Product Name

  • Name

    2,3-Dimethylpyridine-N-oxide

  • EINECS
  • CAS No. 22710-07-2
  • Article Data46
  • CAS DataBase
  • Density 1 g/cm3
  • Solubility
  • Melting Point 85-93 °C
  • Formula C7H9NO
  • Boiling Point 298.1 °C at 760 mmHg
  • Molecular Weight 123.155
  • Flash Point 134.1 °C
  • Transport Information
  • Appearance
  • Safety 26-36/37/39
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 22710-07-2 (2,3-Dimethylpyridine-N-oxide)
  • Hazard Symbols IrritantXi
  • Synonyms 2,3-Lutidine,1-oxide (6CI,7CI,8CI);2,3-Dimethylpyridine 1-oxide;2,3-DimethylpyridineN-oxide;2,3-Lutidine-N-oxide;pyridine, 2,3-dimethyl-, 1-oxide;2,3-Lutidine-N-oxide;Dimethylpyridineoxide;
  • PSA 25.46000
  • LogP 1.73190

Synthetic route

2,3-Lutidine
583-61-9

2,3-Lutidine

2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

Conditions
ConditionsYield
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

2,3-Lutidine

formaldehyd
50-00-0

formaldehyd

2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

Conditions
ConditionsYield
With sulfuric acid; dihydrogen peroxide In acetic acid
2,3-Lutidine
583-61-9

2,3-Lutidine

3-chloro-benzenecarboperoxoic acid
937-14-4

3-chloro-benzenecarboperoxoic acid

2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

Conditions
ConditionsYield
With sodium sulfite In dichloromethane; Petroleum ether
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

2-hydroxymethyl-3-methyl pyridine
63071-09-0

2-hydroxymethyl-3-methyl pyridine

Conditions
ConditionsYield
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-dimethylpyridine 1-oxide

2,3-dimethyl-4-nitropyridine N-oxide
37699-43-7

2,3-dimethyl-4-nitropyridine N-oxide

Conditions
ConditionsYield
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-dimethylpyridine 1-oxide

2,3-dimethyl-4-bromopyridine N-oxide
259807-92-6

2,3-dimethyl-4-bromopyridine N-oxide

Conditions
ConditionsYield
With bromine In water at 0 - 35℃; for 6h; Temperature;92%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

5-bromo-1,3-xylene
556-96-7

5-bromo-1,3-xylene

2-(3,5-dimethylbenzyl)-3-methylpyridine 1-oxide
1151985-86-2

2-(3,5-dimethylbenzyl)-3-methylpyridine 1-oxide

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

acetic anhydride
108-24-7

acetic anhydride

2-(acetoxymethyl)-3-methylpyridine
52814-41-2

2-(acetoxymethyl)-3-methylpyridine

Conditions
ConditionsYield
for 1h; Heating;81%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

1-Heptyne
628-71-7

1-Heptyne

bis(trifluoromethanesulfonyl)amide
82113-65-3

bis(trifluoromethanesulfonyl)amide

1-(hept-1-en-2-yloxy)-2,3-dimethylpyridin-1-ium bis((trifluoromethyl)sulfonyl)amide

1-(hept-1-en-2-yloxy)-2,3-dimethylpyridin-1-ium bis((trifluoromethyl)sulfonyl)amide

Conditions
ConditionsYield
With [bis(trifluoromethanesulfonyl)imidate](triphenylphosphine)gold(I) at 20℃; for 5h;81%
...Expand
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

para-bromotoluene
106-38-7

para-bromotoluene

3-methyl-2-(4-methylbenzyl)pyridine 1-oxide
1151985-88-4

3-methyl-2-(4-methylbenzyl)pyridine 1-oxide

Conditions
ConditionsYield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; ruphos In toluene at 70℃; Inert atmosphere;76%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

trimethylsilyl cyanide
7677-24-9

trimethylsilyl cyanide

5,6-dimethylpyridine-2-carbonitrile
59146-67-7

5,6-dimethylpyridine-2-carbonitrile

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

cinnamyl acetate
103-54-8

cinnamyl acetate

C14H15N

C14H15N

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

cyclohexyltrifluoro-λ4-borane potassium salt
446065-11-8

cyclohexyltrifluoro-λ4-borane potassium salt

6-cyclohexyl-2,3-dimethylpyridine N-oxide

6-cyclohexyl-2,3-dimethylpyridine N-oxide

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

cinnamyl propionate
78761-38-3, 103-56-0

cinnamyl propionate

C14H15N

C14H15N

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

4-chloro-2,3-dimethylpyridine-N-oxide
59886-90-7

4-chloro-2,3-dimethylpyridine-N-oxide

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

phenyl isocyanate
103-71-9

phenyl isocyanate

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

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

Conditions
ConditionsYield
In xylene at 140℃; for 3.5h;40%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

p-chlorphenylisocyanate
104-12-1

p-chlorphenylisocyanate

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

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

Conditions
ConditionsYield
In xylene at 140℃; for 3.5h;38%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

p-Tolylisocyanate
622-58-2

p-Tolylisocyanate

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

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

Conditions
ConditionsYield
In xylene at 140℃; for 3.5h;36%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

para-bromotoluene
106-38-7

para-bromotoluene

2,3-dimethyl-6-(4-methylphenyl)pyridine-N-oxide
1127561-91-4

2,3-dimethyl-6-(4-methylphenyl)pyridine-N-oxide

Conditions
ConditionsYield
With palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; Inert atmosphere;34%
N-methylmaleimide
930-88-1

N-methylmaleimide

2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

(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

(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

Conditions
ConditionsYield
In toluene for 10h; Heating;25.7%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

N-(4-chlorophenyl)maleimide
1631-29-4

N-(4-chlorophenyl)maleimide

(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

(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

Conditions
ConditionsYield
In toluene for 10h; Heating;24.1%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

N-(4-bromophenyl)maleimide
13380-67-1

N-(4-bromophenyl)maleimide

(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

(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

Conditions
ConditionsYield
In toluene for 10h; Heating;22.2%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

phenyl isocyanate
103-71-9

phenyl isocyanate

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

2,3,3a,4,5,7a-hexahydro-6-methyl-2-oxo-3-phenyl-5-(N-phenylcarbamoyl)methylene-oxazolo<4,5-b>pyridine

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 110℃; for 7h;21%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

N-cyclohexylmaleimide
1631-25-0

N-cyclohexylmaleimide

(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

(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

Conditions
ConditionsYield
In toluene for 10h; Heating;20.5%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

n-butylmaleimide
2973-09-3

n-butylmaleimide

(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

(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

Conditions
ConditionsYield
In toluene for 10h; Heating;20%
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

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

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

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

N-phenyl-maleimide
941-69-5

N-phenyl-maleimide

(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

(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

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

1-(4-iodophenyl)-1H-pyrrole-2,5-dione
65833-01-4

1-(4-iodophenyl)-1H-pyrrole-2,5-dione

(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

(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

Conditions
ConditionsYield
In toluene for 10h; Heating;17.1%
phosgene
75-44-5

phosgene

2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

C8H9ClNO2(1+)*Cl(1-)

C8H9ClNO2(1+)*Cl(1-)

Conditions
ConditionsYield
In dichloromethane at 25℃; Rate constant;
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

potassium cyanide
151-50-8

potassium cyanide

4-cyano-2,3-dimethylpyridine
131895-50-6

4-cyano-2,3-dimethylpyridine

Conditions
ConditionsYield
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

2,3-dimethylpyridine 1-oxide

A

3-methoxy-2-methyl-6-nitropyridine 1-oxide
35392-67-7

3-methoxy-2-methyl-6-nitropyridine 1-oxide

B

2,3-dimethyl-4-nitropyridine N-oxide
37699-43-7

2,3-dimethyl-4-nitropyridine N-oxide

Conditions
ConditionsYield
With nitric acid In acetic acid at 80℃; for 33h;
2,3-dimethylpyridine 1-oxide
22710-07-2

2,3-dimethylpyridine 1-oxide

(2E,4Z)-5-Cyano-3-methyl-penta-2,4-dien-2-ol anion

(2E,4Z)-5-Cyano-3-methyl-penta-2,4-dien-2-ol anion

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

2,3-Dimethylpyridine-N-oxide Specification

The 2,3-Dimethylpyridine-N-oxide, with the CAS registry number 22710-07-2, has the systematic name of 2,3-dimethylpyridine 1-oxide, and it is also called Dimethylpyridineoxide. The molecular formula of the chemical is C7H9NO.

The characteristics of this chemical are as followings: (1)ACD/LogP: -0.28; (2)# of Rule of 5 Violations: 0; (3)#Freely Rotating Bonds: 0; (4)Polar Surface Area: 24.11 Å2; (5)Index of Refraction: 1.509; (6)Molar Refractivity: 36.68 cm3; (7)Molar Volume: 122.7 cm3; (8)Polarizability: 14.54×10-24cm3; (9)Surface Tension: 33.1 dyne/cm; (10)Density: 1 g/cm3; (11)Flash Point: 134.1 °C; (12)Enthalpy of Vaporization: 51.65 kJ/mol; (13)Boiling Point: 298.1 °C at 760 mmHg; (14)Vapour Pressure: 0.00229 mmHg at 25°C.

You should be cautious while dealing with this chemical. It irritates to eyes, respiratory system and skin. Therefore, you had better take the following instructions: Wear suitable protective clothing, gloves and eye/face protection, and if in case of contacting with eyes, rinse immediately with plenty of water and seek medical advice.

Addtionally, the following datas could be converted into the molecular structure:
(1)SMILES: [O-][n+]1cccc(c1C)C
(2)InChI: InChI=1/C7H9NO/c1-6-4-3-5-8(9)7(6)2/h3-5H,1-2H3
(3)InChIKey: QWLULCKKOHDCIE-UHFFFAOYAL

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