Conditions | Yield |
---|---|
With sodium at 70℃; for 24h; Heating; | 99% |
With potassium tert-butylate at 20℃; for 1h; | 93% |
With potassium tert-butylate at 20℃; for 1h; | 93% |
Conditions | Yield |
---|---|
In methanol for 1h; Concentration; Reflux; | 95.36% |
In methanol; dimethyl sulfoxide at 20℃; Rate constant; formation of Meisenheimer complex; | |
In methanol for 6h; Heating; |
Conditions | Yield |
---|---|
Stage #1: methanol With N-benzyl-trimethylammonium hydroxide for 0.166667h; Neat (no solvent); Stage #2: 2-iodo-5-nitropyridine at 20℃; for 0.0833333h; Neat (no solvent); | 95% |
methanol
2-chloro-5-nitropyridine
sodium methylate
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
Reflux; | 92.1% |
2-methoxypyridine N-oxide hydrochloride
A
2-methoxy-5-nitropyridine
B
2-methoxy-4-nitropyridine N-oxide
C
2-methoxy-5-nitropyridine N-oxide
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid In sulfuric acid at 90 - 100℃; for 3h; | A 20% B 62% C 11% |
2-methoxy-pyridine-5-boronic acid
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
With N–nitrosuccinimide; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate In acetonitrile at 20℃; for 19h; Inert atmosphere; Irradiation; | 35% |
2-methoxypyridine N-oxide
A
2-methoxy-5-nitropyridine
B
2-methoxy-4-nitropyridine
C
2-methoxy-4-nitropyridine N-oxide
D
2-methoxy-5-nitropyridine N-oxide
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 75℃; for 1.5h; | A n/a B n/a C 30% D 2.9 g |
With sulfuric acid; nitric acid at 75℃; for 1.5h; Title compound not separated from byproducts; | A n/a B n/a C 6.4 g D 2.9 g |
With sulfuric acid; nitric acid at 75℃; for 1.5h; | A n/a B n/a C 6.4 g D 2.9 g |
Conditions | Yield |
---|---|
With sulfuric acid; nitric acid at 70℃; Rate constant; other concentration of H2SO4; | |
With sulfuric acid; nitric acid |
Conditions | Yield |
---|---|
With methanol; water; sodium sulfite |
2-iodo-5-nitropyridine
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
With methanol; sodium methylate |
6-ethoxy-2-(5-nitro-[2]pyridylmercapto)-[3]pyridylamine
A
2-methoxy-5-nitropyridine
B
6-ethoxy-2-methylsulfanyl-[3]pyridylamine
Conditions | Yield |
---|---|
With potassium hydroxide anschliessendes Behandeln mit CH3I; |
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 20℃; Rate constant; formation of Meisenheimer complex; |
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 20℃; Rate constant; formation of Meisenheimer complex; |
2-(3-methylphenoxy)-5-nitropyridine
sodium methylate
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 20℃; Rate constant; formation of Meisenheimer complex; |
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 20℃; Rate constant; formation of Meisenheimer complex; |
2-(m-chlorophenoxy)-5-nitropyridine
sodium methylate
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 20℃; Rate constant; formation of Meisenheimer complex; |
sodium methylate
2-(m-nitrophenoxy)-5-nitropyridine
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
In methanol; dimethyl sulfoxide at 20℃; Rate constant; formation of Meisenheimer complex; |
methanol
3-Nitro-6-(methylsulfonyl)pyridine
ammonia
A
5-nitro-pyridin-2-ylamine
B
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
at 37℃; |
methyl iodide
A
2-methoxy-5-nitropyridine
B
1-methyl-5-nitro-2(1H)-pyridone
Conditions | Yield |
---|---|
With methanol |
Conditions | Yield |
---|---|
With sodium hydride at 23℃; for 16h; | 102 mg |
Conditions | Yield |
---|---|
at 65℃; for 20h; | 115 mg |
5-Hydroxyaminopyridine-2-sulfonic acid
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aq. KMnO4 / 10 h / 20 °C 2: 115 mg / 20 h / 65 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: aqueous hydrofluoric acid / Behandeln der Reaktionsloesung mit Natriumnitrit View Scheme | |
Multi-step reaction with 3 steps 1: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 - 6 °C 2: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Reflux 3: methanol / 1 h / Reflux View Scheme | |
Multi-step reaction with 3 steps 1: sodium hydroxide / Reflux 2: trichlorophosphate / N,N-dimethyl-formamide / Reflux 3: Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / 1,2-dichloro-ethane / 10 h / 58 °C 2: hydrogenchloride; sodium nitrite / water / 0.67 h / 0 - 6 °C 3: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Reflux 4: methanol / 1 h / Reflux View Scheme | |
Multi-step reaction with 4 steps 1: nitric acid; sulfuric acid / 80 °C 2: sodium hydroxide / Reflux 3: trichlorophosphate / N,N-dimethyl-formamide / Reflux 4: Reflux View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: trichlorophosphate / N,N-dimethyl-formamide / 2 h / 20 °C / Reflux 2: methanol / 1 h / Reflux View Scheme | |
Multi-step reaction with 2 steps 1: trichlorophosphate / N,N-dimethyl-formamide / Reflux 2: Reflux View Scheme |
Conditions | Yield |
---|---|
With potassium fluoride; polymethylhydrosiloxane; palladium diacetate In tetrahydrofuran at 20℃; for 0.5h; | 100% |
With cyclohexa-1,4-diene; 5%-palladium/activated carbon In methanol at 120℃; for 0.0833333h; Microwave irradiation; | 99% |
With iron; calcium chloride In ethanol for 2h; Heating; | 97% |
2-methoxy-5-nitropyridine
(4-chlorophenoxy)acetonitrile
2-(6-methoxy-3-nitropyridin-2-yl)acetonitrile
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran at -20℃; for 35h; Inert atmosphere; | 95% |
With potassium tert-butylate In tetrahydrofuran at -10℃; for 3.5h; | 94% |
With potassium tert-butylate In tetrahydrofuran at -10℃; for 3h; | 86% |
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
With sodium tetrahydroborate; sodium methylate In methanol at 25℃; | 92% |
Conditions | Yield |
---|---|
With N,N-dimethyl-formamide; trichlorophosphate at 85℃; for 8h; | 91% |
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 5h; | 91% |
2-methoxy-5-nitropyridine
Conditions | Yield |
---|---|
With sodium hydroxide In dimethyl sulfoxide at 20 - 25℃; for 5h; | 90% |
2-methoxy-5-nitropyridine
ethyl chlorofluoroacetate
Conditions | Yield |
---|---|
Stage #1: 2-methoxy-5-nitropyridine; ethyl chlorofluoroacetate With potassium tert-butylate In N,N-dimethyl-formamide at -42℃; for 0.75h; Inert atmosphere; Stage #2: With Selectfluor In N,N-dimethyl-formamide at -42℃; for 1h; Inert atmosphere; | 90% |
(5-methyl-pyridin-2-yl)amine
2-methoxy-5-nitropyridine
carbon monoxide
Conditions | Yield |
---|---|
With selenium(IV) oxide; triethylamine In toluene at 130℃; under 22501.8 Torr; | 89% |
Conditions | Yield |
---|---|
With selenium(IV) oxide; triethylamine In toluene at 130℃; under 22501.8 Torr; | 88% |
2-methoxy-5-nitropyridine
6-methoxy-3-nitropyridin-2-amine
Conditions | Yield |
---|---|
With O-Methylhydroxylamin; potassium tert-butylate; zinc(II) chloride In dimethyl sulfoxide Ambient temperature; | 87% |
With potassium permanganate; ammonia at -33℃; for 5h; | 75% |
With N,N-tetramethylene-thiocarbamoyl-sulphenamide | 42% |
Conditions | Yield |
---|---|
With carbon monoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; selenium In toluene at 160℃; under 22502.3 Torr; for 4h; | 87% |
O-Methylhydroxylamin
2-methoxy-5-nitropyridine
zinc(II) chloride
6-methoxy-3-nitropyridin-2-amine
Conditions | Yield |
---|---|
With ammonium chloride; potassium tert-butylate In dimethyl sulfoxide | 87% |
Conditions | Yield |
---|---|
With selenium(IV) oxide; triethylamine In toluene at 130℃; under 22501.8 Torr; | 85% |
Conditions | Yield |
---|---|
Stage #1: 2-methoxy-5-nitropyridine; 2-chloro-propanoic acid, ethyl ester With potassium tert-butylate In N,N-dimethyl-formamide at -42℃; for 0.75h; Inert atmosphere; Stage #2: With Selectfluor In N,N-dimethyl-formamide at -42℃; for 1h; Inert atmosphere; | 85% |
2-methoxy-5-nitropyridine
ethyl 1,1-dichloroacetate
Chloro-(6-methoxy-3-nitro-pyridin-2-yl)-acetic acid ethyl ester
Conditions | Yield |
---|---|
With potassium tert-butylate In N,N-dimethyl-formamide for 0.0833333h; -5 to 0 deg C; | 84% |
Conditions | Yield |
---|---|
With carbon monoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; selenium In toluene at 160℃; under 22502.3 Torr; for 4h; | 84% |
Conditions | Yield |
---|---|
With selenium; triethylamine at 60℃; for 10h; | 84% |
With selenium; triethylamine In acetone at 20℃; under 760.051 Torr; for 15h; | 77% |
2-methoxy-5-nitropyridine
chloromethyl phenyl sulfone
6-Methoxy-3-nitro-2-[(phenylsulfonyl)methyl]-pyridine
Conditions | Yield |
---|---|
With potassium tert-butylate; dimethyl sulfoxide at 20℃; for 0.416667h; | 83% |
In tetrahydrofuran; acetic acid | 80% |
Stage #1: 2-methoxy-5-nitropyridine; chloromethyl phenyl sulfone With potassium tert-butylate In tetrahydrofuran at -40℃; for 0.75h; Stage #2: With acetic acid In tetrahydrofuran at -40℃; | 80% |
Stage #1: chloromethyl phenyl sulfone With potassium tert-butylate In N,N-dimethyl-formamide at -40℃; for 0.00833333h; Inert atmosphere; Stage #2: 2-methoxy-5-nitropyridine In N,N-dimethyl-formamide at -40℃; for 0.0833333h; Inert atmosphere; | 67% |
With potassium tert-butylate In tetrahydrofuran at -65 - -20℃; for 1h; |
2-methoxy-5-nitropyridine
cyanomethylenetrimethylammonium iodide
2-(6-methoxy-3-nitropyridin-2-yl)acetonitrile
Conditions | Yield |
---|---|
With sodium hydride In dimethyl sulfoxide at 20 - 25℃; for 5h; | 83% |
Conditions | Yield |
---|---|
With selenium(IV) oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene at 130℃; under 22501.8 Torr; for 4h; | 83% |
Conditions | Yield |
---|---|
Stage #1: 1-ethynyl-4-fluorobenzene With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.566667h; Inert atmosphere; Stage #2: 2-methoxy-5-nitropyridine In tetrahydrofuran; hexane at -70℃; for 1h; Inert atmosphere; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; hexane at -70 - 20℃; for 1.33333h; Inert atmosphere; | 83% |
Conditions | Yield |
---|---|
With selenium(IV) oxide; triethylamine In toluene at 130℃; under 22501.8 Torr; | 82% |
Conditions | Yield |
---|---|
With carbon monoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; selenium In toluene at 160℃; under 22502.3 Torr; for 4h; | 81% |
Conditions | Yield |
---|---|
With carbon monoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; selenium In toluene at 160℃; under 22502.3 Torr; for 4h; | 80% |
Conditions | Yield |
---|---|
In water | 78% |
Conditions | Yield |
---|---|
Stage #1: phenylacetylene With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium In tetrahydrofuran; hexane at -70℃; for 0.566667h; Inert atmosphere; Stage #2: 2-methoxy-5-nitropyridine In tetrahydrofuran; hexane at -70℃; for 1h; Inert atmosphere; Stage #3: With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran; hexane at -70 - 20℃; for 1.33333h; Inert atmosphere; | 77% |
The 2-Methoxy-5-nitropyridine is also its IUPAC name of this chemical. With cas registry number of 5446-92-4, this chemical belongs to a kind of classes in blocks; Pyridines; Pyridine; Pyridines, Pyrimidines, Purines and Pteredines; Pyridines derivates; Boronic Acid; C6; Heterocyclic Building Blocks. Its EINECS registry number is 226-661-7 with appearance of very slightly yellow adhering powder.
Physical properties about this chemical are: (1)ACD/LogP: 1.33; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.33; (4)ACD/LogD (pH 7.4): 1.33; (5)ACD/BCF (pH 5.5): 6.02; (6)ACD/BCF (pH 7.4): 6.02; (7)ACD/KOC (pH 5.5): 125.85; (8)ACD/KOC (pH 7.4): 125.85; (9)#H bond acceptors: 5; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 2; (12)Index of Refraction: 1.546; (13)Molar Refractivity: 37.56 cm3; (14)Molar Volume: 118.5 cm3; (15)Surface Tension: 49 dyne/cm; (16)Density: 1.3 g/cm3; (17)Flash Point: 110.4 °C; (18)Enthalpy of Vaporization: 47.65 kJ/mol; (19)Boiling Point: 258.9 °C at 760 mmHg; (20)Vapour Pressure: 0.0216 mmHg at 25°C.
Preparation of 2-Methoxy-5-nitropyridine: this chemical can be made by reaction of 2-chloro-5-nitro-pyridine with methanol using reagent NaH, solvent tetrahydrofuran under Ambient temperature. The reaction time is 1 hour with 82% yield.
Uses of 2-Methoxy-5-nitropyridine: it can be used to prepare 6-methoxy-pyridin-3-ylamine using reagents iron-powder, acetic acid, and aqueous methanol.
When you are using this chemical, please be cautious about it as the following:
This chemical is irritating to eyes, respiratory system and skin. Wear suitable protective clothing, gloves and eye/face protection during using it. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
You can still convert the following datas into molecular structure:
(1)Canonical SMILES: COC1=NC=C(C=C1)[N+](=O)[O-];
(2)InChI: InChI=1S/C6H6N2O3/c1-11-6-3-2-5(4-7-6)8(9)10/h2-4H,1H3;
(3)InChIKey: WUPLOZFIOAEYMG-UHFFFAOYSA-N
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