58530-53-3

Basic information

• Product Name: 2,4-Dibromopyridine
• Synonyms: 2,4-DIBROMOPYRIDINE;2,4-DIBROMO-6-NITROPHENOL;Pyridine, 2,4-dibromo-;2,4-Dibromopyridine FP170207
• CAS NO: 58530-53-3
• Molecular Formula: C₅H₃Br₂N
• Molecular Weight: 236.89
• EINECS: -0
• Product Categories: blocks;Bromides;Pyridines;Pyridine;Heterocyclic Series;pharmacetical;Organohalides;Halides
• Mol File: 58530-53-3.mol
• Article Data: 8

Chemical Properties

• Melting Point: 38-40°C
• Boiling Point: 238°C(lit.)
• Flash Point: >110℃
• Appearance: light yellow needles
• Density: 2.059 g/cm³
• Vapor Pressure: 0.0321mmHg at 25°C
• Refractive Index: 1.607
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• Solubility: soluble in Methanol
• PKA: 0.17±0.10(Predicted)
• Sensitive: Hygroscopic
• CAS DataBase Reference: 2,4-Dibromopyridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-Dibromopyridine(58530-53-3)
• EPA Substance Registry System: 2,4-Dibromopyridine(58530-53-3)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36/37/39-36-37-22
• RIDADR: 2811
• WGK Germany: 1
• HazardClass: IRRITANT
• PackingGroup: Ⅲ
• Hazardous Substances Data: 58530-53-3(Hazardous Substances Data)

Usage

Chemical Properties

Light yellow needles

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

Synthetic route

3-deazauracil (626-03-9) → 2,4-dibromopyridine (58530-53-3) + 2,3,4-tribromopyridine (2402-91-7)

Conditions	Yield
With phosphorus(V) oxybromide at 125℃; for 4.5h;	A 90% B 9%
With phosphorus(V) oxybromide at 125℃; for 4.5h;	A 85% B 12%

2,4-dibromopyridine N-oxide (117196-08-4) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
With Acetyl bromide In acetic acid at 130℃;	80%

2-bromo-4-nitropyridine N-oxide (52092-43-0) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
With Acetyl bromide In acetic acid at 130℃; for 16h;	71%
Multi-step reaction with 2 steps 1: FeSO4; concentrated aqueous NH3 2: sodium nitrite; aqueous sulfuric acid; copper (II)-sulfate; potassium bromide / Diazotization.Reagens 4: Kupfer-Pulver; Reagens 5: Wasser View Scheme

2-bromo-4-aminopyridine (7598-35-8) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
With hydrogen bromide; bromine; sodium nitrite	60%
With sulfuric acid; copper(II) sulfate; potassium bromide; sodium nitrite Diazotization.Reagens 4: Kupfer-Pulver; Reagens 5: Wasser;

2,4-dichloropyridine (26452-80-2) → 2,4-dibromopyridine (58530-53-3)

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

4-bromo-2-picolinic acid (30766-03-1) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
With tert-butylhypochlorite; dichloromethane; oxygen; sodium hydrogencarbonate at 70℃; for 20h; Green chemistry;	45%

2,3-dibromopyridine (13534-89-9) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
Stage #1: 2,3-dibromopyridine With 2,2,6,6-tetramethyl-piperidine; n-butyllithium; ZnCl2-N,N,N’,N’-tetramethylethylenediamine In tetrahydrofuran at 20℃; for 2h; Inert atmosphere; Stage #2: With water In tetrahydrofuran Inert atmosphere; regioselective reaction;	25%
With bromine; tert.-butyl lithium; diisopropylamine 1.) THF, -60 deg C, 2.) -70 deg C, 4 h; Yield given. Multistep reaction;

3-deazauracil (626-03-9) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
With phosphorus(V) oxybromide at 130℃;

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-bromopyridine-N-oxide (14305-17-0) → 2,4-dibromopyridine (58530-53-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: concentrated sulfuric acid; nitric acid 2: FeSO4; concentrated aqueous NH3 3: sodium nitrite; aqueous sulfuric acid; copper (II)-sulfate; potassium bromide / Diazotization.Reagens 4: Kupfer-Pulver; Reagens 5: Wasser View Scheme

2-chloro-4-(trifluoromethoxy)pyridine (1206975-33-8) → 2,4-dibromopyridine (58530-53-3) + 2-bromo-4-(trifluoromethoxy)pyridine (1206977-89-0)

Conditions	Yield
With trimethylsilyl bromide In propiononitrile at 100℃; for 48h;

2,4-dibromopyridine (58530-53-3) + (2,4,6-triisopropylphenyl)magnesium bromide (108894-99-1) → 4-bromo-2-(2,4,6-triisopropylphenyl)pyridine

Conditions	Yield
With bis(tricyclohexylphosphine)nickel(II) dichloride In tetrahydrofuran at 20℃; Inert atmosphere;	100%

2,4-dibromopyridine (58530-53-3) + phenol (108-95-2) → 4-bromo-2-phenoxypyridine (1353776-73-4)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Reagent/catalyst; Solvent; Inert atmosphere; regioselective reaction;	98%

pyrrolidine (123-75-1) + 2,4-dibromopyridine (58530-53-3) → 2-bromo-4-(pyrrolidin-1-yl)-pyridine (230618-42-5)

Conditions	Yield
In ethanol at 70℃;	97%

2,4-dibromopyridine (58530-53-3) + 2-methylphenylboronic acid pinacol ester (195062-59-0) → 4-bromo-2-(2-methylphenyl)pyridine (1142194-13-5)

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 70℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	95%

2,4-dibromopyridine (58530-53-3) + 2-Methoxyphenylboronic acid (5720-06-9) → 4-bromo-2-(2-methoxyphenyl)pyridine (876601-40-0)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In tetrahydrofuran; water at 85℃; for 48h; Inert atmosphere;	94%

2,4-dibromopyridine (58530-53-3) + 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (171364-79-7) → 4-bromo-2-(4-methoxyphenyl)pyridine

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 70℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	93%

2,4-dibromopyridine (58530-53-3) + 4-methoxy-phenol (150-76-5) → C12H10BrNO2 (1415666-36-2)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; regioselective reaction;	91%

2,4-dibromopyridine (58530-53-3) + p-tolylboronic pinacol ester (195062-57-8) → 4-bromo-2-(4-methylphenyl)pyridine (916824-56-1)

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 70℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	91%

2,4-dibromopyridine (58530-53-3) + N,N-diphenyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1379789-40-8) → 2,20-(pyridine-2,4-diyl)bis(N,N-diphenylaniline)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 110℃; for 48h; Inert atmosphere; Reflux;	90%

2,4-dibromopyridine (58530-53-3) → 4-bromo-2-(4-(methylsulfonyl)phenyl)pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 16h; Inert atmosphere;	89.79%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 100℃; for 2h; Microwave irradiation; Inert atmosphere;	23%

2,4-dibromopyridine (58530-53-3) + p-cresol (106-44-5) → 4-bromo-2-p-tolyloxy-pyridine (1415666-35-1)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; regioselective reaction;	89%
Stage #1: p-cresol With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; caesium carbonate In toluene at 20℃; for 4h; Inert atmosphere; Stage #2: 2,4-dibromopyridine In toluene at 110℃; Inert atmosphere; regioselective reaction;

2,4-dibromopyridine (58530-53-3) + 2-phenyl-4,4,5,5-tetramethyl-1,3,2-dioxoborole (24388-23-6) → 2-bromo-4-phenylpyridine (54151-74-5) + 4-bromo-2-phenyl pyridine (98420-98-5)

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile for 24h; Reagent/catalyst; Temperature; Suzuki Coupling; Inert atmosphere; Reflux; regioselective reaction;	A 6% B 89%

2,4-dibromopyridine (58530-53-3) + 2-(biphenyl-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (144432-80-4) → 4-bromo-2-(4-phenylphenyl)pyridine (1514914-35-2)

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 70℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	89%

2,4-dibromopyridine (58530-53-3) + 2-([1,1’-biphenyl]-3-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (912844-88-3) → 4-bromo-2-(3-phenylphenyl)pyridine (1514914-36-3)

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 70℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	89%

2,4-dibromopyridine (58530-53-3) + 4-pyridineboronic acid pinacol ester (181219-01-2) → <4,2';4',4''>Terpyridin (116195-93-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; toluene for 120h; Inert atmosphere; Reflux;	88.7%

piperidine (110-89-4) + 2,4-dibromopyridine (58530-53-3) → 2'-bromo-3,4,5,6-tetrahydro-2H-[1,4']bipyridinyl (24255-92-3)

Conditions	Yield
In isopropyl alcohol at 75℃; for 72h;	88%

2,4-dibromopyridine (58530-53-3) + 9,9‐dimethyl‐10H‐acridine (6267-02-3) → 10,10'-(pyridine-2,4-diyl)bis(9,9-dimethyl-9,10-dihydroacridine)

Conditions	Yield
With bis(dibenzylideneacetone)-palladium(0); sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 12h; Inert atmosphere;	88%

2,4-dibromopyridine (58530-53-3) + 4-(diphenylamino)phenyl boronic acid (201802-67-7) → C41H31N3 (1352129-71-5)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; toluene at 110℃; for 48h; Suzuki coupling; Inert atmosphere;	87%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In ethanol; water; toluene at 110℃; for 48h; Suzuki coupling; Inert atmosphere;	87%

2,4-dibromopyridine (58530-53-3) + tris(3,4-dimethoxyphenyl)bismuthane (895154-77-5) → 2,4-bis(3,4-dimethoxyphenyl)pyridine

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

2,4-dibromopyridine (58530-53-3) + 4-chloro-phenol (106-48-9) → C11H7BrClNO (1415666-37-3)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; regioselective reaction;	86%

2,4-dibromopyridine (58530-53-3) + 4,4,5,5-tetramethyl-2-m-tolyl-1,3,2-dioxaborolane (253342-48-2) → 4-bromo-2-(3-methylphenyl)pyridine (1142194-16-8)

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 70℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	86%

2,4-dibromopyridine (58530-53-3) + phenylboronic acid (98-80-6) → 2-bromo-4-phenylpyridine (54151-74-5) + 2,4-diphenylpyridine (26274-35-1) + 4-bromo-2-phenyl pyridine (98420-98-5)

Conditions	Yield
With potassium phosphate; johnphos; tris(dibenzylideneacetone)dipalladium (0) In toluene at 40℃; for 24h; Suzuki cross-coupling;	A n/a B 85% C n/a
With TlOH; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water at 25℃; for 24h; Suzuki cross-coupling;	A 4% B 4% C 67%
With tetra(n-butyl)ammonium hydroxide; palladium diacetate; triphenylphosphine In tetrahydrofuran; water at 40℃; for 1h; Reagent/catalyst; Suzuki-Miyaura Coupling; Inert atmosphere;	A 61% B n/a C n/a

bromo(cyclopropyl)zinc + 2,4-dibromopyridine (58530-53-3) → 4-bromo-2-(cyclopropyl)pyridine (1086381-28-3)

Conditions	Yield
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at -20 - 20℃; for 2.16667h; Inert atmosphere;	85%
tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 20℃; for 2.16667h;	85%
With tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 0 - 20℃; for 16.1667h; Negishi Coupling;	24%

2,4-dibromopyridine (58530-53-3) + benzaldehyde (100-52-7) → (4-bromopyridin-2-yl)(phenyl)methanol

Conditions	Yield
Stage #1: 2,4-dibromopyridine With n-butyllithium In hexane; toluene at -78℃; for 2h; Stage #2: benzaldehyde In hexane; toluene at -78 - 0℃; for 5h;	85%

2,4-dibromopyridine (58530-53-3) + triethylchlorogermane (994-28-5) → C11H18BrGeN

Conditions	Yield
Stage #1: 2,4-dibromopyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 2h; Stage #2: triethylchlorogermane In diethyl ether; hexane at -78 - 20℃; for 17h;	85%

2,4-dibromopyridine (58530-53-3) + 2-(4-ethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1075719-87-7) → 4-bromo-2-(4-ethylphenyl)pyridine (1514914-34-1)

Conditions	Yield
With palladium diacetate; triphenylphosphine; potassium hydroxide In acetonitrile at 70℃; for 24h; Suzuki Coupling; Inert atmosphere; regioselective reaction;	84%

2,4-dibromopyridine (58530-53-3) + triphenylbismuthane (603-33-8) → 2,4-diphenylpyridine (26274-35-1)

Conditions	Yield
With potassium acetate; palladium diacetate; triphenylphosphine In 1-methyl-pyrrolidin-2-one at 110℃; for 2h; Schlenk technique; Inert atmosphere;	84%

2,4-dibromopyridine (58530-53-3) + phenylacetylene (536-74-3) → 4-bromo-2-(phenylethynyl)pyridine (1629220-94-5)

Conditions	Yield
With copper(l) iodide; palladium(II) trifluoroacetate; diisopropylamine; triphenylphosphine In acetonitrile for 24h; Catalytic behavior; Reagent/catalyst; Solvent; Reflux; Inert atmosphere; regioselective reaction;	84%

2,4-dibromopyridine (58530-53-3) + α-naphthol (90-15-3) → C15H10BrNO (1415666-39-5)

Conditions	Yield
With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine; caesium carbonate In dimethyl sulfoxide at 110℃; for 24h; Inert atmosphere; regioselective reaction;	83%

Upstream product

• 626-03-9 3-deazauracil 
• 7598-35-8 2-bromo-4-aminopyridine 
• 13534-89-9 2,3-dibromopyridine 
• 26452-80-2 2,4-dichloropyridine 
• 14305-17-0 2-bromopyridine-N-oxide 
• 52092-43-0 2-bromo-4-nitropyridine N-oxide 
• 117196-08-4 2,4-dibromopyridine N-oxide 
• 1206975-33-8 2-chloro-4-(trifluoromethoxy)pyridine 
• 30766-03-1 4-bromo-2-picolinic acid 

Downstream Products

• 52311-30-5 2,4-Diethoxypyridin 
• 84249-14-9 2-amino-4-bromopyridine 
• 7598-35-8 2-bromo-4-aminopyridine 
• 128071-75-0 2-bromopyridine-3-carboxaldehyde 
• 312325-74-9 (2-Bromopyridin-4-yl)acetonitrile 
• 312325-73-8 2-(4-bromopyridin-2-yl)acetonitrile 
• 458532-94-0 (2-bromopyridin-4-yl)boronic acid 
• 125311-43-5 2,4-bis[(1E)-2-phenyleth-1-enyl]pyridine 
• 916824-56-1 4-bromo-2-(p-methylphenyl)pyridine 
• 111971-30-3 2-bromo-4-(p-tolyl)pyridine 
• 134391-78-9 (2-Brom-4-pyridinyl)phenylmethanol 
• 54151-74-5 2-bromo-4-phenylpyridine 
• 26274-35-1 2,4-diphenylpyridine 
• 98420-98-5 4-bromo-2-phenyl pyridine 

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