2587-00-0

Basic information

• Product Name: 2,6-DICHLOROPYRIDINE N-OXIDE
• Synonyms: 2,6-DICHLOROPYRIDINE N-OXIDE;AURORA KA-6496;AURORA KA-3003;2,6-Dichloropyridine-N-oxide,98%;2,6-dichloro-2,3-dihydropyridin-3-one;NSC 136569;2,6-Dichloropyridine N-oxide 98%;2,6-dichloro-1-oxidopyridin-1-ium
• CAS NO: 2587-00-0
• Molecular Formula: C₅H₃Cl₂NO
• Molecular Weight: 163.99
• Product Categories: Heterocyclic Compounds;Nucleotides and Nucleosides;Bases & Related Reagents;Nucleotides;C5Heterocyclic Building Blocks;Halogenated Heterocycles;Heterocyclic Building Blocks;Pyridines;Building Blocks;C5;C5 to C6;Chemical Synthesis;Halogenated Heterocycles;Heterocyclic Building Blocks;Heterocycle-Pyridine series
• Mol File: 2587-00-0.mol
• Article Data: 26

Chemical Properties

• Melting Point: 138-142 °C(lit.)
• Boiling Point: 344.2 °C at 760 mmHg
• Flash Point: 162 °C
• Appearance: White to creamish or light yellow/Powder or Crystals
• Density: 1.47 g/cm³
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Chloroform
• PKA: -2.26±0.10(Predicted)
• CAS DataBase Reference: 2,6-DICHLOROPYRIDINE N-OXIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-DICHLOROPYRIDINE N-OXIDE(2587-00-0)
• EPA Substance Registry System: 2,6-DICHLOROPYRIDINE N-OXIDE(2587-00-0)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 36/37/39-26-22
• RIDADR: UN2811
• WGK Germany: 3
• HazardClass: 6.1
• Hazardous Substances Data: 2587-00-0(Hazardous Substances Data)

Usage

Chemical Properties

Orange-Yellow Crystals

Uses

2,6-Dichloropyridine-1-oxide (cas# 2587-00-0) is a compound useful in organic synthesis.

InChI:InChI=1/C5H4Cl2NO/c6-4-2-1-3-5(7)8(4)9/h1-4H/q+1

Synthetic route

2,6-dichloropyridine (2402-78-0) → 2,6-dichloropyridine N-oxide (2587-00-0)

Conditions	Yield
With dihydrogen peroxide; trifluoroacetic acid at 80℃; for 2h; Reagent/catalyst; Temperature;	90.15%
With dihydrogen peroxide; trifluoroacetic acid In water at 0℃; for 6.5h; Reflux;	87.6%
With dihydrogen peroxide; trifluoroacetic acid In water for 6.5h; Reflux;	87.6%

2,6-dichloropyridine (2402-78-0) + dihydrogen peroxide (7722-84-1) → 2,6-dichloropyridine N-oxide (2587-00-0)

Conditions	Yield
With trifluoroacetic acid

2,6-dichloropyridine N-oxide (2587-00-0) → 2,6-dichloropyridine (2402-78-0)

Conditions	Yield
With 2-methyl-but-2-ene; trans-dioxo(5,10,15,20-tetramesitylporphirinato)ruthenium(VI) In benzene at 30℃; for 15h;	94%
With (4,4′-di-tert-butyl-2,2′-bipyridine)bis[(2-pyridinyl)phenyl]iridium(III) hexafluorophosphate; di-tert-butyl 1,4-dihydro-2,6-dimethyl-3,5-pyridine-dicarboxylate In acetonitrile at 20℃; for 0.75h; Inert atmosphere; Irradiation; chemoselective reaction;	92%
With ammonium formate; silica gel; zinc In methanol at 20℃; for 0.166667h; chemoselective reaction;	88%

2,6-dichloropyridine N-oxide (2587-00-0) + octanol (111-87-5) → 1-hydroxy-6-(octyloxy)pyridine-2(1H)-one (162912-64-3)

Conditions	Yield
With sodium hydroxide In water at 20 - 120℃; pH=3.5 - 4.0; Reflux;	90.6%

2,6-dichloropyridine N-oxide (2587-00-0) → 2,4,6-trichloropyridine (16063-69-7)

Conditions	Yield
With trichlorophosphate for 4h; Reflux;	85%
With trichlorophosphate for 4h; Reflux;	85%
With trichlorophosphate for 4h; Reflux;	85%

2,6-dichloropyridine N-oxide (2587-00-0) → C5H4BCl2NO3 (1415388-29-2)

Conditions	Yield
With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; bis(pinacol)diborane; 4,4'-di-tert-butyl-2,2'-bipyridine	85%

2,6-dichloropyridine N-oxide (2587-00-0) + allyl (4-bromophenyl)sulfide (6334-55-0) + phenylacetylene (536-74-3) → 2-(4-bromophenylthio)-1-phenylpent-4-en-1-one

Conditions	Yield
With Mor-DaIPhos-AuCl; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 60℃; for 20h;	77%

2,6-dichloropyridine N-oxide (2587-00-0) → 2-chloropyridine (109-09-1) + 2,6-dichloropyridine (2402-78-0)

Conditions	Yield
With copper(l) iodide; zinc In ethanol at 55 - 60℃; for 3h;	A n/a B 75%

2,6-dichloropyridine N-oxide (2587-00-0) + [(N,N’-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)Ge{CH(SiMe3)2}][(3,5-(CF3)2C6H3)4] → C32H12BF24(1-)*C39H58Cl2GeN3O2Si2(1+)

Conditions	Yield
In fluorobenzene at 20℃; for 0.0833333h; Inert atmosphere;	73%

1-allylsulfanyl-4-chloro-benzene (15446-14-7) + 2,6-dichloropyridine N-oxide (2587-00-0) + phenylacetylene (536-74-3) → 2-(4-chlorophenylthio)-1-phenylpent-4-en-1-one

Conditions	Yield
With Mor-DaIPhos-AuCl; sodium tetrakis[(3,5-di-trifluoromethyl)phenyl]borate In 1,2-dichloro-ethane at 60℃; for 8h;	70%

2,6-dichloropyridine N-oxide (2587-00-0) → 2,6-dichloro-4-nitro-pyridine (25194-01-8)

Conditions	Yield
Stage #1: 2,6-dichloropyridine N-oxide With sulfuric acid; nitric acid In water at 148 - 156℃; for 1h; Stage #2: With ammonia In water pH=6;	66.4%
Stage #1: 2,6-dichloropyridine N-oxide With sulfuric acid; nitric acid at 148 - 156℃; for 1h; Stage #2: With ammonia In water at 20℃; pH=6;	66.4%
With sulfuric acid; nitric acid for 15h; Heating;	25%
With sulfuric acid; nitric acid at 160℃;

2,6-dichloropyridine N-oxide (2587-00-0) → 2-amino-6-chloropyridine N-oxide

Conditions	Yield
With ammonia In methanol at 105℃; for 26h;	55%

2,6-dichloropyridine N-oxide (2587-00-0) + 2-ethyl-7-mercapto-8-methyl-4H-chromen-4-one (1362586-97-7) → 7-(6-chloropyridin-2-ylthio)-2-ethyl-8-methyl-4H-chromen-4-one N-oxide (1362586-28-4)

Conditions	Yield
With pyridine at 20℃; for 2h;	53%
With pyridine for 2h; Reflux;	53%

2,6-dichloropyridine N-oxide (2587-00-0) + 2-ethyl-7-mercapto-4H-chromen-4-one (1337971-33-1) → 7-(6-chloropyridin-2-ylthio)-2-ethyl-4H-chromen-4-one N-oxide (1362586-25-1)

Conditions	Yield
With pyridine at 20℃; for 2h;	51%

2-(trifluoromethoxy)biphenylyl-2'-diazonium hexafluoroantimonate + 2,6-dichloropyridine N-oxide (2587-00-0) → N-trifluoromethoxy-2,6-dichloropyridinium hexafluoroantimonate

Conditions	Yield
In dichloromethane at 42℃; for 3.5h; Sealed tube; Inert atmosphere;	51%

2,6-dichloropyridine N-oxide (2587-00-0) + 7-mercapto-4-methyl-2H-chromen-2-one (137215-27-1) → 7-(6-chloropyridin-2-ylthio)-4-methyl-2H-chromen-2-one N-oxide (1141172-55-5)

Conditions	Yield
With pyridine at 20℃; for 2h;	48%
With pyridine for 2h; Reflux;	48%

2,6-dichloropyridine N-oxide (2587-00-0) + tert-butylmagnesium chloride (677-22-5) → 2-(tert-butyl)-6-chloropyridine 1-oxide

Conditions	Yield
With copper(l) iodide In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	45%

2,6-dichloropyridine N-oxide (2587-00-0) → 2-Chloropyridinyl 6-disulfide (72917-33-0)

Conditions	Yield
With thiourea In ethanol for 2h; Heating;	40%

Togni's reagent (887144-97-0) + 2,6-dichloropyridine N-oxide (2587-00-0) + trimethylsilyl bis(trifluoromethanesulfonyl)imide (82113-66-4) → 2,6-dichloro-N-(trifluoromethoxy)pyridinium triflimide

Conditions	Yield
Stage #1: 2,6-dichloropyridine N-oxide; trimethylsilyl bis(trifluoromethanesulfonyl)imide In dichloromethane at 20℃; Schlenk technique; Inert atmosphere; Glovebox; Stage #2: Togni's reagent In dichloromethane at 20℃; for 12h; Schlenk technique; Inert atmosphere; Glovebox;	39%

2,6-dichloropyridine N-oxide (2587-00-0) → 2-hydroxylamino-6-chloropyridine 1-oxide (72647-13-3)

Conditions	Yield
With hydroxylamine In ethanol for 144h; Ambient temperature;	24%

2,6-dichloropyridine N-oxide (2587-00-0) + C32H50FeN4 (1433221-40-9) → C64H100Fe2N8O (1433221-44-3)

Conditions	Yield
In benzene at -78 - 20℃; for 8h; Inert atmosphere;	18%

2,6-dichloropyridine N-oxide (2587-00-0) + isopropylamine (75-31-0) → (6-chloro-1-oxy-pyridin-2-yl)-isopropyl-amine (59618-29-0)

Conditions	Yield
In hexane; dimethyl sulfoxide	15.01%

piperidine (110-89-4) + 2,6-dichloropyridine N-oxide (2587-00-0) → 6'-chloro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl 1'-oxide (59618-35-8)

Conditions	Yield
In hexane; benzene	12.9%

2,6-dichloropyridine N-oxide (2587-00-0) + 3-Chlorostyrene (2039-85-2) → 2,6-dichloropyridine (2402-78-0) + (R)-meta-chlorostyrene oxide (20697-04-5, 53631-04-2, 115648-90-3, 62600-71-9) + (S)-3-chlorostyrene oxide (115648-90-3)

Conditions	Yield
chiral ruthenium porphyrin complex catalyst In toluene at -10℃; for 48h; Title compound not separated from byproducts.;

4-vinylbenzyl chloride (1073-67-2) + 2,6-dichloropyridine N-oxide (2587-00-0) → 2,6-dichloropyridine (2402-78-0) + (R)-2-(4-chlorophenyl)oxirane (2788-86-5, 53649-47-1, 97466-49-4, 21019-51-2) + (2S)-2-(4-chlorophenyl)oxirane (2788-86-5, 21019-51-2, 53649-47-1, 97466-49-4)

Conditions	Yield
chiral ruthenium porphyrin complex catalyst In toluene at -10℃; for 48h; Title compound not separated from byproducts.;

1-propenylbenzene (873-66-5) + 2,6-dichloropyridine N-oxide (2587-00-0) → 2,6-dichloropyridine (2402-78-0) + (1S,2S)-(-)-1-phenyl-1-propene oxide (4518-66-5) + (+)-(R,R)-β-methylstyrene oxide (14212-54-5)

Conditions	Yield
chiral ruthenium porphyrin complex catalyst In toluene at -10℃; for 48h; Title compound not separated from byproducts.;

styrene (292638-84-7) + 2,6-dichloropyridine N-oxide (2587-00-0) → 2,6-dichloropyridine (2402-78-0) + (R)-Styrene oxide (20780-53-4) + (S)-styrene oxide (20780-54-5)

Conditions	Yield
chiral ruthenium porphyrin complex catalyst In toluene at -10℃; for 48h; Title compound not separated from byproducts.;

2,6-dichloropyridine N-oxide (2587-00-0) → 8-chloro-3-deazaadenine

Conditions	Yield
Multi-step reaction with 10 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 51 percent / Fe / 2 h / Heating 6: aq. NaOH / Heating 7: 96 percent / Ac2O / 4.5 h / Heating 8: 49 percent / ammonia / methanol / 90 h / 160 °C 9: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 10: 31 percent / t-butyl hypochlorite / dimethylsulfoxide / 144 h / 20 °C View Scheme
Multi-step reaction with 10 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 51 percent / Fe / 2 h / Heating 6: aq. NaOH / Heating 7: 96 percent / Ac2O / 4.5 h / Heating 8: 49 percent / ammonia / methanol / 90 h / 160 °C 9: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 10: HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 6: 96 percent / Ac2O / 4.5 h / Heating 7: 49 percent / ammonia / methanol / 90 h / 160 °C 8: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 9: 31 percent / t-butyl hypochlorite / dimethylsulfoxide / 144 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 6: 96 percent / Ac2O / 4.5 h / Heating 7: 49 percent / ammonia / methanol / 90 h / 160 °C 8: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 9: HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme

2,6-dichloropyridine N-oxide (2587-00-0) → 3-chloro-3-deazaadenine

Conditions	Yield
Multi-step reaction with 10 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 51 percent / Fe / 2 h / Heating 6: aq. NaOH / Heating 7: 96 percent / Ac2O / 4.5 h / Heating 8: 49 percent / ammonia / methanol / 90 h / 160 °C 9: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 10: 6.2 percent / HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme
Multi-step reaction with 9 steps 1: HNO3; H2SO4 / 160 °C 2: AcOH; Fe / Heating 3: HNO3; H2SO4 / 20 °C 4: H2SO4 / 100 °C 5: 94 percent / Fe; H2O; HCl / ethanol / 16 h / 95 °C 6: 96 percent / Ac2O / 4.5 h / Heating 7: 49 percent / ammonia / methanol / 90 h / 160 °C 8: 72 percent / NaOH; H2 / Pd/C / H2O / 20 h / 1758.3 Torr 9: 6.2 percent / HCl; mCPBA / N,N-dimethyl-acetamide / 0.42 h / 20 °C View Scheme

Upstream product

• 2402-78-0 2,6-dichloropyridine 
• 7722-84-1 dihydrogen peroxide 

Downstream Products

• 2402-78-0 2,6-dichloropyridine 
• 16063-69-7 2,4,6-trichloropyridine 
• 25194-01-8 4-nitro-2,6-dichloro-pyridine 
• 109-09-1 2-chloropyridine 
• 1415388-25-8 C₂₂H₂₁N₃O₃ 
• 1415388-30-5 C₁₁H₇Cl₂NO 
• 1415388-31-6 C₁₃H₁₂ClNO₃ 
• 1415388-32-7 C₂₀H₁₇N₃O₃ 
• 1415388-33-8 C₂₄H₂₅N₃O₄ 

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