37699-43-7

Basic information

• Product Name: 4-Nitro-2,3-lutidine-N-oxide
• Synonyms: 2,3-Dimethyl-4-nitro-1-oxidopyridin-1-ium;2,3-dimethyl-4-nitro-1-oxidanidyl-pyridin-1-ium;4-Nitro-2,3-lutidine;3-DiMethyl-4-Nitropyridine N-Oxide;2,3-diMethyl-4-nitropyridin-1-iuM-1-olate;2,3-DiMethyl-4-nitropyridne-n-oxide;Lansoprazole Nitro IMpurity;2,3-dimethyl-4-nitro-pyridin1-oxide
• CAS NO: 37699-43-7
• Molecular Formula: C₇H₈N₂O₃
• Molecular Weight: 168.15
• EINECS: -0
• Product Categories: Heterocyclic Building Blocks;Heterocycles;Mutagenesis Research Chemicals;Nitric Oxide Reagents;Building Blocks;C6 to C7;Chemical Synthesis;Heterocyclic Building Blocks;Heterocycle-Pyridine series;Pyridines;Pyridines derivates;C7 and C8
• Mol File: 37699-43-7.mol
• Article Data: 17

Chemical Properties

• Melting Point: 94-98 °C(lit.)
• Boiling Point: 297.07°C (rough estimate)
• Flash Point: 197.7 °C
• Appearance: Pale yellow to yellow/Powder or Crystalline Powder
• Density: 1.3722 (rough estimate)
• Vapor Pressure: 2.4E-06mmHg at 25°C
• Refractive Index: 1.5200 (estimate)
• Storage Temp.: Room temperature.
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: -1.03±0.10(Predicted)
• BRN: 1569438
• CAS DataBase Reference: 4-Nitro-2,3-lutidine-N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Nitro-2,3-lutidine-N-oxide(37699-43-7)
• EPA Substance Registry System: 4-Nitro-2,3-lutidine-N-oxide(37699-43-7)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36
• RIDADR: 2811
• WGK Germany: 3
• RTECS: UT2807000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 37699-43-7(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Nitropyridine oxide derivative,Nitropyridine oxide derivatives show carcinogenicity and mutagenicity.

General Description

4-Nitro-2,3-lutidine N-oxide can undergo reduction in the presence of Titanium(III) chloride in 50% aqueous acetonitrile. N-hydroxylamine is formed as a by-product during the reduction reaction.

InChI:InChI=1/C7H8N2O3/c1-5-6(2)8(10)4-3-7(5)9(11)12/h3-4H,1-2H3

Synthetic route

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-methyl-4-nitropyridine N-oxide (5470-66-6) + methylmagnesium halide → 2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7)

Conditions	Yield
Stage #1: 2-methyl-4-nitropyridine N-oxide; methylmagnesium halide In tetrahydrofuran at -60℃; Inert atmosphere; Stage #2: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at -60 - 20℃; Inert atmosphere; regioselective reaction;	47%

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) + dichloromethane (75-09-2) → 2,3-diemthyl-4-nitropyridine N-oxide + 2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7)

Conditions	Yield
With sodium hydroxide; sulfuric acid; nitric acid In water

2,3-dimethylpyridine 1-oxide (22710-07-2) + concentrated H2 SO4 + sodium carbonate (497-19-8) → 4-carboxy-2-nitropyridine N-oxide (2403-02-3) + 2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7)

Conditions	Yield
With nitric acid

2,3-Lutidine (583-61-9) → 2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: dihydrogen peroxide; acetic acid / 24 h / Reflux 2: nitric acid; sulfuric acid / 24 h / 90 °C View Scheme
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / chloroform / 18 h / 20 °C 2: nitric acid; sulfuric acid / 95 °C View Scheme
Multi-step reaction with 2 steps 1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 2: sulfuric acid; nitric acid / water / 5 h / 95 °C View Scheme

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → 4-chloro-2,3-dimethylpyridine-N-oxide (59886-90-7)

Conditions	Yield
With acetyl chloride In ethanol at 65℃; for 5h;	100%
With hydrogenchloride; sodium chloride; benzyltri(n-butyl)ammonium chloride In water; acetonitrile for 12h; Heating / reflux;	98.5%
Stage #1: 2,3-dimethyl-4-nitropyridine N-oxide With hydrogenchloride; benzyltri(n-butyl)ammonium chloride; sodium chloride In water; acetonitrile for 12h; Heating / reflux; Stage #2: In water; acetonitrile pH=9;	98.5%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + Cyclopropylmethanol (2516-33-8) → 4-Cyclopropylmethoxy-2,3-dimethyl-pyridine 1-oxide (206990-47-8)

Conditions	Yield
With benzyltri(n-butyl)ammonium chloride; potassium hydrogencarbonate In acetonitrile for 24h; Heating;	100%

methanol (67-56-1) + 2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → 4-methoxy-2,3-dimethylpyridine 1-oxide (102625-96-7)

Conditions	Yield
With potassium carbonate for 2h; Heating;	99%
With potassium carbonate at 0 - 65℃; for 4h;	83%
With potassium carbonate for 20h; Heating;	82%
With potassium carbonate In acetonitrile at 0℃; Reflux;	47%
With sodium methylate at 40℃; for 16h;

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + acetyl chloride (75-36-5) → 4-chloro-2,3-dimethylpyridine-N-oxide (59886-90-7)

Conditions	Yield
Stage #1: 2,3-dimethyl-4-nitropyridine N-oxide; acetyl chloride In ethanol at 65℃; Large scale reaction; Stage #2: With sodium hydroxide In ethanol; water; toluene pH=7.5 - 8.5; Large scale reaction;	96%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → 2,3-dimethyl-4-nitropyridine (68707-69-7)

Conditions	Yield
Stage #1: 2,3-dimethyl-4-nitropyridine N-oxide With phosphorus trichloride In dichloromethane at -20 - 15℃; for 1h; Stage #2: With sodium hydroxide; water In dichloromethane at -78℃;	95%
With phosphorus trichloride In dichloromethane -20 degC, 15 min, r.t., 15 min;	92%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 2,2,2-trifluoroethanol (75-89-8) → 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide (103577-61-3)

Conditions	Yield
With potassium tert-butylate at 50 - 60℃; for 42h;	94%
With potassium tert-butylate; palladium dichloride In dichloromethane at 83 - 88℃; for 6 - 8h;	95 - 97 %Chromat.
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In water; butanone at 20℃; Concentration; Temperature; Time; Pressure;

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → 4-amino-2,3-dimethylpyridine (122475-57-4)

Conditions	Yield
With hydrogen; acetic acid; palladium on activated charcoal at 60℃; under 2585.7 Torr; for 12h;	94%
With iron; acetic acid In water	76%
With iron In acetic acid at 100℃; for 2h;	56%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → 2,3-dimethyl-4-bromopyridine N-oxide (259807-92-6)

Conditions	Yield
With Acetyl bromide In chloroform for 1h; Heating;	93%
With hydrogen bromide In acetic acid at 100℃; for 48h; Heating;

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → 3-methyl-4-nitro-2-pyridinecarboxaldehyde-N-oxide (147440-89-9)

Conditions	Yield
With selenium(IV) oxide In 1,4-dioxane for 48h; Heating;	88%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 2,2,3,3-tetrafluoropropanol (76-37-9) → 2,3-dimethyl-4-(2,2,3,3-tetrafluoropropoxy)pyridine-1-oxide (103577-57-7)

Conditions	Yield
With potassium tert-butylate at 50 - 60℃;	86%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + propargyl alcohol (107-19-7) → 2,3-Dimethyl-4-prop-2-ynyloxy-pyridine 1-oxide (206990-49-0)

Conditions	Yield
With benzyltri(n-butyl)ammonium chloride; potassium carbonate In acetonitrile at 90℃; for 3h;	86%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 5-decyne (1942-46-7) → 6-(5,6-dimethyl-4-nitropyridin-2-yl)decan-5-one

Conditions	Yield
With 1,1,1,3',3',3'-hexafluoro-propanol; 9-(2-mesityl)-10-methylacridinium perchlorate In acetone at 50℃; for 48h; Schlenk technique; Glovebox; Inert atmosphere; Sealed tube; Irradiation; regioselective reaction;	86%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → C7H10N2O + 4-amino-2,3-dimethylpyridine (122475-57-4)

Conditions	Yield
With hydrogenchloride; titanium(III) chloride In water; acetonitrile at 20℃; for 1h;	A 17% B 83%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 2,2,3,3,4,4,5,5-octafluoropentan-1-ol (355-80-6) → 2,3-Dimethyl-4-(2,2,3,3,4,4,5,5-octafluoro-pentyloxy)-pyridine 1-oxide (132332-23-1)

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃;	81%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 2,2,3,3,3-pentafluoropropyl alcohol (422-05-9) → 2,3-Dimethyl-4-(2,2,3,3,3-pentafluoropropoxy)pyridine N-oxide (103577-60-2)

Conditions	Yield
With N,N,N,N,N,N-hexamethylphosphoric triamide; potassium carbonate In butanone at 70 - 80℃; for 108h;	74%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 2,2,3,3,4,4,4-heptafluorobutanol (375-01-9) → 2,3-Dimethyl-4-(2,2,3,3,4,4,4-heptafluorobutoxy)pyridine N-oxide (132332-22-0)

Conditions	Yield
With potassium carbonate In acetonitrile at 90 - 100℃; for 41h;	73%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + diphenyl acetylene (501-65-5) → (5,6-dimethyl-4-nitropyridin-2-yl)(phenyl)methanone

Conditions	Yield
Stage #1: 2,3-dimethyl-4-nitropyridine N-oxide; diphenyl acetylene With tetrafluoroboric acid; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 50℃; for 24h; Schlenk technique; Glovebox; Inert atmosphere; Irradiation; Stage #2: In acetonitrile at 50℃; for 12h; Schlenk technique; Glovebox; Irradiation;	67%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 5-decyne (1942-46-7) → 1-(5,6-dimethyl-4-nitropyridin-2-yl)pentan-1-one

Conditions	Yield
With tetrafluoroboric acid; oxygen; 9-(2-mesityl)-10-methylacridinium perchlorate In acetonitrile at 50℃; for 12h; Schlenk technique; Irradiation;	65%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + benzyl alcohol (100-51-6) → 4-(benzyloxy)-2,3-dimethylpyridin-N-oxide (102127-29-7)

Conditions	Yield
With benzyltri(n-butyl)ammonium chloride; potassium carbonate In acetonitrile at 90℃; for 20h;	57%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + Methanesulfonic anhydride (7143-01-3) → 2-methanesulfonyloxymethyl-3-methyl-4-nitropyridine methanesulfonate

Conditions	Yield
In dichloromethane for 12h; Heating;	54%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + 2-methoxy-ethanol (109-86-4) → 4-(2-Methoxy-ethoxy)-2,3-dimethyl-pyridine 1-oxide (206990-48-9)

Conditions	Yield
With potassium carbonate for 20h; Heating;	53%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + acetic anhydride (108-24-7) → (3-methyl-4-nitropyridin-2-yl)methyl acetate (166521-98-8)

Conditions	Yield
at 100℃; for 3h;	49%
at 100℃; for 1.5h;	11.5 g

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + p-toluenesulfonylanhydride (4124-41-8) → 3-methyl-4-nitro-2-(4-toluenesulfonyloxymethyl)pyridine 4-toluenesulfonate

Conditions	Yield
In dichloromethane for 12h; Heating;	37%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) → 4-chloro-2-chloromethyl-3-methylpyridine

Conditions	Yield
Stage #1: 2,3-dimethyl-4-nitropyridine N-oxide With trichlorophosphate In dichloromethane at 20℃; for 24h; Stage #2: With triethylamine In dichloromethane at 0℃; for 0.5h;	20%
Multi-step reaction with 4 steps 1: 75 percent / phosphorus oxychloride / CH2Cl2 / 20 °C 2: 63 percent / 3 h / 100 °C 3: 78 percent / aq. hydrochloric acid / 24 h / 20 °C 4: 43 percent / thionyl chloride / CH2Cl2 / 1 h / Heating View Scheme
Multi-step reaction with 2 steps 1: 75 percent / phosphorus oxychloride / CH2Cl2 / 20 °C 2: 37 percent / phosphorus oxychloride; triethylamine / CH2Cl2 / 2 h / 20 °C View Scheme

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + trimethylsilyl cyanide (7677-24-9) → 4-chloro-5,6-dimethyl-2-cyanopyridine (1323393-00-5)

Conditions	Yield
With chloroformic acid ethyl ester In 1,2-dichloro-ethane at -5 - 40℃;	18%

2,3-dimethyl-4-nitropyridine N-oxide (37699-43-7) + ethanol (64-17-5) → 4-ethoxy-2,3-dimethylpyridine N-oxide (1034065-92-3)

Conditions	Yield
With sodium ethanolate at 70℃; for 24h; Heating;

Upstream product

• 22710-07-2 2,3-dimethylpyridine 1-oxide 
• 75-09-2 dichloromethane 
• 583-61-9 2,3-Lutidine 
• 5470-66-6 2-methyl-4-nitropyridine N-oxide 
• 497-19-8 sodium carbonate 

Downstream Products

• 102127-29-7 4-(benzyloxy)-2,3-dimethylpyridin-N-oxide 
• 124473-12-7 2-chloromethyl-3-methyl-4-methoxypyridine 
• 206990-53-6 [4-(2-Methoxy-ethoxy)-3-methyl-pyridin-2-yl]-methanol 
• 102137-66-6 (4-Benzyloxy-3-methyl-pyridin-2-yl)-methanol 
• 768319-30-8 4-Benzyloxy-2-chloromethyl-3-methyl-pyridine 
• 102127-30-0 Acetic acid 4-benzyloxy-3-methyl-pyridin-2-ylmethyl ester 
• 102625-62-7 5-difluoromethoxy-2-[(4,5-dimethoxy-3-methyl-pyridin-2-yl)methylthio]-1H-benzimidazole 
• 97966-86-4 2,2-difluoro-6-[(4-methoxy-3-methyl-2-pyridyl)methylsulfinyl]-5H-[1,3]-dioxolo-[4,5-f]benzimidazole 
• 103577-61-3 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide 
• 59886-90-7 4-chloro-2,3-dimethylpyridine-N-oxide 
• 117976-47-3 LY 307640 sulfone 
• 117977-21-6 rabeprazole sulfide 
• 924663-37-6 2-[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole 
• 152402-98-7 2-[(4-nitro-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzoimidazole 

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