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

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

Uses

Used in Chemical Synthesis:
4-Nitro-2,3-lutidine-N-oxide is used as a chemical intermediate for the synthesis of various compounds due to its reactivity in reduction reactions. The formation of N-hydroxylamine as a by-product makes it a valuable component in the creation of different chemical products.
Used in Research and Development:
In the field of research and development, 4-Nitro-2,3-lutidine-N-oxide serves as a crucial compound for studying the effects of nitropyridine oxide derivatives, which have been found to exhibit carcinogenicity and mutagenicity. This knowledge aids in understanding the potential risks and applications of these compounds in various industries.

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 
• 497-19-8 sodium carbonate 
• 583-61-9 2,3-Lutidine 
• 5470-66-6 2-methyl-4-nitropyridine N-oxide 

Downstream Products

• 68707-69-7 2,3-dimethyl-4-nitropyridine 
• 103312-62-5 2-[(4-chloro-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzoimidazole 
• 168167-49-5 (3-methyl-4-nitropyridin-2-yl)methanol 
• 152402-98-7 2-[(4-nitro-3-methylpyridin-2-yl)methylsulfanyl]-1H-benzoimidazole 
• 924663-37-6 2-[(4-(3-methoxypropoxy)-3-methyl-pyridin-2-yl-1-oxide)methylsulfonyl]-1H-benzoimidazole 
• 117977-21-6 rabeprazole sulfide 
• 117976-47-3 LY 307640 sulfone 
• 103577-61-3 2,3-dimethyl-4-(2,2,2-trifluoroethoxy)-pyridine N-oxide 
• 59886-90-7 4-chloro-2,3-dimethylpyridine-N-oxide 
• 122475-57-4 4-amino-2,3-dimethylpyridine 
• 1329793-61-4 C₇H₈ClNO₂ 
• 253345-80-1 C₉H₁₀F₃NO₂*ClH 
• 112525-75-4 2-acetoxymethyl-3-methyl-4-(2,2,2-trifluoroethoxy)pyridine 
• 675198-19-3 [4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanol hydrochloride 

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