22710-07-2

Basic information

• Product Name: 2,3-Dimethylpyridine-N-oxide
• Synonyms: 2,3-DIMETHYLPYRIDINE N-OXIDE;2,3-DIMETHYL-4-PYRIDINE-N-OXIDE;2,3-LUTIDINE-N-OXIDE;2,3-Dimethylpyridine N-oxide ,98%;2,3-Lutidine 1-oxide
• CAS NO: 22710-07-2
• Molecular Formula: C₇H₉NO
• Molecular Weight: 123.15
• Mol File: 22710-07-2.mol
• Article Data: 43

Chemical Properties

• Melting Point: 85-93 °C
• Boiling Point: 298.1 °C at 760 mmHg
• Flash Point: 134.1 °C
• Appearance: /
• Density: 1 g/cm³
• Vapor Pressure: 0.00229mmHg at 25°C
• Refractive Index: 1.509
• PKA: 1.38±0.10(Predicted)
• CAS DataBase Reference: 2,3-Dimethylpyridine-N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-Dimethylpyridine-N-oxide(22710-07-2)
• EPA Substance Registry System: 2,3-Dimethylpyridine-N-oxide(22710-07-2)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39
• Hazardous Substances Data: 22710-07-2(Hazardous Substances Data)

Usage

Chemical Properties

White solid

Uses

2,3-Lutidine-N-oxide can be used in biological study of enzymic reduction of pyridine- and nitropyridine-N-oxide derivs. by ferredoxin-NADP+ oxidoreductase and the role of their electron accepting potency.

InChI:InChI=1/C7H9NO/c1-6-4-3-5-8(9)7(6)2/h3-5H,1-2H3

Synthetic route

2,3-Lutidine (583-61-9) → 2,3-dimethylpyridine 1-oxide (22710-07-2)

Conditions	Yield
With sodium tungstate; dihydrogen peroxide In water at 55℃; for 3h; Temperature;	99%
With 3-chloro-benzenecarboperoxoic acid In Isopropyl acetate at 10 - 35℃; for 5.83333h; Green chemistry;	98.9%
With △-Na8H[PW9O34]·19H2O; dihydrogen peroxide In water at 20℃; for 24h; Green chemistry;	94%

2,3-Lutidine (583-61-9) + formaldehyd (50-00-0) → 2,3-dimethylpyridine 1-oxide (22710-07-2)

Conditions	Yield
With sulfuric acid; dihydrogen peroxide In acetic acid

2,3-Lutidine (583-61-9) + 3-chloro-benzenecarboperoxoic acid (937-14-4) → 2,3-dimethylpyridine 1-oxide (22710-07-2)

Conditions	Yield
With sodium sulfite In dichloromethane; Petroleum ether

2,3-dimethylpyridine 1-oxide (22710-07-2) → 2-hydroxymethyl-3-methyl pyridine (63071-09-0)

Conditions	Yield
With trifluoroacetic anhydride In dichloromethane at 23℃; for 40h; Inert atmosphere; Schlenk technique;	96%
Multi-step reaction with 2 steps 1: 81 percent / 1 h / Heating 2: 81 percent / 1 N NaOH / methanol / 1.5 h / 25 °C View Scheme
Multi-step reaction with 2 steps 1: AcOH / 120 °C 2: 2N aq. NaOH / methanol / 2 h / 25 °C View Scheme
Stage #1: 2,3-dimethylpyridine 1-oxide In dichloromethane at 0℃; Stage #2: With trifluoroacetic anhydride at 20 - 45℃; for 7h;

2,3-dimethylpyridine 1-oxide (22710-07-2) → 2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7)

Conditions	Yield
With potassium nitrite; sulfuric acid at -10 - 85℃; for 2h; Temperature; Green chemistry;	92.9%
With sulfuric acid; nitric acid at 100℃; for 5h;	78%
With sulfuric acid; nitric acid at 95℃; for 20h;	53%

2,3-dimethylpyridine 1-oxide (22710-07-2) → 2,3-dimethyl-4-bromopyridine N-oxide (259807-92-6)

Conditions	Yield
With bromine In water at 0 - 35℃; for 6h; Temperature;	92%

2,3-dimethylpyridine 1-oxide (22710-07-2) + 5-bromo-1,3-xylene (556-96-7) → 2-(3,5-dimethylbenzyl)-3-methylpyridine 1-oxide (1151985-86-2)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; XPhos In toluene at 110℃; for 0.75h; Inert atmosphere; Microwave irradiation;	90%

2,3-dimethylpyridine 1-oxide (22710-07-2) + acetic anhydride (108-24-7) → 2-(acetoxymethyl)-3-methylpyridine (52814-41-2)

Conditions	Yield
for 1h; Heating;	81%

2,3-dimethylpyridine 1-oxide (22710-07-2) + 1-Heptyne (628-71-7) + bis(trifluoromethanesulfonyl)amide (82113-65-3) → 1-(hept-1-en-2-yloxy)-2,3-dimethylpyridin-1-ium bis((trifluoromethyl)sulfonyl)amide

Conditions	Yield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) at 20℃; for 5h;	81%

2,3-dimethylpyridine 1-oxide (22710-07-2) + para-bromotoluene (106-38-7) → 3-methyl-2-(4-methylbenzyl)pyridine 1-oxide (1151985-88-4)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In toluene at 70℃; Inert atmosphere;	76%

2,3-dimethylpyridine 1-oxide (22710-07-2) + trimethylsilyl cyanide (7677-24-9) → 5,6-dimethylpyridine-2-carbonitrile (59146-67-7)

Conditions	Yield
With N,N-Dimethylcarbamoyl chloride In dichloromethane at 20℃; for 72h;	75%
With N,N-diethylcarbamyl chloride In dichloromethane at 20℃; for 60h; Inert atmosphere;	53%
With N,N-diethylcarbamyl chloride In 1,2-dichloro-ethane Ambient temperature;

2,3-dimethylpyridine 1-oxide (22710-07-2) + cinnamyl acetate (103-54-8) → C14H15N

Conditions	Yield
With tetrafluoroboric acid; 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate In dichloromethane; water at 20℃; for 48h; Inert atmosphere; Sealed tube; Irradiation;	64%

2,3-dimethylpyridine 1-oxide (22710-07-2) + cyclohexyltrifluoro-λ4-borane potassium salt (446065-11-8) → 6-cyclohexyl-2,3-dimethylpyridine N-oxide

Conditions	Yield
With tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; 1-acetoxy-1,2-benziodoxol-3-one; trifluoroacetic acid In dichloromethane; water at 20℃; for 24h; Schlenk technique; Inert atmosphere; Irradiation;	55%

2,3-dimethylpyridine 1-oxide (22710-07-2) + cinnamyl propionate (78761-38-3, 103-56-0) → C14H15N

Conditions	Yield
With tetrafluoroboric acid; 10-phenyl-9-(2,4,6-trimethylphenyl)acridinium tetrafluoroborate In dichloromethane; water at 20℃; for 144h; Inert atmosphere; Sealed tube; Irradiation;	54%

2,3-dimethylpyridine 1-oxide (22710-07-2) → 4-chloro-2,3-dimethylpyridine-N-oxide (59886-90-7)

Conditions	Yield
Stage #1: 2,3-dimethylpyridine 1-oxide With chlorine In dichloromethane at 25℃; for 1.5h; Green chemistry; Stage #2: With sodium hydroxide In dichloromethane at 25℃; Green chemistry;	49%
Multi-step reaction with 2 steps 1: 53 percent / conc. H2SO4, 65percent HNO3 / 20 h / 95 °C 2: 53 percent / conc. HCl / 12 h / 170 °C View Scheme
Multi-step reaction with 2 steps 1: sulfuric acid; nitric acid / water / 5 h / 95 °C 2: acetyl chloride / ethanol / 5 h / 65 °C View Scheme

2,3-dimethylpyridine 1-oxide (22710-07-2) + phenyl isocyanate (103-71-9) → 2-[(3aS,7aS)-6-Methyl-2-oxo-3-phenyl-2,3,3a,7a-tetrahydro-4H-oxazolo[4,5-b]pyridin-(5Z)-ylidene]-N-phenyl-acetamide (80025-35-0)

Conditions	Yield
In xylene at 140℃; for 3.5h;	40%

2,3-dimethylpyridine 1-oxide (22710-07-2) + p-chlorphenylisocyanate (104-12-1) → N-(4-Chloro-phenyl)-2-[(3aS,7aS)-3-(4-chloro-phenyl)-6-methyl-2-oxo-2,3,3a,7a-tetrahydro-4H-oxazolo[4,5-b]pyridin-(5Z)-ylidene]-acetamide (106411-66-9)

Conditions	Yield
In xylene at 140℃; for 3.5h;	38%

2,3-dimethylpyridine 1-oxide (22710-07-2) + p-Tolylisocyanate (622-58-2) → 2-[(3aS,7aS)-6-Methyl-2-oxo-3-p-tolyl-2,3,3a,7a-tetrahydro-4H-oxazolo[4,5-b]pyridin-(5Z)-ylidene]-N-p-tolyl-acetamide (106411-65-8)

Conditions	Yield
In xylene at 140℃; for 3.5h;	36%

2,3-dimethylpyridine 1-oxide (22710-07-2) + para-bromotoluene (106-38-7) → 2,3-dimethyl-6-(4-methylphenyl)pyridine-N-oxide (1127561-91-4)

Conditions	Yield
With palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; Inert atmosphere;	34%

N-methylmaleimide (930-88-1) + 2,3-dimethylpyridine 1-oxide (22710-07-2) → (4aS,5aS,8aR,8bS)-2-[Bis-(1-methyl-2,5-dioxo-pyrrolidin-3-yl)-methyl]-3,7-dimethyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione (134220-49-8)

Conditions	Yield
In toluene for 10h; Heating;	25.7%

2,3-dimethylpyridine 1-oxide (22710-07-2) + N-(4-chlorophenyl)maleimide (1631-29-4) → (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-chloro-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-chloro-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione (134220-45-4)

Conditions	Yield
In toluene for 10h; Heating;	24.1%

2,3-dimethylpyridine 1-oxide (22710-07-2) + N-(4-bromophenyl)maleimide (13380-67-1) → (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-bromo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-bromo-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione (134220-47-6)

Conditions	Yield
In toluene for 10h; Heating;	22.2%

2,3-dimethylpyridine 1-oxide (22710-07-2) + phenyl isocyanate (103-71-9) → 2,3,3a,4,5,7a-hexahydro-6-methyl-2-oxo-3-phenyl-5-(N-phenylcarbamoyl)methylene-oxazolo<4,5-b>pyridine (80025-35-0)

Conditions	Yield
In N,N-dimethyl-formamide at 110℃; for 7h;	21%

2,3-dimethylpyridine 1-oxide (22710-07-2) + N-cyclohexylmaleimide (1631-25-0) → (4aS,5aS,8aR,8bS)-2-[Bis-(1-cyclohexyl-2,5-dioxo-pyrrolidin-3-yl)-methyl]-7-cyclohexyl-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione (134220-50-1)

Conditions	Yield
In toluene for 10h; Heating;	20.5%

2,3-dimethylpyridine 1-oxide (22710-07-2) + n-butylmaleimide (2973-09-3) → (4aS,5aS,8aR,8bS)-2-[Bis-(1-butyl-2,5-dioxo-pyrrolidin-3-yl)-methyl]-7-butyl-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione (134220-46-5)

Conditions	Yield
In toluene for 10h; Heating;	20%

2,3-dimethylpyridine 1-oxide (22710-07-2) → 2-[(3aS,7aS)-6-Methyl-2-oxo-3-phenyl-2,3,3a,7a-tetrahydro-4H-oxazolo[4,5-b]pyridin-(5Z)-ylidene]-N-phenyl-acetamide (80025-35-0)

Conditions	Yield
With benzophenone In N,N-dimethyl-formamide at 110℃; for 7h; Product distribution; Kinetics; Thermodynamic data; mechanism; Ea; ΔS(excit.); different disubstituted pyridine N-oxides, phenyl isocyanates, molar ratios, solvent, reaction times and temperatures; without benzophenone;	20%

2,3-dimethylpyridine 1-oxide (22710-07-2) + N-phenyl-maleimide (941-69-5) → (4aS,5aS,8aR,8bS)-2-[Bis-(2,5-dioxo-1-phenyl-pyrrolidin-3-yl)-methyl]-3-methyl-7-phenyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione (134220-44-3)

Conditions	Yield
In toluene for 10h; Mechanism; Heating; other N-substituted maleimides;	18.3%
In toluene for 10h; Heating;	18.3%

2,3-dimethylpyridine 1-oxide (22710-07-2) + 1-(4-iodophenyl)-1H-pyrrole-2,5-dione (65833-01-4) → (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-iodo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-iodo-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione (134220-48-7)

Conditions	Yield
In toluene for 10h; Heating;	17.1%

phosgene (75-44-5) + 2,3-dimethylpyridine 1-oxide (22710-07-2) → C8H9ClNO2(1+)*Cl(1-)

Conditions	Yield
In dichloromethane at 25℃; Rate constant;

2,3-dimethylpyridine 1-oxide (22710-07-2) + potassium cyanide (151-50-8) → 4-cyano-2,3-dimethylpyridine (131895-50-6)

Conditions	Yield
With dimethyl sulfate 1.) 14 h, r.t., 2.) 50percent aq. EtOH, 14 h, r.t.; Yield given. Multistep reaction;

2,3-dimethylpyridine 1-oxide (22710-07-2) → 3-methoxy-2-methyl-6-nitropyridine 1-oxide (35392-67-7) + 2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7)

Conditions	Yield
With nitric acid In acetic acid at 80℃; for 33h;

2,3-dimethylpyridine 1-oxide (22710-07-2) → (2E,4Z)-5-Cyano-3-methyl-penta-2,4-dien-2-ol anion

Conditions	Yield
With sodium hydroxide In water at 17℃; Rate constant; Irradiation;

Upstream product

• 583-61-9 2,3-Lutidine 
• 937-14-4 3-chloro-benzenecarboperoxoic acid 
• 50-00-0 formaldehyd 

Downstream Products

• 52814-41-2 2-(acetoxymethyl)-3-methylpyridine 
• 37699-43-7 2,3-dimethyl-4-nitropyridine N-oxide 
• 4377-43-9 2-chloromethyl-3-methyl-pyridine 
• 59146-67-7 5,6-dimethylpyridine-2-carbonitrile 
• 80025-35-0 2-[(3aS,7aS)-6-Methyl-2-oxo-3-phenyl-2,3,3a,7a-tetrahydro-4H-oxazolo[4,5-b]pyridin-(5Z)-ylidene]-N-phenyl-acetamide 
• 35392-67-7 3-methoxy-2-methyl-6-nitropyridine 1-oxide 
• 134220-47-6 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-bromo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-bromo-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 106411-65-8 2-[(3aS,7aS)-6-Methyl-2-oxo-3-p-tolyl-2,3,3a,7a-tetrahydro-4H-oxazolo[4,5-b]pyridin-(5Z)-ylidene]-N-p-tolyl-acetamide 
• 131895-50-6 4-cyano-2,3-dimethylpyridine 
• 106411-66-9 N-(4-Chloro-phenyl)-2-[(3aS,7aS)-3-(4-chloro-phenyl)-6-methyl-2-oxo-2,3,3a,7a-tetrahydro-4H-oxazolo[4,5-b]pyridin-(5Z)-ylidene]-acetamide 
• 134220-48-7 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-iodo-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-iodo-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 134220-45-4 (4aR,5aR,8aS,8bR)-2-{Bis-[1-(4-chloro-phenyl)-2,5-dioxo-pyrrolidin-3-yl]-methyl}-7-(4-chloro-phenyl)-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 134220-50-1 (4aS,5aS,8aR,8bS)-2-[Bis-(1-cyclohexyl-2,5-dioxo-pyrrolidin-3-yl)-methyl]-7-cyclohexyl-3-methyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 
• 134220-44-3 (4aS,5aS,8aR,8bS)-2-[Bis-(2,5-dioxo-1-phenyl-pyrrolidin-3-yl)-methyl]-3-methyl-7-phenyl-4a,5a,8a,8b-tetrahydro-pyrrolo[3',4':4,5]furo[3,2-b]pyridine-6,8-dione 

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