℃; for 5h; Product distribution; various ratios pyridine:bromine, various Lewis catalysts, various temperatures;
With bromine at 300℃; Leiten ueber Bimsstein oder ueber mit Kupfer(I)-bromid impraegnierten Bimsstein;
With bromine at 300℃; Leiten ueber mit Kupfer(I)-bromid oder Eisen(II)-bromid impraegnierten Bimsstein;
With bromine at 300℃; Leiten ueber Bimsstein;

Pyridine-2,3-dicarboxylic acid (89-00-9) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine at 120 - 130℃;

pyridinepentacarboxylic acid (632-49-5) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine at 170℃;

piperidine hydrochloride (6091-44-7) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine at 180℃; im Rohr;

Pyridine hydrobromide (18820-82-1) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine; acetic acid at 60 - 65℃; Abdestillieren des Eisessigs und Erhitzen des Rueckstandes auf 230-250grad;

Pyridine hydrobromide (18820-82-1) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine; acetic acid at 60 - 65℃; Abdestillieren des Eisessigs und Erhitzen des Rueckstandes auf 230-250grad;

pyridine hydrochloride (628-13-7) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine
With bromine anschliessend Erhitzen bis auf 200grad;
With bromine; mercury dichloride at 215℃;

3-bromopyridine hydrochloride (65520-08-3) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With water; bromine at 230 - 250℃; im Rohr;

N-methyl-3,5-dibromopyridinium bromide → 3,5-dibromopyridine (625-92-3) + methyl bromide (74-83-9)

Conditions	Yield
at 250℃;

3,5-dibromo-1-carboxymethyl-pyridinium; chloride + furan-2,3,5(4H)-trione pyridine (1:1) → 3,5-dibromopyridine (625-92-3)

dibromo-3,4 pyridine (13534-90-2) + pentan-3-one (96-22-0) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3) + 4-bromopyridin (1120-87-2) + bromo-3 (ethyl-1 propanol-1)-5 pyridine (107399-34-8)

Conditions	Yield
With n-butyllithium 1.) THF, hexane -60 deg C, 15 min, 2.) -60 deg C, 30 min; Yield given. Multistep reaction. Yields of byproduct given;

dibromo-3,4 pyridine (13534-90-2) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3) + 4-bromopyridin (1120-87-2)

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

piperidine (110-89-4) + hydrogenchloride (7647-01-0) + bromine (7726-95-6) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
at 180℃;

Pyridine-2,3-dicarboxylic acid (89-00-9) + bromine (7726-95-6) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
at 120 - 130℃; im Rohr;

pyridinepentacarboxylic acid (632-49-5) + bromine (7726-95-6) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
at 170℃;

acidic potassium salt of/the/ 3.5-dibromo-pyridine-tricarboxylic acid-(2.4.6) → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With methyllithium; calcium carbonate

hydrobromide of tropidine → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine at 165℃;

hydrochloride of pyridine → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With water; bromine at 200 - 210℃; im Rohr;

piperidine-N-carboxylic acid ethyl ester → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With bromine; acetic acid

x.x-dibromo-apophylline → 3,5-dibromopyridine (625-92-3)

Conditions	Yield
With hydrogenchloride at 200 - 210℃;

N-Ethoxycarbonylpiperidine (5325-94-0) + bromine (7726-95-6) → piperidine (110-89-4) + pyridine (110-86-1) + 3,5-dibromopyridine (625-92-3)

pyridine (110-86-1) + hydrogenchloride (7647-01-0) + bromine (7726-95-6) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3)

pyridine (110-86-1) + sulfuric acid (7664-93-9) + bromine (7726-95-6) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3)

pyridine (110-86-1) + hydrogenchloride (7647-01-0) + water (7732-18-5) + bromine (7726-95-6) → 3-Bromopyridine (626-55-1) + 3,5-dibromopyridine (625-92-3)

Conditions	Yield
at 200 - 210℃;

3,5-dibromopyridine (625-92-3) + ethanol (64-17-5) + carbon monoxide (201230-82-2) → diethyl 3,5-pyridinedicarboxylate (4591-56-4)

Conditions	Yield
With triethylamine; bis-triphenylphosphine-palladium(II) chloride at 100℃; under 5171.5 Torr; for 3h;	100%

3,5-dibromopyridine (625-92-3) → N-methyl-3,5-dibromopyridinium tetrafluoroborate

Conditions	Yield
With trimethoxonium tetrafluoroborate In nitromethane at 0 - 20℃; Inert atmosphere;	100%

3,5-dibromopyridine (625-92-3) + borane-THF (14044-65-6) + tris[{S}-1-{2-hydroxy-3-(1-naphthyl)naphthyl}]methane → C66H40BBr2NO3

Conditions	Yield
Stage #1: borane-THF; tris[{S}-1-{2-hydroxy-3-(1-naphthyl)naphthyl}]methane In dichloromethane at 60℃; for 8h; Glovebox; Inert atmosphere; Sealed tube; Stage #2: 3,5-dibromopyridine In dichloromethane for 0.0833333h; Glovebox; Inert atmosphere; Sealed tube;	100%

3,5-dibromopyridine (625-92-3) + 1-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)phenyl]pyrrolidin-2-one (1003309-09-8) → 1-(4-(5-bromopyridin-3-yl)phenyl)pyrrolidin-2-one

Conditions	Yield
Stage #1: 3,5-dibromopyridine; 1-[4-(4,4,5,5-tetramethyl-[1 ,3,2]dioxaborolan-2-yl)phenyl]pyrrolidin-2-one With potassium carbonate In water; butan-1-ol for 0.0833333h; Inert atmosphere; Stage #2: With bis-triphenylphosphine-palladium(II) chloride In water; butan-1-ol at 70℃; for 1h;	100%

3,5-dibromopyridine (625-92-3) → 3,5-dibromopyridine-N-oxide (2402-99-5)

Conditions	Yield
With dihydrogen peroxide; trifluoroacetic acid at 60℃; under 3750.38 Torr; Temperature;	99.7%
With phthalic anhydride; urea-hydrogen peroxide In acetonitrile for 2h; Ambient temperature;	96%
With bis-trimethylsilanyl peroxide; per-rhenic acid In dichloromethane; water at 24℃; for 24h;	88%

3,5-dibromopyridine (625-92-3) + thiophenol (108-98-5) → 3-bromo-5-phenylsulfanyl-pyridine

Conditions	Yield
Stage #1: thiophenol With sodium hydride Metallation; Stage #2: 3,5-dibromopyridine In N,N-dimethyl-formamide at 90℃; for 2h; Substitution; Further stages.;	99%
Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 3,5-dibromopyridine In N,N-dimethyl-formamide at 130℃; for 6.5h;

3,5-dibromopyridine (625-92-3) + 1-benzenesulfonyl-6-methoxy-2-tributylstannyl-1H-indole (722538-29-6) → 1-benzenesulfonyl-2-(5-bromo-pyridin-3-yl)-6-methoxy-1H-indole (1346163-28-7)

Conditions	Yield
With copper(l) iodide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 100℃; for 0.333333h; Stille cross-coupling; Inert atmosphere; Microwave irradiation;	99%

3,5-dibromopyridine (625-92-3) + 2-(5-bromopyridin-3-yl)benzo[d]oxazole (1160274-30-5) → C29H17N5O2 (1396009-36-1)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 85℃; for 16h; Inert atmosphere;	99%

3,5-dibromopyridine (625-92-3) + p-tolylboronic pinacol ester (195062-57-8) → 3,5-bis(4-methylphenyl)pyridine (26409-32-5)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; potassium hydroxide In neat (no solvent) at 110℃; for 24h; Suzuki-Miyaura Coupling; Schlenk technique; Inert atmosphere;	99%

sodium 2'‐(dicyclohexylphosphaneyl)‐2,6‐diisopropyl‐[1,1'‐biphenyl]‐3‐sulfonate + 3,5-dibromopyridine (625-92-3) + bis[(trimethylsilyl)methyl](1,5-cyclooctadiene)palladium(II) (225931-80-6) → C57H71Br2NO10P2Pd2S2(2-)*2Na(1+)

Conditions	Yield
In tetrahydrofuran at 20℃; for 1h;	99%

3,5-dibromopyridine (625-92-3) → 3-bromo-5-iodopyridine (233770-01-9)

Conditions	Yield
With iodine; isopropylmagnesium chloride In tetrahydrofuran at -10 - -5℃; for 0.0833333h;	98%
Stage #1: 3,5-dibromopyridine With nBu4ZnLi2*TMEDA In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene at 20℃; for 18h; Inert atmosphere; chemoselective reaction;	65%
Stage #1: 3,5-dibromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 25℃; for 2h; Stage #2: With iodine In tetrahydrofuran at -75 - 25℃;	61%
With iodine; isopropylmagnesium chloride In tetrahydrofuran at -78 - 20℃; for 2h;	58%
Multi-step reaction with 2 steps 1: CuSO4; methanol; NH3 / 140 °C 2: sodium nitrite; aqueous hydrochloric acid; potassium iodide / Diazotization View Scheme

3,5-dibromopyridine (625-92-3) + 4-methoxyphenylboronic acid (5720-07-0) → 3,5-bis-(4-methoxyphenyl)-pyridine (26409-33-6)

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 14h; Suzuki crosscoupling; Heating;	98%
With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; sodium carbonate In acetonitrile at 110℃; for 1h; Suzuki Coupling; Inert atmosphere;

4-Methylthiazole (693-95-8) + 3,5-dibromopyridine (625-92-3) → 3,5-bis(4-methylthiazol-5-yl)pyridine

Conditions	Yield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	98%
With C82H77Cl2N3O2Pd; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 4h;	97%

3,5-dibromopyridine (625-92-3) + pivalaldehyde (630-19-3) → C10H13Br2NO

Conditions	Yield
Stage #1: 3,5-dibromopyridine; pivalaldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With methanol; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	98%

3,5-dibromopyridine (625-92-3) + 2-methylphenyl aldehyde (529-20-4) → C13H11Br2NO

Conditions	Yield
Stage #1: 3,5-dibromopyridine; 2-methylphenyl aldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With methanol; potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h;	98%

3,5-dibromopyridine (625-92-3) + benzaldehyde (100-52-7) → (3,5-Dibromo-pyridin-4-yl)-phenyl-methanol

Conditions	Yield
Stage #1: 3,5-dibromopyridine; benzaldehyde With tris(trimethylsilyl)amine; cesium fluoride In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5h; Catalytic behavior; Reagent/catalyst; Solvent;	97%

3,5-dibromopyridine (625-92-3) + 4-methyl-2,6-dioxo-8-phenylhexahydro-[1,3,2]oxazaborolo[2,3-b][1,3,2]oxazaborol-4-ium-8-uide (109674-45-5) → 3,5-diphenylpyridine (92-07-9)

Conditions	Yield
With potassium phosphate; [Pd(η(5)-C5H5)Fe(η(5)-C5H3-C(CH3)=N-C6H4-4-CH3)Cl(P(C6H5)3)] In ethanol; water at 90℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere; Schlenk technique; Green chemistry;	96%

3,5-dibromopyridine (625-92-3) + 1-(1-methyl-piperidin-4-yl)-piperazine (23995-88-2) → 1-(5-bromopyridin-3-yl)-4-(1-methylpiperidin-4-yl)piperazine

Conditions	Yield
With 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate In toluene at 100℃; for 4h; Inert atmosphere;	96%

1-methyl-1H-imidazole (616-47-7) + 3,5-dibromopyridine (625-92-3) → 3,5-bis(1-methyl-1H-imidazol-5-yl)pyridine

Conditions	Yield
With {N,N-(1,2-diphenylethane-1,2-diylidene)bis(2-benzhydryl-4,6-dimthylaniline)}dichloropalladium; potassium carbonate; Trimethylacetic acid In N,N-dimethyl acetamide at 130℃; for 12h; Catalytic behavior;	96%

3,5-dibromopyridine (625-92-3) → 3,5-diaminopyridine (4318-78-9)

Conditions	Yield
With C24H12Cu2F9N4O7; tetrabutylammomium bromide; ammonia; caesium carbonate In water at 110 - 140℃; for 16h;	95%
With ammonium hydroxide; copper(II) sulfate at 130℃;
With ammonium hydroxide; copper; copper(II) sulfate at 130℃; for 14h; Substitution; Amination;

3,5-dibromopyridine (625-92-3) + benzaldehyde (100-52-7) → 5-bromo-α-phenyl-3-pyridinemethanol

Conditions	Yield
Stage #1: 3,5-dibromopyridine With TurboGrignard In tetrahydrofuran at -78℃; for 2h; Stage #2: benzaldehyde In tetrahydrofuran at -78 - 20℃;	95%
Stage #1: 3,5-dibromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 2h; Grignard reaction; Stage #2: benzaldehyde at 20℃; for 2h; Alkylation;	76%
Stage #1: 3,5-dibromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 1h; Substitution; Stage #2: benzaldehyde In tetrahydrofuran at 20℃; for 18h; Substitution;	76%

3,5-dibromopyridine (625-92-3) → 3,5-diiodopyridine (53710-18-2)

Conditions	Yield
With copper(l) iodide; N,N-diethylethylenediamine; sodium iodide In 1,4-dioxane at 120℃; for 18h; Schlenk technique;	95%
With copper(l) iodide; sodium iodide; N,N`-dimethylethylenediamine In 1,4-dioxane at 120℃; for 20h; Schlenk technique;	86%
Stage #1: 3,5-dibromopyridine With nBu4ZnLi2*TMEDA In toluene at 20℃; for 1h; Inert atmosphere; Stage #2: With iodine In tetrahydrofuran; toluene at 20℃; for 18h; Inert atmosphere; chemoselective reaction;	85%

3,5-dibromopyridine (625-92-3) + 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)benzo[d]oxazole → C31H19N3O2 (1396009-31-6)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 90℃; Inert atmosphere;	95%

3,5-dibromopyridine (625-92-3) + benzoimidazole (51-17-2) → 3,5-di(1H-benzimidazol-1-yl)pyridine

Conditions	Yield
With potassium carbonate; copper(II) sulfate for 24h; Reflux;	95%
With copper(l) iodide; 1,10-Phenanthroline; potassium carbonate In N,N-dimethyl-formamide at 150℃; for 72h; Inert atmosphere;	50%

3,5-dibromopyridine (625-92-3) + tri(p-tolyl)bismuth (5142-75-6) → 3,5-bis(4-methylphenyl)pyridine (26409-32-5)

Conditions	Yield
With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1.5h; Schlenk technique; Inert atmosphere;	95%

3,5-dibromopyridine (625-92-3) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → C11H16BBr2NO2

Conditions	Yield
With 1,3-di-tert-butyl-2-(neopentyloxy)-2,3-dihydro-1H-1,3,2-diazaphosphole In diethyl ether at 20℃; for 12h;	95%

3,5-dibromopyridine (625-92-3) + tris(4-methoxyphenyl)bismuth (33397-21-6) → 3,5-bis-(4-methoxyphenyl)-pyridine (26409-33-6)

Conditions	Yield
With potassium phosphate; palladium diacetate; triphenylphosphine In N,N-dimethyl-formamide at 90℃; for 1.5h; Schlenk technique; Inert atmosphere;	94%

3,5-dibromopyridine (625-92-3) + sodium methylate (124-41-4) → 3-bromo-5-methoxypyridine (50720-12-2)

Conditions	Yield
In DMF (N,N-dimethyl-formamide) at 20 - 70℃;	93%
In methanol; DMF (N,N-dimethyl-formamide) at 70℃;	93%
In methanol at 130℃; for 24h;	92%

3,5-dibromopyridine (625-92-3) + allyl bromide (106-95-6) → 3-allyl-5-bromopyridine

Conditions	Yield
Stage #1: 3,5-dibromopyridine With TurboGrignard In tetrahydrofuran at -10℃; for 0.25h; Stage #2: allyl bromide In tetrahydrofuran at 0℃; for 1h;	93%
Stage #1: 3,5-dibromopyridine With TurboGrignard In tetrahydrofuran at -15 - -10℃; for 0.25h; Stage #2: allyl bromide In tetrahydrofuran at -10℃; for 1h; Product distribution / selectivity;	93%

3,5-dibromopyridine (625-92-3) + 3-methoxyphenylboronic acid (10365-98-7) → 3,5-bis-(3-methoxyphenyl)-pyridine (15366-86-6)

Conditions	Yield
With sodium hydrogencarbonate; tetrakis(triphenylphosphine) palladium(0) In ethanol; toluene for 14h; Suzuki crosscoupling; Heating;	93%

Upstream product

• 110-86-1 pyridine 
• 65520-08-3 3-bromopyridine hydrochloride 
• 110-89-4 piperidine 
• 7647-01-0 hydrogenchloride 
• 7726-95-6 bromine 
• 89-00-9 Pyridine-2,3-dicarboxylic acid 
• 632-49-5 pyridinepentacarboxylic acid 
• 5325-94-0 N-Ethoxycarbonylpiperidine 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 529-18-0 tropidine 
• 10035-10-6 hydrogen bromide 
• 618-42-8 1-piperidin-1-yl-ethanone 
• 872273-27-3 3,5-dibromopyridine-4-sulfonic acid 

Downstream Products

• 200064-13-7 4-(5-bromopyridin-3-yl) morpholine 
• 200064-39-7 4-(3-Bromo-pyridin-4-yl)-morpholine 
• 130722-95-1 3-(benzyloxy)-5-bromopyridine 
• 4318-78-9 3,5-diaminopyridine 
• 13535-01-8 3-amino-5-bromopyridine 
• 75806-85-8 2,3,5-tribromopyridine 
• 2766-64-5 2,3,5,6-tetrabromopyridine 
• 477723-55-0 3,5-bis[(E)-2-phenylethenyl]pyridine 
• 639011-64-6 3-bromo-5-trimethylsilylethynylpyridine 
• 753483-57-7 (5-Bromo-pyridin-3-yl)-((S)-1-phenyl-ethyl)-amine 
• 742108-76-5 C₂₃H₁₇NO₄ 
• 92-07-9 3,5-diphenylpyridine 
• 675590-28-0 3-bromo-5-(4-methylphenyl)pyridine 
• 171820-00-1 4,4'-pyridine-3,5-diyldibenzaldehyde 

Relevant articles and documents

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Synthesis, catalytic activity and medium fluorous recycle of fluorous analogues of PEPPSI catalysts

PEPPSI complexes are air and moisture stable Pd catalysts, which can be used conveniently in many coupling reactions. With the aim to obtain Pd catalysts recyclable by fluorous separation methods, we modified the structure of commercial PEPPSI complexes by per- or polyfluoroalkylation in various positions. The modifications included the use of a linear polyfluoroalkyl group instead of one aryl group on the NHC ligand, perfluoroalkylation of pyridine ligand, and substitution of chloride ligands on Pd for perfluoroalkanoates or perfluoropolyoxaalkanoates. Comparison of catalytic activity of commercial catalysts with the modified ones in Suzuki-Miyaura cross-coupling reactions showed that the fluorous modifications mostly resulted in the increase of catalytic activity. Moreover, polyfluoroalkylation enabled efficient medium fluorous recycle of the modified catalysts using a two phase aqueous DMF/HFE 7500 ether system.

Catalytic Deoxygenation of Amine and Pyridine N-Oxides Using Rhodium PCcarbeneP Pincer Complexes

Rhodium PCcarbeneP pincer complexes 1-L (L = PPh3, PPh2(C6F5), PCy3) readily facilitate deoxygenation of amine and pyridine N-oxides. The resulting complexes exhibit δ2-C= O coordination of the resulting keto POP pincer ligand. These δ2-Ca? O linkages in the metalloepoxide complexes are readily reduced by isopropyl alcohol and various benzylic alcohols. Thus, efficient catalytic deoxygenation of amine and pyridine N-oxides is possible using complexes 1-L and isopropyl alcohol. This represents a pioneering example of PCcarbeneP pincer complexes being used as catalysts for catalytic deoxygenation.